Alkaloids are a group of naturally occurring chemical compounds, that contain

[2]
mostly basic nitrogen atoms. This group also includes some related compounds with neutral and
[3]
even weakly acidic properties. Some synthetic compounds of similar structure are also attributed to
[4]
alkaloids. In addition to carbon, hydrogen and nitrogen, alkaloids may also
[5]
contain oxygen, sulfur and more rarely other elements such aschlorine, bromine, and phosphorus.
Alkaloids are produced by a large variety of organisms, including bacteria, fungi, plants, and animals,
and are part of the group of natural products(also called secondary metabolites). Many alkaloids can
be purified from crude extracts by acid-base extraction. Many alkaloids are toxic to other organisms.
They often have pharmacological effects and are used as medications, as recreational drugs, or
in entheogenic rituals. Examples are the local anesthetic and stimulant cocaine; the
[6]
psychedelic psilocin; the stimulant caffeine; nicotine; the analgesic morphine; the
antibacterialberberine; the anticancer compound vincristine; the antihypertension agent reserpine; the
cholinomimeric galantamine; the spasmolysis agentatropine; the vasodilator vincamine; the antiarhythmia compound quinidine; the anti-asthma therapeutic ephedrine; and the antimalarial
drugquinine. Although alkaloids act on a diversity of metabolic systems in humans and other animals,
[7]
they almost uniformly invoke a bitter taste.
The boundary between alkaloids and other nitrogen-containing natural compounds is not clear[8]
cut. Compounds like amino acid peptides,proteins, nucleotides, nucleic acid, amines,
[2]
and antibiotics are usually not called alkaloids. Natural compounds containing nitrogen in
theexocyclic position (mescaline, serotonin, dopamine, etc.) are usually attributed to amines rather
[9]
[10][11][12]
than alkaloids. Some authors, however, consider alkaloids a special case of amines.

The first individual alkaloid, morphine, was isolated in 1804 from poppy (Papaver somniferum

The name "alkaloids" (German: Alkaloide) was introduced in 1819 by the German chemist Carl
Friedrich Wilhelm Meiner, and is derived from late Latin rootLatin: alkali (which, in turn, comes from
[nb 1]
the Arabic al-qalw "ashes of plants") and the suffix Greek: - "like".
However, the term
came into wide use only after the publication of a review article by Oscar Jacobsen in the chemical
[13][14]
dictionary of Albert Ladenburg in the 1880s.
[15]

There is no unique method of naming alkaloids. Many individual names are formed by adding the
[16]
suffix "ine" to the species or genus name. For example,atropine is isolated from the plant Atropa
[5]
belladonna, strychnine is obtained from the seed of Strychnine tree (Strychnos nux-vomica L.). If
several alkaloids are extracted from one plant then their names often contain suffixes "idine", "anine",
"aline", "inine", etc. There are also at least 86 alkaloids containing the root "vin" (extracted from
[17]
the Vinca plant).

History[edit]

Friedrich Sertrner, the German chemist who first isolated morphine from opium.

Alkaloid-containing plants have been used by humans since ancient times for therapeutic and
recreational purposes. For example, medicinal plants have been known in the Mesopotamia at least
[18]
around 2000 BC. The Odyssey ofHomer referred to a gift given to Helen by the Egyptian queen, a
[19]
drug bringing oblivion. It is believed that the gift was an opium-containing drug. A Chinese book on
houseplants written in 1st3rd centuries BC mentioned a medical use ofEphedra and opium
[20]
[21]
poppies. Also, coca leaves have been used by South American Indians since ancient times.
Extracts from plants containing toxic alkaloids, such as aconitine and tubocurarine, were used since
[18]
antiquity for poisoning arrows.
Studies of alkaloids began in the 19th century. In 1804, the German chemist Friedrich
Sertrner isolated from opium a "soporific principle" (Latin: principium somniferum), which he called
"morphium" in honor of Morpheus, the Greek god of dreams; in German and some other CentralEuropean languages, this is still the name of the drug. The term "morphine", used in English and
French, was given by the French physicist Joseph Louis Gay-Lussac).
A significant contribution to the chemistry of alkaloids in the early years of its development was made
by the French researchers Pierre Joseph Pelletier and Joseph Bienaim Caventou, who
discovered quinine (1820) and strychnine (1818). Several other alkaloids were discovered around that
time,
including xanthine (1817), atropine (1819), caffeine (1820), coniine (1827), nicotine (1828), colchicine
[22]
(1833), sparteine (1851), and cocaine (1860).
The first complete synthesis of an alkaloid was achieved in 1886 by the German chemist Albert
Ladenburg. He produced coniine by reacting 2-methylpyridine with acetaldehyde and reducing the
[23][24]
resulting 2-propenyl pyridine with sodium.
The development of the chemistry of alkaloids was
accelerated by the emergence of spectroscopic and chromatographic methods in the 20th century, so
[25]
that by 2008 more than 12,000 alkaloids had been identified.

Bufotenin, an alkaloid from some toads, contains an indolecore and is produced in living organisms from the amino
acidtryptophan.

Classification[edit]

The nicotine molecule contains both pyridine (left) andpyrrolidine rings (right).

Compared with most other classes of natural compounds, alkaloids are characterized by a great
[26]
structural diversity and there is no uniform classification of alkaloids. First classification methods
have historically combined alkaloids by the common natural source, e.g., a certain type of plants. This
classification was justified by the lack of knowledge about the chemical structure of alkaloids and is
[5][27]
now considered obsolete.
More recent classifications are based on similarity of the carbon skeleton (e.g., indole-, isoquinoline-,
[5]
and pyridine-like) or biogenetic precursor (ornithine, lysine,tyrosine, tryptophan, etc.). However, they
[26]
require compromises in borderline cases; for example, nicotine contains a pyridine fragment
[28]
from nicotinamide andpyrrolidine part from ornithine and therefore can be assigned to both
[29]
classes.
Alkaloids are often divided into the following major groups:

[30]

1. "True alkaloids", which contain nitrogen in the heterocycle and originate from amino
[31]
acids. Their characteristic examples are atropine, nicotine, andmorphine. This group also
[32]
includes some alkaloids that besides nitrogen heterocycle contain terpene (e.g., evonine )
[33]
or peptide fragments (e.g.ergotamine ). This group also includes piperidine
[34]
[35]
alkaloids coniine and coniceine although they do not originate from amino acids.
2. "Protoalkaloids", which contain nitrogen and also originate from amino acids.
include mescaline, adrenaline and ephedrine.

[31]

Examples

3. Polyamine alkaloids derivatives of putrescine, spermidine, and spermine.

4. Peptide and cyclopeptide alkaloids.

[36]
[37]

5. Pseudalkaloids alkaloid-like compounds that do not originate from amino acids. This
[38]
group includes, terpene-like and steroid-like alkaloids, as well as purine-like alkaloids such
[39]
as caffeine, theobromine, theacrine and theophylline. Some authors classify as
pseudoalkaloids such compounds such asephedrine and cathinone. Those originate from the
amino acid phenylalanine, but acquire their nitrogen atom not from the amino acid but
[39][40]
throughtransamination.
Some alkaloids do not have the carbon skeleton characteristic of their group. So, galantamine and
homoaporphines do not contain isoquinoline fragment, but are, in general, attributed to isoquinoline
[41]
alkaloids.
Main classes of monomeric alkaloids are listed in the table below:

Class

Major

Main synthesis steps

Examples

groups

Alkaloids with nitrogen heterocycles (true alkaloids)

Pyrrolidin
ederivativ
[42]
es

Ornithine or arginine putrescine

1
N-methylputrescine N-methyl- [43]
pyrroline

Atropine
group
Tropane
derivative
[45]
s

Cuscohygrine, hygrine, hygroline,

[42][44]
stachydrine

Atropine, scopolamine, hyoscyamine

Substitution

[4

2][45][46]

in positions
3, 6 or 7

Cocaine
group
Substitution

Ornithine or arginine putrescine

1
N-methylputrescine N-methyl- [43]
pyrroline

Cocaine, ecgonine

[45][47]

in positions 2
and 3

Nonesters

Retronecine, heliotridine,
[48][49]
laburnine

Complex
In
esters of
Pyrrolizidi
plants: ornithine or arginine putresci
[48]
monocarb
[43 Indicine, lindelophin, sarracine
nederivati
ne homospermidine retronecine
oxylic
[48]
]
ves
acids

Macrocycl
ic diesters

Platyphylline, trichodesmine

[48]

1In fungi: L-proline + L-homoserine N- Loline, N-formylloline, N-acetylloline[52]

aminopyrr
(3-amino-3-carboxypropyl)proline
olizidines

(lolines)

7]

Indolizidi
nederivati
[62]
ves

[50][51]

Piperidin
ederivativ
[53]
es

Quinolizi
dinederiv
[56][5
atives

norloline

Lysine cadaverine [54]

piperideine

Sedamine, lobeline,
[34][55]
anaferine, piperine

Octanoic acid coniceine

[35]
coniine

Coniine, coniceine

[35]

Lupinine
group

Lupinine, nupharidin

Cytisine g
roup

Cytisine

[56]

[56]

Sparteine Lysine cadaverine [58]

group
piperideine

Sparteine, lupanine, anahygrine

Matrine gr
oup

Matrine, oxymatrine,
[56][59][60]
allomatridine

Ormosani
ne group

Ormosanine, piptantine

[56]

[56][61]

Lysine -semialdehyde of [64]

aminoadipic acid pipecolic acid 1 Swainsonine, castanospermine
[63]
indolizidinone

Simple
Pyridined
derivative Nicotinic acid dihydronicotinic acid
erivatives
[67]
s of
1,2-dihydropyridine
[65][66]
pyridine

Trigonelline, ricinine, arecoline

[65][68]

Isoquinoli
ne deriva
tives and
related
[
alkaloids
70]

Polycyclic
nonconde
nsing
pyridine
derivative
s

Nicotine, nornicotine, anabasine,

[65][68]
anatabine

Polycyclic
condense
d pyridine
derivative
s

Actinidine, gentianine, pediculinine

Sesquiter
pene pyri
[12]
dine
Nicotinic acid, isoleucine
derivative
s

Evonine, hippocrateine,
[66][67]
triptonine

Simple
derivative
s of
isoquinoli
[71]
ne

Salsoline, lophocerine

Derivative
s of 1N-methylcoridaldine,
and 3[74]
noroxyhydrastinine
isoquinoli
Tyrosine or phenylalanine dopamine
[74]
nes
or tyramine (for alkaloids
[72][73]
Amarillis)
Derivative
s of 1and 4phenyltetr
ahydroiso
quinolines

Cryptostilin

[71][75]

[71]

Derivative

Ancistrocladine

[76]

[70][71]

[69]

s of 5naftilisoquinoli
[76]
ne

Derivative
s of 1and 2benzylizoquinoli
[77]
nes

Papaverine, laudanosine, sendaverine

Cularine
[78]
group

Cularine, yagonine

Pavines a
nd
isopavine
[79]
s

Argemonine, amurensine

Benzopyr
[
rocolines

Cryptaustoline

[78]

[79]

[71]

80]

Protoberb
[71]
erines

Berberine, canadine, ophiocarpine,

[81]
mecambridine, corydaline

Phthalidis
oquinolin
[71]
es

Hydrastine, narcotine (Noscapine)

Spirobenz
ylisoquino
[71]
lines

Fumaricine

Ipecacua
nha alkal
[83]
oids

Emetine, protoemetine, ipecoside

[82]

[79]

[83]

Benzophe
nanthridin
[71]
es

Sanguinarine, oxynitidine,
[84]
corynoloxine

Aporphin
[71]
es

Glaucine, coridine, liriodenine

Proaporp
[71]
hines

Pronuciferine, glaziovine

Homoapo
[86
rphines

[85]

[71][80]

Kreysiginine, multifloramine

[86]

Homopro
aporphine
[86]
s

Bulbocodine

Morphine
[87]
s

Morphine, codeine, thebaine, sinomen

[88]
ine

Homomor
[89]
phines

Kreysiginine, androcymbine

Tropolois
oquinolin
[71]
es

Imerubrine

Azofluora
[7
nthenes

[78]

[87]

[71]

Rufescine, imeluteine

[90]

1]

Amaryllis
[9
alkaloids
1]

Lycorine, ambelline,
[92]
tazettine, galantamine, montanine

Erythrina
[7
alkaloids

Erysodine, erythroidine

[75]

5]

Phenanth
rene deriv
[71]
atives

Atherosperminine

Protopins

[71][81]

[71]

Protopine, oxomuramine,
[84]
corycavidine

Aristolact
[71]
am

Doriflavin

[71]

Oxazole
derivative
[93]
s
Tyrosine tyramine

[94]

