Pharmacognosy of Hallucinogenic plants

1. Hallucinogens
Part 2
Dr. S.T.V.Raghavamma

2. Fungi:
Amanita muscaria, commonly known
as the fly agaric or fly amanita,
muscimol mushroom.
Family: basidiomycete
Genus : Amanita.
GD: Native throughout the temperate
and boreal regions of the Northern
Hemisphere.
• in the Southern Hemisphere,
generally as a symbiont with pine and
birch plantations, and is now a true
cosmopolitan species, associated with
deciduous and coniferous trees.

3. • main psychoactive constituents:
1. ibotenic acid and muscimol.
2. Muscarine
3. Muscazone
• Muscimol is known to be psychoactive compound.
• ibotenic acid, a neurotoxin serves as a prodrug
tomuscimol.
• 10–20% ibotinic acid converts to muscimol after
ingestion

4. muscimolIbotenic acid
muscarine

5. • Spring and summer mushrooms have been reported to
contain up to 10 times more ibotenic acid and
muscimol than autumn fruitings.
• approximately 6 mg muscimol or 30 to 60 mg
ibotenic acid; this is typically about the amount found
in one cap of Amanita muscaria.

6. • The active constituents of this species are water-
soluble, and boiling and then discarding the cooking
water at least partly detoxifies A. muscaria.
• Drying may increase potency, as the process
facilitates the conversion of ibotenic acid to the more
potent muscimol.
• once detoxified, the mushroom becomes edible

7. 2.
• Muscarine has been found in harmless trace amounts
• A. muscaria fruitbodies contain a variable dose of muscarine,
usually around 0.0003% fresh weight.
• This is very low and toxicity symptoms occur very rarely.
• Inocybe and Clitocybe contain muscarine concentrations up to
1.6%.

8. • Muscazone :
• more recently been isolated from European
specimens of the fly agaric.
• It is a product of the breakdown of ibotenic acid
by ultra-violet radiation
• Muscazone is of minor pharmacological activity
compared with the other agents

9. muscimolIbotenic acid
muscarine

10. • Pharmacology:
• Muscarine binds with muscarinic acetylcholine
receptors leading to the excitation of neurons bearing
these receptors.
• ibotenic acid and muscimol are structurally
related to each other