Annuloline, halfordinol, texaline,

[95]
texamine

Isoxazole
derivativ
es
Ibotenic acid Muscimol

Thiazole
derivative
[96]
s

Ibotenic acid, Muscimol

1-Deoxy-D-xylulose 5[9
[96][98]
phosphate (DOXP), tyrosine, cysteine Nostocyclamide, thiostreptone
7]

3,4Dihydro4quinazolo
ne
derivative
s

Febrifugine

Quinazoli 1,4nederivati Dihydro[99]

ves
4Anthranilic
quinazolo
[100]
acid or phenylalanine or ornithine
ne
derivative
s

Pyrrolidin
e and
piperidine
quinazolin
e
derivative
s

Acridine
derivative
[93]
s

[101]

Glycorine, arborine, glycosminine

Vazicine (peganine)

Anthranilic acid

[102]

Simple
Quinoline derivative
Anthranilic acid 3derivative s of
[107]
carboxyquinoline
[105][106]
quinoline
s
derivative
s of 2

[93]

Rutacridone, acronicine

[103][104]

Cusparine, echinopsine,
[106][108][109]
evocarpine

[101]

quinolon
esand 4quinolone

Tricyclic
terpenoid
s

Flindersine

Furanoqui
noline
derivative
s

Dictamnine, fagarine,
[106][111][112]
skimmianine

Quinines

[106][110]

Tryptophan tryptamine strictosidin

Quinine, quinidine, cinchonine,
e (with secologanin) korinanteal
[110]
cinhonidine
[73][107]
cinhoninon

Non-isoprene indole alkaloids

Simple
indole
Indole de derivative
[113]
[8
rivatives s

Serotonin, psilocybin, dimethyltryptami

[115][116]
ne (DMT),bufotenin

8]

Simple
derivative
Tryptophan tryptamine or 5s of [114]
[ hydroxitriptofan
carboline

Harman, harmine, harmaline,

[113]
eleagnine

117]

See
also: indo
le
Pyrroloind
alkaloids ole
[
alkaloids

Physostigmine (eserine), etheramine,

[118]
physovenine, eptastigmine

118]

Semiterpenoid indole alkaloids

Ergot
Tryptophan chanoclavine
[8
[119]
alkaloids agroclavine elimoclavine paspalic Ergotamine, ergobasine, ergosine
8]
[118]
acid lysergic acid

Monoterpenoid indole alkaloids

Ajmalicine, sarpagine,
vobasine, ajmaline, yohimbine,reserpi
[120][121]
ne, mitragynine,
group strychnin
e and (Strychnine brucine,
[122]
aquamicine, vomicine
)

Corynant
he type
[1
alkaloids
14]

IbogaTryptophan tryptamine strictosidin

type
[114]
[114]
Ibogamine, ibogaine, voacangine
[1 e (with secologanin)
alkaloids
14]

Aspidosp
erma-type
[1
alkaloids

Vincamine, vinca alkaloids, vincotine,

[123][124]
aspidospermine

14]

Imidazole
derivative
[93]
s
Directly from histidine

Purine de
[1
rivatives
26]

[125]

Histamine, pilocarpine, pilosine,

[93][125]
stevensine

Xanthosine (formed in purine

biosynthesis) 7 methylxantosine
Caffeine, theobromine, theophylline, s
7[127][128]
axitoxin
methylxanthine theobromine caffe
[73]
ine

Alkaloids with nitrogen in the side chain (protoalkaloids)

Phenylet
hylamine
derivative
[80]
s

Tyrosine or phenylalanine dioxyphen

ilalanine dopamine adrenaline an
dmescaline tyrosine tyramine phenyl
alanine 1-phenylpropane-1,2-dione
cathinone ephedrine and pseudoe
[12][40][129]
phedrine

Tyramine, ephedrine, pseudoephedrin

e, mescaline,cathinone, catecholamin
es (adrenaline, noradrenaline,dopamin
[12][130]
e)

Colchicin
e alkaloid
[131]
s
Tyrosine or phenylalanine dopamine
[131]
Colchicine, colchamine
[132]
autumnaline colchicine

Muscarin
[133]
e
Glutamic acid 3-ketoglutamic acid Muscarine, allomuscarine,
[134]
[133]
muscarine (with pyruvic acid)
epimuscarine, epiallomuscarine

Benzyla
[135]
mine

Phenylalanine with valine, leucine or is Capsaicin, dihydrocapsaicin,

[136]
[135][137]
oleucine
nordihydrocapsaicin

Polyamines alkaloids

Putrescin
ederivativ

ornithine putrescine spermidine

Paucine

[138]

es

[138]

spermine

[139]

Spermidi
nederivati
[138]
ves

Lunarine, codonocarpine

Spermine
derivative
[138]
s

Verbascenine, aphelandrine

[138]

[138]

Peptide (cyclopeptide) alkaloids

Peptide
alkaloids
with a 13membere
d
[36][14
cycle
0]

Nummula
rine C
type

Nummularine C, Nummularine S

Ziziphine
type

Ziziphine A, sativanine H

Frangulan
ine type

Frangulanine, scutianine J
From different amino acids

Peptide
Scutianin
alkaloids
e A type
with a 14membere
d
[36][14 Integerrin
cycle
e type
0]

Amphibin
e F type

[36]

[140]

[36]

Scutianine A

[36]

Integerrine, discarine D

[140]

Amphibine F, spinanine A

[36]

[36]

Amfibine
B type

Amphibine B, lotusine C

Peptide
alkaloids
with a 15- Mucronin
membere e A type
d
[140]
cycle

Mucronine A

[36]

[33][140]

Pseudoalkaloids (terpenes and steroids)

Diterpene
[33]
s

Steroids

Mevalonic
Lycoctoni
[33][143]
acid izopentenilpyrophosfate gera Aconitine, delphinine
ne type
[141][142]
nyl pyrophosphate

[1

44]
[145]

Cholesterol, arginine

Properties[edit]

Solasodine, solanidine,
[146]
veralkamine, batrachotoxin

Head of a lamb born by a sheep that ate leaves of the corn lily plant. The cyclopia in the calf is induced by the
alkaloidcyclopamine present in the plant.

Most alkaloids contain oxygen in their molecular structure; those compounds are usually colorless
[147]
[23]
crystals at ambient conditions. Oxygen-free alkaloids, such as nicotine
or coniine, are typically
[148]
volatile, colorless, oily liquids.
Some alkaloids are colored, like berberine (yellow)
[148]
andsanguinarine (orange).
Most alkaloids are weak bases, but some, such as theobromine and theophylline,
[149]
are amphoteric.
Many alkaloids dissolve poorly in water but readily dissolve in organic solvents,
such as diethyl ether, chloroform or 1,2[150]
[151]
[152]
[153]
dichloroethane. Caffeine,
cocaine,
codeine
and nicotine are water soluble (with a
[154]
[155]
solubility of 1g/L), whereas others, including morphine
and yohimbine
are highly water soluble
(0.11 g/L). Alkaloids and acids form salts of various strengths. These salts are usually soluble in
water and alcohol and poorly soluble in most organic solvents. Exceptions
include scopolamine hydrobromide, which is soluble in organic solvents, and the water-soluble
[148]
quinine sulfate.
Most alkaloids have a bitter taste or are poisonous when ingested. Alkaloid production in plants
appeared to have evolved in response to feeding by herbivorous animals; however, some animals
[156]
have evolved the ability to detoxify alkaloids.
Some alkaloids can produce developmental defects
in the offspring of animals that consume but cannot detoxify the alkaloids. One example is the
alkaloid cyclopamine, produced in the leaves of corn lily. During the 1950s, up to 25% of lambs born
by sheep that had grazed on corn lily had serious facial deformations. These ranged from deformed
jaws tocyclopia (see picture). After decades of research, in the 1980s, the compound responsible for
[157]
these deformities was identified as the alkaloid 11-deoxyjervine, later renamed to cyclopamine.

Distribution in nature[edit]

Strychnine tree. Its seeds are rich instrychnine and brucine.

Alkaloids are generated by various living organisms, especially by higher plants about 10 to 25% of
[158][159]
those contain alkaloids.
Therefore, in the past the term "alkaloid" was associated with
[160]
plants.
The alkaloids content in plants is usually within a few percent and is inhomogeneous over the plant
tissues. Depending on the type of plants, the maximum concentration is observed in the leaves (black
henbane), fruits or seeds (Strychnine tree), root (Rauwolfia serpentina) or bark
[161]
[162]
(cinchona). Furthermore, different tissues of the same plants may contain different alkaloids.
Beside plants, alkaloids are found in certain types of fungi, such as psilocybin in the fungus of the
[15]
genus Psilocybe, and in animals, such as bufoteninin the skin of some toads. Many marine
[163]
organisms also contain alkaloids.
Some amines, such as adrenaline and serotonin, which play an
important role in higher animals, are similar to alkaloids in their structure and biosynthesis and are
[164]
sometimes called alkaloids.

Extraction[edit]

Crystals of piperine extracted from black pepper.

Because of the structural diversity of alkaloids, there is no single method of their extraction from
[165]
natural raw materials.
Most methods exploit the property of most alkaloids to be soluble in organic
solvents but not in water, and the opposite tendency of their salts.
Most plants contain several alkaloids. Their mixture is extracted first and then individual alkaloids are
[166]
[165][167]
separated.
Plants are thoroughly ground before extraction.
Most alkaloids are present in the
[165]
raw plants in the form of salts of organic acids.
The extracted alkaloids may remain salts or
[166]
change into bases.
Base extraction is achieved by processing the raw material with alkaline
solutions and extracting the alkaloid bases with organic solvents, such as 1,2-dichloroethane,
chloroform, diethyl ether or benzene. Then, the impurities are dissolved by weak acids; this converts
alkaloid bases into salts that are washed away with water. If necessary, an aqueous solution of
alkaloid salts is again made alkaline and treated with an organic solvent. The process is repeated until
the desired purity is achieved.
In the acidic extraction, the raw plant material is processed by a weak acidic solution (e.g., acetic
acid in water, ethanol, or methanol). A base is then added to convert alkaloids to basic forms that are
extracted with organic solvent (if the extraction was performed with alcohol, it is removed first, and the
[165][168]
remainder is dissolved in water). The solution is purified as described above.
Alkaloids are separated from their mixture using their different solubility in certain solvents and
[169]
different reactivity with certain reagents or bydistillation.

Biosynthesis[edit]

Biological precursors of most alkaloids are amino acids, such

as ornithine, lysine, phenylalanine, tyrosine, tryptophan, histidine, aspartic acid, andanthranilic
[170]
acid.
Nicotinic acid can be synthesized from tryptophan or aspartic acid. Ways of alkaloid
[73]
biosynthesis are too numerous and cannot be easily classified. However, there are a few typical
reactions involved in the biosynthesis of various classes of alkaloids, including synthesis ofSchiff
[170]
bases and Mannich reaction.

Synthesis of Schiff bases[edit]

Main article: Schiff base
Schiff bases can be obtained by reacting amines with ketones or aldehydes.
[172]
common method of producing C=N bonds.

[171]

These reactions are a

In the biosynthesis of alkaloids, such reactions may take place within a molecule,
[29]
synthesis of piperidine:

[170]

such as in the

Mannich reaction[edit]
Main article: Mannich reaction
An integral component of the Mannich reaction, in addition to an amine and a carbonyl compound, is
a carbanion, which plays the role of the nucleophile in the nucleophilic addition to the ion formed by
[172]
the reaction of the amine and the carbonyl.

The Mannich reaction can proceed both intermolecularly and intramolecularly:

[173][174]

Dimer alkaloids[edit]
In addition to the described above monomeric alkaloids, there are also dimeric, and
even trimeric and tetrameric alkaloids formed upon condensation of two, three, and four monomeric
alkaloids. Dimeric alkaloids are usually formed from monomers of the same type through the following
[175]
mechanisms:

Mannich reaction, resulting in, e.g., voacamine

Michael reaction (villalstonine)

Condensation of aldehydes with amines (toxiferine)

Oxidative addition of phenols (dauricine, tubocurarine)

Lactonization (carpaine).

Voacamine

Villalstonine

Toxiferine

Dauricine

Tubocurarine

Carpaine

The biological role[edit]

[176]

The role of alkaloids for living organisms that produce them is still unclear.
It was initially assumed
that the alkaloids are the final products of nitrogen metabolism in plants, as urea in mammals. It was
[8]
later shown that alkaloid concentrations varies over time, and this hypothesis was refuted.
Most of the known functions of alkaloids are related to protection. For
example, aporphine alkaloid liriodenine produced by the tulip tree protects it from parasitic
mushrooms. In addition, presence of alkaloids in the plant prevents insects and chordate animals
from eating it. However, some animals adapted to alkaloids and even use them in their own
[177]
metabolism.
Such alkaloid-related substances as serotonin, dopamine and histamine are
[178]
important neurotransmitters in animals. Alkaloids are also known to regulate plant growth.
Another
example of an organism that uses alkaloids for protection is the Utetheisa ornatrix, more commonly
known as the Ornate Moth. Pyrrolizidine alkaloids render these larvae and adult moths unpalatable to
many of their natural enemies like coccinelid beetles, green lacewings, insectivorous hemiptera and
[179]
insectivorous bats.

Applications[edit]
In medicine[edit]
Medical use of alkaloid-containing plants has a long history, and, thus, when the first alkaloids were
[180]
isolated in the 19th century, they immediately found application in clinical practice.
Many alkaloids
[8][181]
are still used in medicine, usually in the form of salts, including the following:

Alkaloid

Ajmaline

Action

antiarrhythmic

Atropine, scopolamine, hyoscyamine anticholinergic

Caffeine

Stimulant, diuretic, Adenosine receptor antagonist

Codeine

cough medicine, analgesic

Colchicine

remedy for gout

Emetine

antiprotozoal agent

Ergot alkaloids

sympathomimetic, vasodilator, antihypertensive

Morphine

analgesic

Nicotine

Stimulant, Nicotinic acetylcholine receptor agonist

Physostigmine

inhibitor of acetylcholinesterase

Quinidine

antiarrhythmic

Quinine

antipyretics, antimalarial

Reserpine

antihypertensive

Tubocurarine

Muscle relaxant

Vinblastine, vincristine

antitumor

Vincamine

vasodilating, antihypertensive

Yohimbine

Stimulant, Aphrodisiac

Many synthetic and semisynthetic drugs are structural modifications of the alkaloids, which were
designed to enhance or change the primary effect of the drug and reduce unwanted side[182]
effects.
For example, naloxone, an opioid receptor antagonist, is a derivative of thebaine that is
[183]
present in opium.

Thebaine

Naloxone

In agriculture[edit]
Prior to the development of a wide range of relatively low-toxic synthetic pesticides, some alkaloids,
such as salts of nicotine and anabasine, were used as insecticides. Their use was limited by their high
[184]
toxicity to humans.

Use as psychoactive drugs[edit]

Preparations of plants containing alkaloids and their extracts, and later pure alkaloids, have long been
used as psychoactive substances. Cocaine and cathinone are stimulants of the central nervous
[185][186]
system.
Mescaline and many of indole alkaloids (such
as psilocybin, dimethyltryptamine and ibogaine)
[187][188]
[189]
have hallucinogenic effect.
Morphine and codeine are strong narcotic pain killers.
There are alkaloids that do not have strong psychoactive effect themselves, but are precursors for
semi-synthetic psychoactive drugs. For example, ephedrine and pseudoephedrine are used to
[190]
produce methcathinone and methamphetamine.
Thebaine is used in the synthesis of many
painkillers such as oxycodone.

See also[edit]

Amine

Base (chemistry)

Natural products

Palau'amine

Secondary metabolite

Mayer's reagent

Notes[edit]
1.

Jump up^ In the penultimate sentence of his article W. Meissner (1819) "ber Pflanzenalkalien: II.
ber ein neues Pflanzenalkali (Alkaloid)" (On plant alkalis: II. On a new plant alkali (alkaloid)), Journal
fr Chemie und Physik, 25 : 379381 ; available on-line at: Hathi Trust Meissner wrote: "berhaupt
scheint es mir auch angemessen, die bis jetzt bekannten Pflanzenstoffe nicht mit dem Namen Alkalien,
sondern Alkaloide zu belegen, da sie doch in manchen Eigenschaften von den Alkalien sehr
abweichen, sie wrden daher in dem Abschnitt der Pflanzenchemie vor den Pflanzensuren ihre Stelle
finden." (In general, it seems appropriate to me to impose on the currently known plant substances not
the name "alkalis" but "alkaloids", since they differ greatly in some properties from the alkalis; among
the chapters of plant chemistry, they would therefore find their place before plant acids [since "Alkaloid"
would precede "Sure" (acid)].)

An alkaloid is a naturally occurring nitrogenous organic molecule that has a pharmacological effect
on humans and other animals. The name derives from the word alkaline; originally, the term was used
to describe any nitrogen-containing base (an amine in modern terms). Alkaloids are found
in plants (e.g., in potatoes and tomatoes), animals (e.g., in shellfish) and fungi (e.g., inmushrooms),
and can be extracted from their sources by treatment with acids (usually hydrochloric acid or sulfuric
acid, though organic acids such as maleic acid and citric acid are sometimes used).
The main article for this category is Alkaloid.

alkaloid, any of a class of naturally occurring organic nitrogen-containing bases. Alkaloids have
diverse and important physiological effects on humans and other animals. Well-known alkaloids
includemorphine, strychnine, quinine, ephedrine, and nicotine.
Alkaloids are found primarily in plants and are especially common in certain families of flowering
plants. More than 3,000 different types of alkaloids have been identified in a total of more than
4,000plant species. In general, a given species contains only a few kinds of alkaloids, though
both the opium poppy (Papaver somniferum) and the ergot fungus (Claviceps) each contain
about 30 different types. Certain plant families are particularly rich in alkaloids; all plants of
the poppy family (Papaveraceae) are thought to contain them, for example. The Ranunculaceae
(buttercups), Solanaceae (nightshades), and Amaryllidaceae (amaryllis) are other prominent
alkaloid-containing families. A few alkaloids have been found in animal species, such as the New
World beaver (Castor canadensis) and poison-dart frogs (Phyllobates). Ergot and a few other
fungi also produce them.
The function of alkaloids in plants is not yet understood. It has been suggested that they are
simply waste products of plants metabolic processes, but evidence suggests that they may
serve specific biological functions. In some plants, the concentration of alkaloids increases just
prior to seed formation and then drops off when the seed is ripe, suggesting that alkaloids may
play a role in this process. Alkaloids may also protect some plants from destruction by certain
insect species.
The chemical structures of alkaloids are extremely variable. Generally, an alkaloid contains at
least one nitrogen atom in an amine-type structurei.e., one derived from ammonia by replacing
hydrogen atoms with hydrogen-carbon groups called hydrocarbons. This or another nitrogen
atom can be active as a base in acid-base reactions. The name alkaloid (alkali-like) was
originally applied to the substances because, like the inorganic alkalis, they react with acids to
form salts. Most alkaloids have one or more of their nitrogen atoms as part of a ring of atoms,
frequently called a cyclic system. Alkaloid names generally end in the suffix -ine, a reference to
their chemical classification as amines. In their pure form most alkaloids are colourless,
nonvolatile, crystalline solids. They also tend to have a bitter taste.
Interest in the alkaloids stems from the wide variety of physiological effects (both wanted and
unwanted) they produce in humans and other animals. Their use dates back to ancient
civilizations, but scientific study of the chemicals had to await the growth of organic chemistry, for
not until simple organic bases were understood could the intricate structure of the alkaloids be
unraveled. The first alkaloid to be isolated and crystallized was the potent active constituent of
the opium poppy, morphine, in about 1804.
Alkaloids are often classified on the basis of their chemical structure. For example, those
alkaloids that contain a ring system called indole are known as indole alkaloids. On this basis,
the principal classes of alkaloids are the pyrrolidines, pyridines, tropanes, pyrrolizidines,
isoquinolines, indoles, quinolines, and the terpenoids and steroids. Alternatively, alkaloids can be
classified according to the biological system in which they occur. For example, the opium
alkaloids occur in the opium poppy (Papaver somniferum). This dual classification system

actually produces little confusion because there is a rough correlation between the chemical
types of alkaloids and their biological distribution.
The medicinal properties of alkaloids are quite diverse. Morphine is a powerful narcotic used for
the relief of pain, though its addictive properties limit its usefulness. Codeine, the methyl ether
derivative of morphine found in the opium poppy, is an excellent analgesic that is relatively
nonaddictive. Certain alkaloids act as cardiac or respiratory stimulants. Quinidine, which is
obtained from plants of the genusCinchona, is used to treat arrhythmias, or irregular rhythms of
the heartbeat. Many alkaloids affect respiration, but in a complicated manner such that severe
respiratory depression may follow stimulation. The drug lobeline (from Lobelia inflata) is safer in
this respect and is therefore clinically useful. Ergonovine (from the fungus Claviceps purpurea)
and ephedrine (from Ephedra species) act as blood-vessel constrictors. Ergonovine is used to
reduce uterine hemorrhage after childbirth, and ephedrine is used to relieve the discomfort of
common colds, sinusitis, hay fever, and bronchial asthma.
Many alkaloids possess local anesthetic properties, though clinically they are seldom used for
this purpose. Cocaine (from Erythroxylon coca) is a very potent local
anesthetic. Quinine (from Cinchonaspecies) is a powerful antimalarial agent that was formerly
the drug of choice for treating that disease, though it has been largely replaced by less toxic and
more effective synthetic drugs. The alkaloidtubocurarine is the active ingredient in the South
American arrow poison, curare (obtained fromChondrodendron tomentosum), and is used as a
muscle relaxant in surgery. Two alkaloids, vincristine andvinblastine (from Vinca rosea), are
widely used as chemotherapeutic agents in the treatment of many types of cancer.
Nicotine obtained from the tobacco plant (Nicotiana tabacum) is the principal alkaloid and chief
addictive ingredient of the tobacco smoked in cigarettes, cigars, and pipes. Some alkaloids are
illicit drugs and poisons. These include the hallucinogenic
drugs mescaline (from Anhalonium species) andpsilocybin (from Psilocybe mexicana). Synthetic
derivatives of the alkaloids morphine and lysergic acid(from C. purpurea)
produce heroin and LSD, respectively. The alkaloid coniine is the active component of the
poison hemlock (Conium maculatum). Strychnine (from Strychnos species) is another powerful
poison.
Special methods have been developed for isolating commercially useful alkaloids. In most cases,
plant tissue is processed to obtain aqueous solutions of the alkaloids. The alkaloids are then
recovered from the solution by a process called extraction, which involves dissolving some
components of the mixture with reagents. Different alkaloids must then be separated and purified
from the mixture.Chromatography may be used to take advantage of the different degrees of
adsorption of the various alkaloids on solid material such as alumina or silica. Alkaloids in
crystalline form may be obtained using certain solvents.

Volume 7 (Number 3) Fall 1998

Plants That Make You Loco

Mind-Altering Plant Alkaloids

Introduction, Disclaimer And Warnings

Trees Protected By Ants Instead Of Alkaloids
The Deadly Datura Called Jimsonweed
A Junkie Moth That Pollinates Jimsonweeds
Old & New World Hallucinogenic Mushrooms
Ergot: A Grain Fungus That Contains LSD
A Hallucinogen In Seeds & The Skin Of Toads
LSD-Producing Morning Glories From Mexico
Locoweeds: Wild And Crazy Plants
The Mescal Bean and Peyote Cactus
Ephedrine Alkaloids From Ephedra
Photos Of Alkaloid-Producing Plants
References About Plant Alkaloids

Introduction, Disclaimer & Warnings:

This WAYNE'S WORD is dedicated to those mind-altering plants that have been
used (and sometimes abused) by people, but have also provided us with some
valuable medicinal drugs. For countless generations they have given native people
throughout the world a spiritual means of communicating with their gods and
deceased loved ones.
The article will discuss plants containing different types of mind-altering alkaloids.
It will contain photos of some of the plants, illustrations of their potent alkaloids,
simplified explanations of the mechanisms of these poisons, and anecdotal tidbits
not usually found in this type of subject matter.
DISCLAIMER: Some of the plants discussed in this article contain very poisonous
alkaloids which can be lethal if ingested in sufficient quantities. Native people
developed time-tested religious rituals using these plants that were passed down
through countless generations.

This article is mostly about the adaptive advantage of alkaloids in plants, and some
remarkable examples of psychoactive (hallucinogenic) alkaloids found in some of the most
amazing plants on earth. Stimulant (or tranquilizer) alkaloids such as nicotine from tobacco

(Nicotiana tabacum), caffeine from coffee (Coffea arabica), and cocaine from coca
(Erythroxylum coca) are highly addictive and clearly alter one's mental and physical state, but
are beyond the scope of this article. Likewise, narcotic, pain-relieving alkaloids from the
opium poppy (Papaver somniferum), including codeine and morphine, are excluded from this
article. Although marijuana (Cannabis sativa) is often discussed in books about mind-altering
plants, its active chemical tetrahydrocannabinol (THC) is not an alkaloid. It does not contain
nitrogen and consists of both terpene and phenolic subunits--hence, it is called a
terpenophenolic compound. For those interested in further reading, the references at the
end of this article are a good place to start.

uring the past 130 million years, flowering plants have colonized practically
every habitat on earth, from arid deserts, boggy meadows and windswept alpine
summits, to sun-baked grasslands, lush rain forests and wave-battered rocky
shores. They have replaced most of the ancient ferns and seed plants that dinosaurs
subsisted on, and developed a complex and fascinating relationship with insects
and mammals. During these countless centuries of time, flowering plants have
gradually evolved all sorts of ingenious protective devices to discourage hungry
herbivorous animals. Leaves and stems have developed a variety of vicious spines
and stinging hairs (trichomes). In some plants, the dense covering of silvery hairs
may also provide other ecological advantages such as solar reflection and
insulation in arid environments. But mechanical defenses, such as spines and
trichomes, are of limited value and probably would not deter all hungry herbivores,
particularly the chewing and sucking insects. Therefore, plants have developed a
"chemical warfare," a defense strategy based on a vast arsenal of chemicals which
are toxic or distasteful to animals. According to Daniel Janzen, noted authority of
the Costa Rican rain forest, developing seeds of the tropical
liana Mucuna (including M. urens and M. pruriens) are nearly free from seed
predators. [These vines produce the distinctive hamburger-shaped "sea beans" that
drift ashore on tropical beaches throughout the world.] In addition to a dense
covering of stinging trichomes, the pods of Mucuna are rich in the potentially
toxic amino acid L-dopa. [L-dopa, precursor of the brain neurotransmitter
dopamine, is given to patients suffering from Parkinson's Disease.] Just as genetic
variability and time allow agricultural pests to tolerate pesticides, so can some
herbivores circumvent a plant's natural chemical defenses. This "predatory
pressure" has resulted in the evolution of an endless array of complex plant
molecules, from gums and terpenes to alkaloids and phenolic compounds. For
example, in nettles (Urtica species) the sophisticated defense chemicals
acetylcholine and histamine are employed in an ingenious system of "injection
hairs" strategically placed throughout the plant. When we touch these plants, we

may be accidental casualties in a chemical warfare between plants and herbivores

that has waged through countless millennia.

ne of the largest groups of chemical arsenals produced by plants are the

alkaloids. Many of these metabolic by-products are derived from amino acids and
include an enormous number of bitter, nitrogenous compounds. According to R.F.
Raffauf (Plant Alkaloids: A Guide To Their Discovery and Distribution, 1996),
more than 10,000 different alkaloids have been discovered in species from over
300 plant families. Alkaloids often contain one or more rings of carbon atoms,
usually with a nitrogen atom in the ring. The position of the nitrogen atom in the
carbon ring varies with different alkaloids and with different plant families. In
some alkaloids, such as mescaline, the nitrogen atom is not within a carbon ring. In
fact, it is the precise position of the nitrogen atom that effects the properties of
these alkaloids. Although they undoubtedly existed long before humans, some
alkaloids have remarkable structural similarities with neurotransmitters in the
central nervous system of humans, including dopamine, serotonin and
acetylcholine. The amazing effect of these alkaloids on humans has led to the
development of powerful pain-killer medications, spiritual drugs, and serious
addictions by people who are ignorant of the properties of these powerful
chemicals.

A Tree Protected By Ants Instead Of Alkaloids

housands of different alkaloids have been discovered from throughout the plant
kingdom, but there are some species that do not contain any of these bitter,
nitrogenous compounds. One of the most remarkable examples of the "competitive
disadvantage" of a tree unable to produce alkaloids is the bullhorn acacia (Acacia
cornigera) of Central America. The common name of "bullhorn" refers to the
large, swollen thorns (technically called stipular spines) that occur in pairs at the
base of leaves, and superficially resemble the horns of a steer. In fact, the thorns
of A. cornigera, and a related species A. collinsii, are so striking that they are
often strung into unusual necklaces and belts. In El Salvador the horn-shaped
thorns provide the legs for small ballerina seed dolls which are worn as decorative
pins.

ccording to the famous botanist G.L. Stebbins (Flowering Plants: Evolution

Above The Species Level, 1974), other species ofAcacia growing in the same
region of Central America (including A. chiapensis and A. macrantha) produce

alkaloids, but grow much more slowly and live in drier areas than A. cornigera.
Apparently these other species of Acacia pay the price for their alkaloid defense
system in terms of a slower growth rate, which enables them to compete only in
the drier regions where the growth of competing vegetation is also slower and less
vigorous. The ability of A. cornigera to enter more moist, lush vegetation areas is
apparently related to its evolution of another defense system that depends on a little
hymenopteran helpmate rather than the production of bitter alkaloids.

he "swollen-thorn" acacias of Central America are truly remarkable trees. In

the wild, their enlarged, hollowed-out stipular spines are occupied by fiercely
biting-stinging ants that protect them from browsing herbivores and epiphytic
plants that might shade them out. The swollen thorns are not galls, they are not
produced in response to chemical or physical stimuli from invasive insects
imbedded in their tissues. The amazing thorns are genetically-programmed
structures that are formed with or without the presence of symbiotic ants. On wild
trees they are inhabited by colonies of Pseudomyrmex ferruginea, very
aggressive ants with a painful sting. Disturbed ants release an alarm pheromone
and rush out of their thorn "barracks" in great numbers. According to Daniel
Janzen (Costa Rican Natural History, 1983), livestock can apparently smell the
pheromone and avoid these acacias day and night. Getting stung in the mouth and
tongue is an effective deterrent to browsing on the tender foliage. In addition to
protecting A. collinsii from leaf-cutting ants and other unwanted herbivores, the
ants also clear away invasive seedlings around the base of the tree that might
overgrow it and block out vital sunlight. According to Daniel Janzen (Smithsonian
Contributions to Botany Number 13, 1974), the Central American swollen-thorn
acacias lack the chemical defenses of most other acacias to discourage ravaging
insect predators and competition, and symbiotic ants have taken over this vital role.
The acacias reward their ant helpmates with thorn "condos" to live in,
carbohydrate-rich nectar from glands on the leaf stalks, and nourishing, proteinlipid morsels called Beltian bodies on the leaflet tips. There is no known function
for Beltian bodies, except to provide food for symbiotic ants.

rior to settling on a thorn acacia, the winged virgin queen ant goes on a mating
flight to the highest treetop or nearby hill. Here she gets inseminated by a winged
male and then hunts for an acacia in which to lay her eggs. [This "hilltopping"
phenomenon also occurs in San Diego County, California, where sexually mature
adult male and female butterflies fly upslope to a rendezvous point at the summit!]
The queen ant cuts an entrance hole into a green thorn, hollows it out, and then
deposits her eggs. Subsequent entrance holes are cut by the new generations of
worker ants. All this astonishing, complicated behavior has evolved in a tree that
for some reason doesn't synthesize alkaloids.

An Acacia Protected By Ants Instead Of Alkaloids

hile peppers in the wild may also benefit from a naturally-occurring alkaloid
present in their fruits. The active ingredient causing the intense burning pain when
you chew into the walls of these fruits, especially the placental region where the
seeds are attached, is the alkaloid capsaicin. So potent is this alkaloid that one
millionth of a drop can be detected by the human tongue. Capsaicin is not broken
down during the digestion process--this is why you often get burned several hours
later after dining on chile peppers. Like other alkaloids in the chemical arsenal of
plants, capsaicin may serve to discourage mammalian fruit predators. Botanists
believe that birds are immune to the burning sensation of capsaicin, and may serve
to disperse the seeds. Capsaicin may prevent hungry mammals from devouring the
fruits, so that they can be eaten by fruit-eating birds who are attracted to bright red
fruits. Passing through the bird's digestive tract relatively unharmed, the small
seeds are dispersed to other favorable regions. According to D. Dewitt and P. W.
Bosland (Peppers of the World: An Identification Guide, Ten Speed Press,
Berkeley, California, 1996), there are 5 species of Capsicum peppers native to the
New World: C. pubescens, C. baccatum, C. annuum, C. frutescens and C.
chinense. The hottest chile peppers belong the C. chinensegroup, including the
notorious habanero. Although this species is named "chinense," it is not from
China. Actually, its center of origin is thought to be the Amazon Basin of South
America.
See Article About Hot Chile Peppers

The Deadly Datura

here are approximately 25 different species of Datura throughout the world,

including Europe, Africa, southeast Asia, Central and South America, Mexico and
the United States. They are often called jimsonweed or "thornapple." The latter
name refers to the spiny seed-bearing capsules. Most of the species are low,
shrubby or sprawling annuals or perennials, but some tree-like forms may reach 11
meters (36 feet) in height. The tree-like forms are occasionally cultivated as
ornamentals and are usually placed in the genus Brugmansia. They generally have
the same characteristic trumpet-shaped flowers as Datura with striking color
variations of red, pink and yellow. Both genera belong to the Nightshade Family
(Solanaceae), along with the deadly nightshade (Solanum dulcamara) , tomato

(Lycopersicum esculentum), eggplant (Solanum melongena) and potato (S.

tuberosum). Many species of Solanum (called nightshades) are quite poisonous to
humans if eaten raw. Incidentally, the new sprouts of potato tubers contain the
toxic alkaloids solanine and solanidine. Until about a century ago the tomato was
thought to be poisonous because of its toxic relatives.

he common native Datura of the western United States, with rank-smelling

foliage and large, white flowers up to 20 centimeters (8 inches) long is D. wrightii.
Sometimes the flowers are tinged with purple and resemble oversized petunia or
morning glory blossoms. It is a sprawling perennial with an enormous taproot that
may extend more than 60 centimeters (2 feet) into the ground. D. wrightii has a
large geographic range, including California, Utah, Arizona, New Mexico and
Texas. It is often listed in older references as D. meteloides, a name that actually
applies to a similar Mexican species, D. inoxia ssp. inoxia. Another species with
smaller flowers, D. discolor, is native to desert washes and riverbeds of
southeastern California and Arizona.

The large, trumpet-shaped flowers of jimsonweed (Datura wrightii) are

sometimes tinged with purple and resemble giant morning glory

blossoms. It actually belongs to the tomato family (Solanaceae) along

with petunias, potatoes and tomatoes. This remarkable plant is common
along roadsides and riverbeds throughout the western United States, and
is one of the largest and most striking of all native wildflowers.

third species, Datura stramonium, is naturalized throughout the United

States. Most older references list D. stramonium as an Old World species
naturalized as an weed in North America. According to Dr. Robert Bye of the
Universidad Nacional Autonoma de Mexico (personal communication, 1987), D.
stramonium probably originated in the New World and migrated to the Old World
during pre-Columbian time. It can readily be distinguished from D. wrightii by its
more erect habit, smaller flowers and distinctive angular or prismatic calyx. It is a
cosmopolitan annual weed and prolific seed-producer. A dozen viable seeds
planted in fertile soil in spring may give rise to nearly 50,000 seeds by late
summer, an increase of more than 400,000 percent.

lthough jimsonweed is synonymous with several species of Datura, this

unusual common name is actually derived from D. stramonium. In 1676 British
soldiers stationed in Jamestown, Virginia became intoxicated by D.
stramonium when it was inadvertently included in their salads by the regimental
cooks. The episode was widely publicized and the plant culprit became known as
"Jamestown weed", and later as jimsonweed.

he leaves, stem, root and fruits of Datura contain a battery of tropane

alkaloids, the most potent of which are atropine, hyoscyamine and scopolamine.
These alkaloids affect the central nervous system, including nerve cells of the brain
and spinal cord which control many direct body functions and the behavior of men
and women. They may also affect the autonomic nervous system, which includes
the regulation of internal organs, heartbeat, circulation and breathing. One
autonomic response of atropine is the dilation of pupils, once considered to be a
beautiful and mysterious look in Italian women. In fact, belladonna means
"beautiful lady," so named because sap from the closely related belladonna plant
(Atropa belladonna) was used as eye drops to dilate the pupils.

he action of tropane alkaloids at the cellular level is complex. It is summarized

by R.E. Schultes and A. Hofmann in the The Botany and Chemistry of

Hallucinogens (1973) and in Medical Botany by W.H. Lewis and M.P.F. ElvinLewis (1977). Tropane alkaloids are found in many other poisonous plants,
including henbane (Hyoscyamus niger), pituri (Duboisia spp.), and mandrake
(Mandragora officinarum), all of which were used extensively in witches' brews
and folk medicines.

common property of tropane

alkaloids is a methylated nitrogen

atom N-CH3 at one end of the molecule
(see illustration at left). This chemical
structure is also found in the
neurotransmitter acetylcholine, which
transmits impulses between nerves in
the brain and neuromuscular junctions.

he anesthetic properties of tropane alkaloids may relate to their interference

with acetylcholine, perhaps by competing with it at the synaptic junctions, thus
blocking or inhibiting nerve impulses. It is interesting to note that the infamous
tropane alkaloid, cocaine, is also a local anesthetic when injected into skin or
muscle tissue. This property led to the discovery and synthesis of the more potent
compound, novocain, widely used in dentistry.

ithout getting into complicated anatomy and physiology, one nerve cell
(neuron) connects to an adjacent neuron by a long extension called an axon. The
axon branches into axonal endings, each of which attaches to the adjacent neuron
at a synaptic knob filled with acetylcholine. The minute gap or synaptic cleft
within this knob is only about 0.02 micrometers. As a nerve impulse (wave of
depolarization or action potential) reaches this gap, acetylcholine diffuses across
the synaptic cleft and activates the adjacent neuron. Acetylcholine in the synaptic
cleft is deactivated or broken down by the enzyme acetylcholinesterase, thus
shutting off the action potential. Organophosphate insecticides, such as malathion
and parathion, bind to active sites on this enzyme, thus preventing the normal shut
down of nerve impulses and destroying the nervous control of insects. Nerve
gasses developed during World War II have a similar effect on the nervous system.

Gulf War soldiers carried an atropine syrette to counter the possible effects of
nerve gas.

epending on the dosages, several tropane alkaloids of Datura (when absorbed

together) may have synergistic properties resulting in extreme hallucinations,
delirium and death. Since the alkaloids are fat soluble they are readily absorbed
through the skin and mucous membranes. Volumes have been written about the
uses and properties of Datura in the Middle Ages. Most of the uses involved the
consumption of potions or concoctions made from various parts of the plant.

uring ancient religious rituals in India, seeds were eaten by priests to induce
hallucinogenic, prophetic and oracular states. European priests apparently
drank Datura for the same reason. Some authorities believe the intoxicating smoke
inhaled by Greek priests over 2,000 years ago at the Oracle of Delphi was Datura.
Thieves in India and Europe used Datura for centuries as "knockout drops" to rob
their stupefied victims. The plant was also known in China, where a law prohibited
mixing it with wine and other drinks.

n the East Indies, women fed Datura leaves to beetles, and then fed the
poisonous dung to faithless lovers. Prostitutes in India added the seeds to their
patron's drinks to induce sexual excitement. In fact, the use of Datura as an
aphrodisiac spread throughout India, the Far East and Europe, and was an
important ingredient in love potions and witches' brews. Specially prepared salves
and ointments were also applied to various parts of the body. The famous
seventeenth century Dutch artist, David Teniers the Younger, made several
paintings of witches preparing for their demonic orgy or sabbat. The scenes
frequently depicted a nude witch being anointed while she straddled a broom.
According to M.J. Harner, writing in Hallucinogens and Shamanism (1973), the
use of a broom or staff was undoubtedly more than a symbolic Freudian act, for it
served to apply the salves to sensitive vaginal membranes.

lay tablets from Babylonian and Assyrian ruins indicate that Datura was used
medically in ancient civilizations several thousand years ago. Greek and Roman
physicians used Datura mixed with opium as a sedative and general anesthetic
during surgery. In fact, the use of scopolamine (one of the alkaloids in Datura)
plus morphine as an effective pain reliever and sleep inducer was common practice
until the nineteenth century.

ne of the most interesting medical cases of the 20th century involved a

German physician, Dr. Carl Gauss, and the Lutheran Church. In 1905, Dr. Gauss
used extracts from Datura and morphine to induce twilight sleep treatment for
women experiencing difficult child birth. The church elders denounced Dr. Gauss
because the Old Testament said that women were to bring forth in pain
(Genesis 3:16). The combination of scopolamine (one of the active alkaloids found
in Datura) plus morphine was used for years as an effective pain reliever and sleep
inducer; however, it is generally considered unsatisfactory for women in labor
because of hallucinogenic side effects on the mother, and it may repress breathing
of the newborn.

atura had a number of uses among Indian tribes of the United States, as well
as Mexico and South America. In fact, it is difficult to find a tribe that didn't use a
species of Datura from their region in one way or another. The hallucinogenic
uses involved drinking an infusion made from the crushed roots or sometimes the
crushed seeds fermented in water. Some aboriginal Indians in South America gave
a Datura-alcohol beverage to wives and slaves of dead warriors and chieftains.
The powerful brew induced stupor before they were buried alive to accompany
their dead husbands and masters on the long journey to heaven. The high priests of
some tribes took Datura in order to communicate with spirits of the dead and with
their gods. The brilliant red-flowered tree Datura (Brugmansia sanguinea) is
used today by herbal healers called "curanderos" in several countries of South
America.

robably the best known use of Datura by several North American Indian tribes
was the puberty ceremonial dances involving the drinking of a "toloache" (Datura)
infusion by young boys preparing to enter manhood. The ceremonies generally
involved wild erratic dancing, varied hallucinations, and finally unconsciousness.

atura alkaloids even have modern medicinal uses. The fat solubility of
tropane alkaloids is employed in a remarkable remedy for seasick mariners called
Transderm Scop. A small, medicated disc resembling a circular Band-Aid
releases small amounts of scopolamine into the bloodstream for up to 3 days. The
anti-nausea effects of scopolamine may relate to its anticholinergic action on the
central nervous system, which results in inhibition of the vomiting reflex.

See Deadly Daturas In Full Bloom

The Jimsonweed Junkie Moth

he nocturnal blossoms and pollination ecology of Datura wrightii are among

the most ingenious and unusual of all wildflowers of western North America. The
entire corolla is neatly folded or pleated (plicate) and twisted (convolute) in the
bud forming a compact cylinder. Each day at dusk during the summer months the
buds begin to gradually unfold. Each corolla slowly unfurls and then suddenly
snaps open as the intertwined lobes come lose from one another. At this instant a
powerful fragrance is emitted.

ive long stamen filaments are attached to the funnelform corolla at the throat.
The filaments extend as ridges down the inner corolla tube, forming 5 narrow
canals to the base of the ovary where the disc-shaped nectary is located. The nectar
canals can best be seen by examining a corolla tube in cross section. The curious
name "revolver flower" refers to nectar canals which resemble the cylinder
chambers of a 5-shot revolver. At night the nectar oozes along the length of the
canals within the corolla tube.

uring mid and late summer the white, fragrant blossoms are frequently visited
by large nocturnal hawk moths (family Sphingidae). They are sometimes called
sphinx moths because the alarm posture of the larva resembles the Egyptian
sphinx. Several species of hawk moths are known to visit blossoms of Datura
wrightii, but two of the most common are Manduca quinquemaculata and M.
sexta. The larval forms of both are better known as tomato and tobacco
hornworms.

ince Datura, tomatoes and tobacco all belong to the Nightshade family
(Solanaceae), the larvae are apparently content to feed on whichever plant is
available to them. The larvae are remarkably camouflaged with green markings
and are difficult to spot as they rapidly devour your tomato plants. After feasting
on Datura (or your tomato plants) all summer, the robust, ravenous caterpillars
crawl to the ground and burrow into the soil where they undergo pupation. Unlike
many other moth larvae they do not spin a cocoon. Probably every tomato gardener

has unearthed the large, carmel-colored pupa with its peculiar "jug handle"
appendage, which is actually a case for the developing proboscis of the adult moth.

n warm regions there may be two generations per year: summer pupae produce
adults after only a week or two; fall pupae remain in the ground until the following
late spring or summer. The adult moth emerges from the pupal case and pushes out
of the soil, eventually flying off into the night. After mating the gravid (pregnant)
female lays her eggs on a convenient Datura plant--or on your prize-winning
tomato plants while you sleep.

dult moths have remarkable proboscides (tongues) up to 12 centimeters long

(over 4 inches), long enough to reach the base of a 10-11 centimeter (4 inch)
corolla tube. When the moth is not feeding the remarkable tongue rolls up into a
neat, compact coil. The common white-lined sphinx moth (Hyles lineata) of the
American southwest, with a medium proboscis of 3-5 centimeters (2 inches), can
only reach nectar in the upper part of the nectar canals. Unlike
the Manduca moths, its pupa lacks the characteristic "jug handle" appendage.

rs. Verne and Karen Grant at the University of Texas have made detailed
observations of hawk moth behavior (Botanical Gazette144: 280-284, 1983). The
hawk moth approaches the Datura flower with its proboscis extended, lands on the
blossom, crawls onto the corolla throat, and inserts its proboscis into the nectar
canal. This is somewhat unusual because on most types of flowers hawk moths
feed from a hovering position. While feeding they often flap their wings against
the corolla throat. The proboscis becomes moist and sticky after insertion into the
nectar canal, and pollen from anthers adheres to it readily. Pollen also gets on the
head and other furry body parts. Thus pollen is transferred from one flower to
another as the moth rubs against sticky receptive stigmas at the tips of long exerted
styles. According to the Grants, hawk moths are the only flower-visiting insect
with mouthparts that fit the long, slender nectar canals of Datura wrightii.

nother fascinating aspect of the Grant's research concerns a rather

unconventional type of floral reward for hawk moths visitingDatura blossoms.
Several intoxicating alkaloids are known to occur in Datura, but heretofore have
not been correlated with pollination. Apparently Datura nectar is "spiked" with
alkaloids and the hawk moths seem to like it and come back for more. Sometimes
they arrive early and hover around the flowers, impatiently waiting for the
blossoms to "pop" open. Outside the windows at the WAYNE'S

WORDheadquarters we have observed what appear to be intoxicated moths

flying erratically around D. wrightii, clumsily landing on blossoms and crashing
into leaves or falling upon the ground. With a flashlight their eyes glow bright red
in the darkness.

lthough the coincidence of proboscis and floral lengths in hawk moths

and Datura is quite remarkable, these coadapted partners have the ability to obtain
nectar and set seeds in the absence of each other. According to Verne Grant
(Botanical Gazette 144: 439-449, 1983), hawk moths may feed on a variety of bee
flowers and hummingbird flowers, and pollen-collecting bees may
visit Datura blossoms in late afternoon and early morning. The hippo staff
at WAYNE'S WORD has observed large carpenter bees (Xylocopa) and bumble
bees (Bombus) on the blossoms of D. wrightii, busily collecting pollen from the
anthers.

lowers of some Datura species are also homogamous (stamens and pistils
mature at the same time) and are self-compatible and partially self-pollinating. It is
thus possible for one partner to migrate beyond the range of the other partner for a
time. According to Verne Grant, flexibility in the pollination system permits
migrational and evolutionary change. During times of general flower scarcity,
hawk moths are more dependent on Datura and related sphingophilous (hawk
moth-loving) blossoms because of the reliable nectar source which is unavailable
to other animals.

here are many other examples of large, white blossoms pollinated by nocturnal
hawk moths, including the fragrant gardenias of French Polynesia and South
Africa. In fact, to reach the nectar of a Madagascar orchid (Macroplectrum
sesquipedale) requires a 30 centimeter (eleven inch) proboscis. This remarkable
orchid is also known as Angraecum sesquipedale. Long before it was found in
nature, both Charles Darwin and Alfred Wallace (founding fathers of the principles
of evolution) predicted that it would be a hawk moth.

This beautiful orchid native to Madagascar is often called the "Darwin orchid"
(Macroplectrum sesquipedale), also known asAngraecum sesquipedale. In
fact, to reach the nectar of this orchid requires a 30 centimeter (eleven inch)
proboscis to penetrate the long nectar spur (white arrow). Long before it was
found in nature, both Charles Darwin and Alfred Wallace (founding fathers of
the principles of evolution) predicted that it would be a long-tongued hawk
moth.

lthough the potent alkaloids of Datura have produced untold suffering and
psychedelic binges among people through countless generations, they may also be
an ingenious strategy to insure repeat visits by long-tongued hawk moths through
the medium of drug addiction. When the moths sober up they come straight back
for more nectar. Only recently are scientists beginning to solve the mysteries of
plant toxins and how they may serve as chemical defenses or attractants, rather
than simply nonadaptive by-products of plant evolution.
See The Moth That Pollinates Jimsonweeds

The White-Lined Sphinx Moth (Hyles lineata)

Old And New World Hallucinogenic Mushrooms

ost fungi are not deadly to humans and many are perfectly edible (and are
quite delicious); however, some species are poisonous and contain potent
neurotoxins. Placing a silver coin in a pan of cooking mushrooms to see if it turns
black is not a reliable method of testing poisonous mushrooms. Unless you
understand fungal terminology and know how to use a good taxonomic key (such
as Mushrooms Demystified by David Arora, 1986), the staff at WAYNE'S
WORD does not encourage self indulgence on wild mushrooms. The beautiful,
red, fly agaric mushroom (Amanita muscaria) is unmistakable with its bright red
cap covered with white scales. It contains the toxic alkaloid, muscimol, which is
derived from ibotenic acid--an amino acid. In Europe the mushrooms were
reportedly left in open dishes to kill flies; however, according to some authorities,
the flies are merely stunned or stupefied by the toxin, and may even regain control
and fly away. Although it is poisonous to humans, there are other species
of Amanita that are much more dangerous and are potentially lethal if ingested.
Some of these dangerously poisonous species are death cap (A. phalloides), death
angel (A. ocreata), and panther amanita (A. pantherina). Fortunately these latter
deadly poisonous species are not bright red and are seldom confused with A.
muscaria; however, they may be confused with other edible mushrooms by
inexperienced gourmets. According to David Arora (Mushrooms Demystified,
1986), this species may be one of the most common causes of mushroom
poisoning in the Pacific Northwest. David Isaak (personal communication, 2002)
stated in a recent e-mail message that in the Pacific Northwest, a number of people
gather "the panther" for culinary purposes; cooking it in several changes of water
to remove "most" of the psychactive materials.
Mr. Wolffia Overindulging On Bolete Mushrooms
A Common Wild Mushroom That Can Make You Sick

hen ingested by humans, Amanita muscaria may produce visions and

delirium, and it is perhaps one of the oldest known hallucinogens. Recent studies
suggest that this mushroom was the mysterious God-narcotic "Divine Soma" of
ancient India. Thousands of years ago, Aryan conquerors who swept across India,
worshiped soma, drinking it in religious ceremonies. Many hymns in the

Indian Rig-Veda are devoted to Soma and describe the mushroom and its effects.
According to the Rig-Veda, Soma is without leaves, seeds or branches, with a head
and stalk or pillar [the structure of a mushroom]; its dazzling red skin is like the
hide of the bull [the red cap]; its dress like that of a sheep, with woolly fragments
remaining when the envelop bursts [the outer membranous envelop called the
universal veil breaks as the stalk grows upward, leaving white remnants on the red
cap]. This is a remarkably accurate description of the fly agaric mushroom (A.
muscaria). There are reports of Siberian tribesmen who ingested the mushroom to
get intoxicated. Since the active chemical (muscimol) passes through the body
relatively unaltered, others would drink the urine from these men to get high. This
way a few mushrooms could inebriate many people relatively safely and
efficiently. Lapland shamans eat fly agaric mushrooms for enlightenment, and
some authors have postulated that this may have given rise to the flying reindeer
and the red- and white-costumed Santa Claus legends.

pparently not everyone agrees that the "Divine Soma" is Amanita muscaria.
According to Terrence McKenna (Food of the Gods, 1992), the active alkaloid in
fly agaric mushrooms (muscimol) doesn't produce the psychoactive effects
described in the Rig Veda and other literature. Although the identity of the Divine
Soma was eloquently presented by R.G. Wasson in 1971 (Soma: Divine
Mushroom of Immortality), Terrence McKenna has continued to question the
effects of Amanita muscaria, and suggested other possible candidates. Based on
first-hand experience with these hallucinogens, he has suggested that a psilocybin
"magic mushroom," such asStropharia cubensis, is the true Divine Soma. In fact,
he also states that the use of mind-altering psilocybin mushrooms by ancient
humans in Africa may have been a catalyst in the development of language and
religion in primitive cultures.

manita muscaria was apparently one of the sacred hallucinogenic

mushrooms of the Incas, Mayans and Aztecs. [Other New World psychedelic
genera included Psilocybe, Paneolus, Conocybe and Stropharia]. For the Indians
of Mexico, Central and South America, partaking of these mushrooms was a
deeply religious experience, enabling them to communicate with their gods. Cortez
reported a mushroom (resembling Amanita muscaria) being eaten during the
coronation of Montezuma, and in Guatemala stone carvings dating back to 1000
BC depict curious figures with umbrella-like tops resembling the caps and stalks of
an Amanita mushroom. Mushrooms are also depicted in ancient Peruvian vessels
and in the Mexican Codices. One drawing shows an animal-like messenger from
god offering the sacred Amanita to a ruler seated on a throne. And a fresco in a
Roman Catholic Church in Plaincouralt (Indre), France depicts Adam and Eve on
either side of a tree of knowledge that is unequivocally a

branched Amanita mushroom. Some scholars believe that the original story of
Alice's Adventures in Wonderland, where Alice speaks to a green caterpillar who
is seated on a red- and white-capped mushroom, is actually the interpretation of a
mushroom experience by the author, Rev. C.L. Dodgson of Christ Church College
in Oxford (better known by his pen name of Lewis Carroll). Another
hallucinogenic "high" that is commonly depicted in paintings and children's stories
is the infamous, "politically incorrect" picture of a witch flying on a broom--the
effects of a potion made from the deadly alkaloids of several solanaceous herbs,
including jimsonweed (Datura stramonium).

New World Mushrooms Containing Natural LSD

ccording to R.E. Schultes and A. Hofmann (Plants of the Gods, 1979), a

number of other hallucinogenic mushrooms are used by shamans in Mexico,
Central and South America, including the four
genera Psilocybe, Paneolus, Conocybe and Stropharia. The exact species
selected by different shamans is determined partly by personal preference and
partly by the purpose of their use. Since mushrooms are often seasonal, their
regional availability may also be a factor in the selection process. The Aztecs
referred to these mushrooms as "teonanacatl" (flesh of the gods).

hen the Spaniards conquered Mexico, they were appalled to find the natives
worshipping their deities with the help of inebriating plants. Although the Spanish
conquerers hated and attacked the religious use of all hallucinogens, including
"peyotyl" (peyote), "ololiuqui" (morning glory), and "toloache" (Datura), they
especially resented the psilocybin mushrooms "teonanacatl." In order for the
Aztecs to carry on their cultural traditions without persecution, the use of some of
these hallucinogens went "underground." According to R.E. Schultes (1976), the
Aztecs may have tried to protect their real sacred plant (peyote) by convincing the
Spaniards that all their teonanacatl were dried mushrooms, when actually many of
the "mushrooms" were really the dried, shriveled crowns of a sacred peyote cactus.
The Spaniards first misidentified peyote as a mushroom in the sixteenth century
when they stated that the Aztec substance "teonanacatl" and peyote were the same.
It is easy to see how the Spanish authorities could have mistaken the dried crowns
or tops (buttons) of peyote cactus for the caps of teonanacatl mushrooms. The
Aztecs may have fooled their conquerers into thinking that these religious plants
were mushrooms, while the identity of one of their most spiritual and sacred plants
(peyote) was a cactus. Even in the 1900s, botanists and anthropologists concluded
that teonanacatl and peyote were the same drug. This mistake was perpetuated until

1936 when hallucinogenic mushrooms were rediscovered and definitely linked to

early Mexican ceremonies.
See Dried Psilocybe and Peyote Side-By-Side

he psychoactive alkaloid in the teonanacatl mushrooms is psilocybin, a potent

indole alkaloid (see next paragraph). Psilocin, a dephosphorylated version of
psilocybin, is about 10 times stronger. After ingestion by humans, psilocybin is
automatically converted into psilocin. Most psilocybin-containing mushrooms
have only a trace of psilocin. According to David Aurora (1986), the common
psilocibin mushroom of the Pacific coast of North America, Psilocybe
cyanescens has a higher concentration of natural psilocin and is appropriately
named "potent psilocybe." Although two of the most famous species of psilocybin
mushrooms are Psilocybe mexicana and Stropharia cubensis, there are literally
dozens of other species in the above 4 genera with similar hallucinogenic
properties. In fact, Paul Stamets (Psilocybin Mushrooms of the World, 1996)
describes all of the species and includes color photographs. Like so many LBM's
(Little Brown Mushrooms), they are difficult to identify unless you are familiar
with mushroom structure and spore taxonomy, and have a good compound
microscope at your disposal. In fact, two deadly look-alike LBM's (Galerina
autumnalis and Pholiotina filaris) resemble certain species of Psilocybe. The
small ring on their stems (called an annulus) and rusty brown spores (rather than
black spores) are "dead" give aways to avoid these potentially lethal mushrooms.

ndole alkaloids contain the

indole carbon-nitrogen ring

which is also found in the fungal
alkaloids ergine and psilocybin,
the neurotransmitter serotonin,
and the mind-altering drug LSD.
[See illustration at left showing
5-sided ring with N at the
bottom.] These alkaloids may
interfere or compete with the
action of serotonin in the brain.

Ergot: A Fungus Disease Of Rye That Contains LSD

ne of the most amazing stories about naturally-occurring alkaloids in fungi

concerns ergot (Claviceps purpurea), a fungus that infects grains of rye and
related grasses. One of the psychoactive components of ergot fungus is the alkaloid
ergine (d-lysergic acid amide), better known as natural LSD. The more potent
synthetic LSD, (d-lysergic acid diethylamide), also known as LSD 25, is one of the
most powerful psychoactive drugs known. LSD 25 was originally synthesized from
natural pshchoactive alkaloids in ergot. According to Lewis and Lewis (1977), it is
4,000 times more powerful than mescaline. Natural LSD (ergine) is also found in
the seeds of two species of Mexican morning glory vines which are still ingested
by native Indians in an important medicinal and religious ritual.

rgot forms a dark, compact, fungal mass called a sclerotium where the grain
would normally develop. One or several of these pelletlike sclerotia can be seen in
an infected grain spike, typically extending out from the bracts (glumes). When
separated from the grain spike, the sclerotia superficially resemble rat droppings
(rat pellets). The sclerotia are the source of the potent alkaloids in Claviceps
purpurea. In late spring, when rye plants are in bloom, the overwintering sclerotia
from the previous year's crop produce stalked ascocarps resembling microscopic
fungal fruiting bodies. The head of each ascocarp contains many embedded
perithecia. The perithecia contain numerous saclike asci, each with eight
ascospores. The ascospores infect the young, developing grains (ovaries) of rye
plants, eventually replacing them with purplish-black sclerotia. Because it
produces ascospores within saclike asci, Claviceps is placed in the fungal Class
Ascomycetes.
Go To The Fungal Class Ascomycetes
Cross Section Of Lichen Perithecium

uring the Middle Ages, tens of thousands of people in Europe were afflicted
with ergotism, a malady characterized by gangrenous extremities, convulsions,
madness and death. They ate rye bread infested with ergot fungus containing
several peptide alkaloids of the ergotamine group (including ergotamine, ergosine
and ergocristine) that affect blood vessels. Since they are potent vasoconstrictors,
these alkaloids can cause gangrene if ingested in sufficient dosages. Known as "St.
Anthony's Fire," ergotism was a dreaded disease in Europe. Between 990 and
1129, more than 50,000 people died of this disease in France. The disease became

so devastating that in 1093 in southern France the people formed an order to take
care of the afflicted, and they chose St. Anthony as their patron saint. One of the
symptons of the disease was an intense burning sensation, hence the name St.
Anthony's Fire. It wasn't until 1597 (500 years after the first epidemic of ergotism)
that physicians finally associated this horrendous disease with the ergot on rye.
Another form of ergot poisoning involves severe hallucinations and madness,
caused by pschoactive alkaloids in the sclerotia. [In case you are wondering,
another hallucinogenic alkaloid, mescaline, comes from the Mexican peyote cactus
(Lophophora williamsii) and the South American San Pedro cactus
(Trichocereus pachanoi), and has a chemical structure remarkably similar to the
brain neurotransmitter dopamine. Mescaline and the sacred peyote cactus are
discussed in a subsequent section.] For more information about these alkaloids
please refer to the references below, particularly those by Richard E. Schultes.

A dried grain spike of rye grass (Secale cereale) infected with ergot (Claviceps
purpurea). Some of the grains have been replaced by a dark, compact, fungal
mass called a sclerotium. The hardened sclerotia superficially resemble rat
pellets (the droppings of a rat). The sclerotia contain valuable
vasoconstricting alkaloids of the ergotamine group and lysergic acid alkaloids
which are the precursor for LSD 25 (d-lysergic acid diethylamide).

number of important medical discoveries have come from the study of ergot
fungus and ergotism. In 1935 the alkaloid ergonovine was isolated from ergot.

Since it causes strong muscular contractions, it has been used to induce labor and
to control hemmorrhaging. The alkaloid ergotamine has been used extensively to
relieve migraine headaches through the constriction of blood vessels. Thousands of
pounds of ergot sclerotia are harvested each year from midwestern rye farms, and
are used for various prescription drugs. In 1943 chemist Albert Hofmann was
studying ergot fungus, whose nuclei contain lysergic acid. When he added
diethylamide he produced lysergic acid diethylamide, better known as LSD. While
working on this new compound, Hoffman discovered that its strong hallucinogenic
effects were similar to that of natural lysergic acid alkaloids in the seeds of
"ololiuqui," morning glories used by the Aztecs in their religious ceremonies.

A Hallucinogen Alkaloid Found In Seeds & Toads

nother fascinating indole alkaloid called bufotenine occurs in the seeds of

Yopo or Paric (Anadenanthera peregrina), a South American leguminous tree
of the Orinoco River basin (not to be confused with the leguminous
genus Adenanthera). Indians of this region prepare a powder from the ground
seeds which they use as a hallucinogenic snuff. Bufotenine (5hydroxydimethyltryptamine) is a derivative of the indole alkaloid tryptamine,
which is derived from the essential amino acid tryptophan. Tryptophan is one of
the 8 (9) essential dietary amino acids in humans (which we cannot synthesize),
and is widely distributed in the animal kingdom. Interestingly enough, bufotenine
is also present in the skin secretion of certain toads of the genus Bufo, and explains
the practice of licking toads by some people. The popular dietary supplement 5HTP, sold at natural food stores, is 5-hydroxytryptophan. It is made from an
extract ofGriffonia simplicifolia seeds from coastal West Africa. 5-HTP is a
metabolic precursor of serotonin and is taken as a treatment for depression and
sleeping disorders. This herb may conflict with other antidepressant medications,
and it would be wise to consult with a knowledgeable physician before taking it.
See Fly Agaric And Psilocybe Mushrooms
Go To The WAYNE'S WORD Fungus Article
Photos Of South American Poison Dart Frogs

The Glorious Morning Glories

he morning-glory family (Convolvulaceae) contains at least 50 genera and

more than 1000 species, from high-climbing vines and woody lianas of the tropical
rain forest to prostrate, trailing perennials. They decorate our fences, trellises and
walls with lush green foliage and colorful funnel-shaped blossoms, and form
lovely green carpets of dichondra lawn. Several vines of this family provide us
with valuable and nutritious root crops, including jicama and sweet potatoes.
[Note: The common supermarket jicama sold in the U.S. comes from the
leguminous vine Pachyrhizus erosus (Fabaceae) from Mexico and Central
America.] Although the Morning-Glory Family is usually associated with climbing
vines, it also includes erect herbs, shrubs and a few trees. One unusual genus
includes the parasitic dodders (Cuscuta) which smother their host with masses of
twining, spaghetti-like orange stems. Other morning glories have invaded
cultivated fields and have become troublesome weeds. Called "bindweeds," they
literally twine themselves over other plants that happen to be in their growth path.
Some morning glories, including the infamous Mary's bean (Merremia
discoidesperma) are excellent seed voyagers and have colonized the distant
beaches of tropical islands and atolls.

eeds of two infamous Mexican morning glories, Ipomoea tricolor (syn. I.

violacea) and the white-flowered Turbina corymbosa(syn. Ipomoea burmanni),
were taken in a drink by Aztec priests in order to commune with their gods. The
ground seeds were only ingested by experienced persons who understood the
proper "spiritual dosage." The seeds from the white-flowered morning
glory Turbina corymbosa are called "ololiuqui" (pronounced o-low-lee-oo-key)
by native Indians of Mexico, and to this day provide them with an important
medicinal and religious ritual in their cultures. The black, angular seeds from the
pink-flowered Ipomoea tricolor are called "tlitliltzin." An intoxicating drink made
from the ground seeds of these species is administered by a shaman and is used by
a number of different tribes for the devine recovery of illness. This fascinating
story is explained in more detail by R.E. Schultes and A. Hofmann (1979)
in Plants of the Gods.

ike other sacred, mind-altering plants used by the Aztecs for worshipping their
gods, the use of ololiuqui was forbidden by the Spaniards. Spanish attempts to
eradicate the use of these plants resulted in secrecy by the Aztecs. As in the
teonanacatl mushrooms, the identity of the plants known as ololiuqui was shrouded
in mystery. Because of the similar, trumpet-shaped (funnel-shaped) blossoms, the
plant was thought to be Datura, a known hallucinogen still used in Mexico.
Finally in the 1930s, the seeds were clearly linked to species of morning glories.

ccording to R. E. Schultes

and A. Hofmann (1979), the

morning glory seeds contain
a lysergic acid alkaloid called
ergine (d-lysergic acid
amide), better known as
"natural" LSD. The more
potent synthetic LSD is dlysergic acid diethylamide
(see illustration at left).

ynthetic LSD has two additional ethyl groups (C2H5) and is about 100 times
more potent. Before it was discovered in morning glories, ergine was only known
from ergot (Claviceps purpurea), a rust fungus that infects grains. Psychoactive
alkaloids, such as ergine and psilocybin (from the
mushrooms Psilocybe, Stropharia, Paneolus and Conocybe) contain the indole
structure, a double carbon-nitrogen ring also found in the natural
neurotransmitter serotonin. These alkaloids may interfere or compete with the
action of serotonin in the brain, causing psychedelic visions, delusions and
hallucinations.
See Two LSD-Containing Morning Glories In Flower

Locoweeds: Wild And Crazy Plants

nlike the previous mind-altering plants, the next group to be discussed are not
taken as drugs plants. If ingested they can cause serious and permanent damage to
the central nervous system. Nonetheless, their poisonous effects on unfortunate
herbivores is quite fascinating and may lead to a better understanding of certain
human genetic disorders. These plants are most commonly associated with
abnormal behavior in livestock and other range animals, and are often referred to
as locoweeds. They belong to the large and diverse genus of flowering
plants, Astragalus. A few western locoweeds also belong to the closely related
genus, Oxytropis. Literally hundreds of different species of locoweeds grow in

almost every conceivable habitat, from coastal bluffs, grasslands and deep desert
canyons to sun-baked sand dunes and rocky alpine summits. In fact, Astragalus is
one of the largest genera of flowering plants with approximately 2,000 different
species in the northern hemisphere. Just trying to identify all the different kinds of
locoweeds in the western states can be truly overwhelming. Although most North
American species are poisonous, several kinds were apparently eaten by native
Americans and some are actually good forage plants.

ocoweeds belong to the enormous legume family (Fabaceae), along with

beans, peas, clover, alfalfa and more than 15,000 other related species. They are
sometimes called milk vetches from the notion that milk secretion in goats was
increased when they fed on the common Old World forage species (Astragalus
cicer). Like many legumes, the leaves are typically divided into a dozen or more
leaflets, and the flowers resemble small pea blossoms. Some species produce
inflated seed pods that make a distinct popping sound if you step on them.
Locoweeds are also called rattleweed because of the bladder-like, inflated pods,
particularly when a gust of wind rattles the seeds inside. Astragalus is derived
from a Greek word meaning anklebone, the plural of which means dice. Perhaps
the dice connotation refers to the rattling of seeds inside papery pods, like the
sound of dice in a thrower. In anatomy, the astragalus or talus is one of seven
bones in the ankle joint. Anklebones were apparently used for dice by ancient
Greeks, and to this day, veteran crapshooters in Las Vegas refer to dice as "bones."
Since adult astragalus bones are a little too large for dice, some of the smaller,
cuboidal or cuneiform anklebones were probably used.

any species of locoweeds native to the western United States are known to be
poisonous to livestock (L.F. James, Noxious Range Weeds, 1991). The actual
mechanism of locoweed poisoning may involve: (1) Toxic levels of selenium
absorbed from the soil, (2) nitrogen-containing sugar compounds called
nitroglycosides, and (3) potent swainsonine alkaloids causing a condition called
"locoism." According to P.R. Cheeke and L.R. Shull (Natural Toxicants in Feeds
and Poisonous Plants, 1985), of the 372 species of Astragalusin North America,
about 25 species contain toxic levels of selenium, 263 contain poisonous
nitroglycosides, and 13 cause locoism. Some of the poisonous species may be
placed in more than one of the above three categories. Bee keepers in Nevada have
reported serious honey bee losses after working the flowers of spotted locoweed
(Astragalus lentiginosus). The toxicity of Astragalus to bees is unusual because
relatively few plants produce nectar or pollen which is poisonous to honey bees.
The notoriously toxic "diablo locoweed" (A. oxyphysus) is well-known in
California and some ranchers have attempted to eradicate it from their property.
Apparently it wasn't removed from all grazing land because several years ago the
editor of WAYNE'S WORD observed a deceased steer lying in a pasture
containing this locoweed in Kern County.

ome species of Astragalus accumulate toxic levels of selenium and often have
a peculiar malodorous foliage. In fact, specimens of A. bisulcatus and the desert
species A. crotalariae can produce the dominant scent in herbarium cabinets for
many years. Locoweed indicators of selenium-rich soils are sometimes referred to
as "poison vetches," and may contain selenium levels of several hundred to 10,000
ppm (parts per million) (P.R. Cheeke and L.R. Shull, 1985). Several names have
been applied to selenium poisoning in cattle, including "blind staggers" and "alkali
disease." In severe cases, the animals become lame and emaciated, and often fall
into a kneeling position from which they are unable to rise. Toxic levels of
selenium also occur in other wild plants of western North America, such as species
of Stanleya, colorful shrubby perennials in the mustard family (Brassicaceae).
Selenium poisoning of fish and waterfowl from has been well documented in
California's Central Valley. In the human body, the trace element selenium is
needed for the function of certain enzymes, and may serve as a cellular antioxidant
thought to suppress certain tumors (M.A. Weiner and J.A. Weiner, Herbs That
Heal, 1994). Natural sources of selenium come from the allium vegetables,
including onions and garlic.

he majority of locoweed species poisonous to livestock contain toxic

nitroglycosides. The extreme toxicity of nitroglycosides, such as miserotoxin, in
livestock is caused by the production 3-nitropropionic acid (NPA) through a

complex metabolic pathway involving enzymes of rumen microbes and the liver
(W. Majak and M.A. Pass, Toxicants of Plant Origin , 1989). Another toxic
reaction involves the oxidation of hemoglobin by nitrites produced by the
hydrolysis of miserotoxin. The oxidized hemoglobin (called methemoglobin) is
incapable of carrying oxygen. NPA is lethal to animals because it inhibits the vital
enzyme succinate dehydrogenase inside mitochondria, thus blocking ATP
synthesis and ultimately causing cellular death (M.A. Pass, Plant-Associated
Toxins, 1994). In some animals with different gastrointestinal microbes, such as
rats and rabbits, the miserotoxin is not converted into lethal NPA; however, studies
indicate that death in rabbits is due to nitrite poisoning (W. Majak and M.A. Pass,
1989). Symptoms of acute livestock poisoning involve general weakness and loss
of neural control, convulsions, blindness, coma, and death. More than 200 species
of Astragalus in North America contain nitroglycosides, including A. cibaria, A.
falcatus, and A. miser. The latter species has also been known to cause high
mortality in foraging honey bees.

ne of the most destructive types of livestock poisoning by locoweed ingestion

is called "loco disease" or locoism. It is caused by at least two very potent
indolizidine alkaloids, swainsonine and swainsonine-N-oxide, and impels horses
and cattle to act in a wild and crazy manner. Some authorities only apply the term
"locoweed" to species of Astragalus and Oxytropis containing these alkaloids,
such as A. lentiginosus, A. mollissimus, A. wootonii, O. lambertii, and O.
sericea. Swainsonine was originally isolated from the Australian darling pea
(Swainsona) and more recently from the spotted locoweed (Astragalus
lentiginosus) (R.J. Molyneux and L.F. James, Loco Intoxication: Indolizidine
Alkaloids of Spotted Locoweed, 1981). Consumption of locoweeds for two weeks
to a month is necessary before obvious signs of poisoning are evident (L.F. James
and K.E. Painter, Locoweed Poisoning in Livestock, 1989). Animals suffering
from locoism may exhibit depression, a staggering gait, and general muscular
incoordination. They may withdraw from other animals and become solitary. The
final stages are characterized by difficulty in eating or drinking, paralysis and
death. Afflicted animals often become nervous, or easily aggravated, and exhibit a
complete loss of depth perception. There are reports of animals being injured or
killed by running through fences or falling into ponds and streams. When plenty of
other forage is available, animals tend to avoid locoweed; however, poisoned
animals apparently acquire a taste for it and actually seek it out (P.R. Cheeke and
L.R. Shull, 1985).

he cause of locoism at the cellular level is very complex. The swainsonine

alkaloids inhibit or tie up the key enzyme mannosidase resulting in the
accumulation of mannose sugar in nerve cells and irreparable damage to brain

tissue (P.R. Dorling, C.R. Huxtable and P. Vogel, Neuropathology and Applied
Neurobiology, 1978). This condition is remarkably similar to a genetic deficiency
of the same vital enzyme in humans called mannosidosis (P.A.
Ockermann, Mannosidosis, 1973). Mannosidosis is a genetic disorder called a
lysosomal storage disease, in which cells of the central nervous system become
filled with cytoplasmic vacuoles of mannose due to the lack of the vital enzyme
mannosidase that is essential in breaking down mannose. The actual vacuoles are
swollen organelles called lysosomes where the enzymatic breakdown process
normally occurs. Lysosomal storage diseases, such as mannosidosis, are often
caused by recessive genes and result in paralysis and death within a few years
following birth. Perhaps one of the better known storage diseases is Tay Sachs
Disease, in which nerve cells fill up with a lipid called ganglioside or GM2
because they lack the vital enzyme HEX A needed to break down GM2. Studies of
the biochemical effects of locoweed poisoning on the central nervous system of
cattle may lead to a better understanding of these tragic human neurological
disorders.

ative American Indians were apparently aware of the poisonous properties of

some locoweeds and avoided them. Other drug plants are occasionally called
locoweeds, such as the hallucinogenic jimsonweed (Datura), and some of these
were commonly utilized by Indians during ceremonial rituals. In the southwest,
Cahuilla Indians utilized the pods of at least one unknown Astragalus locoweed
(J.L. Bean and K.S. Saubel, Temalpakh: Cahuilla Indian Knowledge and Usage
of Plants, 1972). The pods were pounded up and mixed with beans and other
foods, perhaps as a spice or flavor enhancer. An Arizona locoweed (A.
ceramicus), with beautiful brown-mottled pods, produces sweet, edible rootstocks
which are reportedly eaten in spring by Hopi children. Another locoweed of the
prairie and plains states (A. crassicarpus) produces edible fleshy pods (K.
Kindscher, Edible Wild Plants of the Prairie: An Ethnobotanical Guide, 1987).
It is known locally as ground plum, Indian pea, or buffalo bean, and the pods were
eaten, raw or cooked, by Indians and white settlers. The perennial roots of three
species, including A. canadensis, A. caryocarpus, and A. pictus-filifolius, were
eaten raw or cooked by Blackfoot Indians of Montana and Hopi of Arizona. Not all
locoweeds are poisonous to people; however, because of the difficulty in
identifying some species, it would definitely NOT be advisable to try any of them
in gourmet dishes. It would actually be easier to select edible mushrooms from the
deadly species, especially with all of the pictorial mushroom guides available
today.
See Locoweeds And A Dead Steer

The Mescal Bean And Peyote Cactus

robably the most famous New World hallucinogenic plant is peyote

(Lophophora williamsii), a small, spineless cactus native to the Rio Grande valley
of Texas and the northern and central parts of the Mexican plateau region. Another
species (L. diffusa) is native to the Mexican state of Queretaro. The rounded, graygreen stem crown (top) is radially-divided into sections, each bearing a small
meristematic region (called an areole) from which arises a tuft of hairs. The crown
tapers into a thick carrot-like root that extends into the ground.

alled "peyotyl" by the Aztecs, this was truly a sacred plant used in religious
ceremonies where they communicated with their gods. The spiritual, religious
usage of peyote persists to this day by the Tarahumara, Huichol and other Mexican
Indians, as well as by members of the Native American Church in the United
States and western Canada. The Indians cut off the crowns and sun-dry them into
brown, mushroom-shaped "mescal buttons" that last for long periods and can be
shipped to distant places for use. After the crown (button) dries, the soft, fleshy
tissue is reduced in volume. For this reason the tufts of hairs appear much larger
and occupy a larger proportion of the button. The Aztec word peyotyl means
"caterpillar cocoon," referring to the white, woolly tufts of hairs. When the top is
severed, the plant often resprouts with new crowns so that many-crowned peyote
plants are common. Except for the woolly hairs, the dried, peyote buttons
superficially resemble the cap of a dried mushroom.

panish conquerers tried to ban the use of peyote by native Indians. By 1720 the
eating of peyote was prohibited throughout Mexico, but peyote was so strongly
rooted in native Indian lore that its use actually spread to other tribes. The Spanish
thought the peyote buttons used by Aztecs were mushrooms, and it wasn't until the
1930s that researchers finally discovered that the Aztecs were actually using both
peyote (peyotyl) and psilocybin mushrooms (teonanacatl) in their religious
ceremonies.

he peyote cactus contains more than 50 different alkaloids, but the most active
hallucinogen is mescaline. The chemistry, botany and history of peyote is
discussed in a fascinating book by E.F. Anderson (Peyote: The Divine Cactus,
1976). Mescaline has a chemical structure similar to the brain neurotransmitter
dopamine. It is also structurally similar to the neurohormone norepinephrine
(noradrenalin) and to the stimulant amphetamine. In the peyote cactus, mescaline is

formed in a complex pathway from the amino acid tyrosine. A similar pathway in
humans produces epinephrine (adrenalin) and its demethylated precursor
norepinephrine from tyrosine. Dopamine and its precursor L-dopa are also derived
from a tyrosine pathway. The following illustration shows the remarkable
molecular similarity between mescaline and dopamine:

escaline also occurs in several other cactus species, including the commonly

cultivated, night-blooming, South American San Pedro cactus (Trichocereus

pachanoi). In the Andes of Peru, Ecuador and Bolivia the natives call this tall,
columnar cactus "aguacolla" or "giganton." An intoxicating drink called "cimora" is
made from the boiled stems. According to R.E. Schultes (1976), the drink may be
spiked with other potent hallucinogens, including species of Brugmansia (Datura).
The cut stems are sometimes seen in market places of the northern Peruvian
Andes in neatly stacked piles. There are about 25 species of Trichocereus native
to South America. They are typically large, tree-like cacti with cylindrical, ribbed
stems and large, nocturnal, white blossoms. Other species within this fascinating
genus may also contain mescaline.
See A Beautiful San Pedro Cactus In Full Bloom
Another Beautiful Night-Blooming San Pedro Cactus

ontrary to popular rumors, mescaline is not found in the bright red, poisonous
seeds of the beautiful, drought-resistant shrub called mescal bean (Sophora
secundiflora); however, they do inhabit a similar range in the arid lands of the
southwestern United States and Mexico. Mescaline is also not related to the highly
intoxicating beverage called "mescal" or "mezcal," made from the fermented and
distilled juices of several North American species of Agave, including A.
americana and A. atrovirens. Incidentally, the fermented juice is called pulque,
and the highly-alcoholic distilled products include mezcal and tequila. The seeds of
mescal bean contain another potent and dangerously poisonous alkaloid, cytisine,
which was ingested by some North American Indian tribes in a vision-seeking

"Red Bean Dance" prior to the widespread use of peyote. According to R.E.
Schultes (1976) mescal beans have been discovered in Indian sites dating before
AD 1000, and from one site dating back to 1500 BC. In fact, to this day the leader
of the peyote ceremony in some of these tribes (called the "roadman") wears a
necklace made from bright red mescal beans. [For biology students, cytisine is not
to be confused with the pyrimidine base cytosine found in DNA and RNA.]

ne of the most interesting stories concerning the use of peyote north of

Mexico concerns Quanah Parker, son of a Comanche war chief (Nokoni) and
Cynthia Parker (a white woman who was captured by the Indians). [For more
information about this remarkable man, please refer to B. Neeley (1995) The Last
Comanche Chief: The Life and Times Of Quanah Parker, and Weston La Barre
(1975)The Peyote Cult.] In 1884, Quanah Parker became seriously ill and was
treated by a Mexican curandera. Quanah regained his health and recognized that
peyote could be a useful factor in binding his people together. The latter half of the
19th century (post Civil War period) was a time of turmoil and humiliation for the
American Indian tribes. Their pristine hunting lands were gradually being taken
away from them; they were swindled by federal authorities; they were forced to
move to reservations far from their homes; they were forced to attend schools that
denied their heritage; they were corrupted by the white man's "firewater" (alcohol);
and they had Christianity forced upon them by missionaries. Quanah fashioned a
series of ceremonies, with cultural elements from Comanche, Kiowa, Apache, and
parts of Christianity. This was a good time for the peyote religion--to bring native
people dignity and hope of survival, and to bring them spiritual sustenance. The
peyote religion spread rapidly during the late 1800s and early 1900s. With the
assistance of James Mooney, an ethnologist with the Smithsonian Institution, the
Native American Church was finally established in 1918. According to Benjamin
Capps (The Great Chiefs, 1975), Quanah Parker once said to a white
listener: "The white man goes into his church house and talks about Jesus; the
Indian goes into his teepee and talks to Jesus."
See The Mescal Bean And Peyote Cactus

References About Plant Alkaloids:

1. Arora, D. 1986. Mushrooms Demystified (Second Edition). Ten Speed
Press, Berkeley, California.
2. Anderson, E.F. 1980. Peyote: The Divine Cactus. The University of
Arizona Press, Tucson, Arizona.
3. Bean, L.J. and K.S. Saubel. 1972. Temalpakh: Cahuilla Indian

Knowledge and Usage of Plants. Malki Museum Press, Banning,

California.
4. Cheeke, P.R. and L.R. Shull. 1985. Natural Toxicants in Feeds and
Poisonous Plants. Avi Publishing Co., Inc., Westport, Conn.
5. Dewitt, D. and P.W. Bosland. 1996. Peppers of the World: An
Identification Guide. Ten Speed Press, Berkeley, California.
6. Dorling, P.R., Huxtable, C.R. and P. Vogel. 1978. "Lysosomal Storage
in Swainsona spp. Toxicosis: An Induced
Mannosidosis." Neuropathology and Applied Neurobiology 4: 285295.
7. Fuller, T.C. and E. McClintock. 1986. Poisonous Plants of California.
University of California Press, Berkeley, California.
8. Grant, V. 1983. "The Systematic and Geographical Distribution of
Hawkmoth Flowers in the Temperate North American Flora." Botanical
Gazette 144: 439-449.
9. Grant, V. and K. A. Grant. 1983. "Behavior of Hawkmoths On Flowers
of Datura meteloides." Botanical Gazette 144: 280-284.
10. Harner, M.J. (editor). 1973. Hallucinogens and Shamanism. Oxford
University Press, New York.
11. James, L.F. 1991. Noxious Range Weeds. Westview Press, Boulder,
Colorado.
12. James, L.F. and K.E. Painter. 1989. "Locoweed Poisoning in Livestock."
Chap. 3 in: Swainsonine and Related Glycosidase Inhibitors, L.F. James
et al., eds. Iowa State University Press, Ames, Iowa.
13. Janzen, D.H. 1983. Costa Rican Natural History. The University of
Chicago Press, Chicago, Illinois.
14. Janzen, D.H. 1974. "Swollen-Thorn Acacias of Central
America." Smithsonian Contributions to Botany Number 13.
Smithsonian Institution Press, Washington, DC.
15. Kindscher, K. 1987. Edible Wild Plants of the Prairie: An
Ethnobotanical Guide. University Press of Kansas.
16. La Barre, W. 1975. The Peyote Cult (Fourth Edition Enlarged). Archon
Books (The Shoe String Press, Hamden, Connecticut).
17. Lewis, W.H. and M.P.F. Elvin-Lewis. 1977. Medical Botany. John Wiley
and Sons, Inc., New York.
18. Majak, W. and M.A. Pass. 1989. "Aliphatic Nitrocompounds." Chap. 5
in: Toxicants of Plant Origin: Vol. II Glycosides, P.R. Cheeke, ed. CRC
Press, Inc., Boca Raton, Florida.
19. McKenna, T. 1992. Food of the Gods. Bantam Books, New York.
20. Molyneux, R.J. and L.F. James. "Loco Intoxication: Indolizidine Alkaloids

of Spotted Locoweed (Astragalus lentiginosus)." Science 216: 190-191.

21. Neeley, B. 1995. The Last Comanche Chief: The Life And Times of
Quanah Parker. John Wiley, New York.
22. Pratt, W.B. and R.W. Ruddon. 1979. The Anticancer Drugs. Oxford
University Press, New York.
23. Raffauf, R.F. 1996. Plant Alkaloids: A Guide To Their Discovery and
Distribution. Hawkworth Press, Inc., New York.
24. Schultes, R.E. 1976. Hallucinogenic Plants. Golden Press, New York.
25. Schultes, R.E. 1973. The Botany and Chemistry of Hallucinogens.
Charles C. Thomas, Springfield, Illinois.
26. Schultes, R.E. and A. Hofmann. 1979. Plants of the Gods. McGraw-Hill
Book Company, New York.
27. Stamets, P. 1996. Psilocybin Mushrooms of the World. Ten Speed
Press, Berkeley, California.
28. Stebbins, G.L. 1974. Flowering Plants: Evolution Above The Species
Level. Belknap Press of Harvard University Press, Cambridge, Mass.
29. Stewart, O.C. 1987. Peyote Religion: A History. University of Oklahoma
Press, Norman, Oklahoma.
30. Wasson, R.G. 1971. Soma: Divine Mushroom of Immortiality. Harcourt
Brace Jovanovich, New York.
31. Weiner, M.A. and J.A. Weiner. 1994. Herbs That Heal. Quantum Books,
Mill Valley, California.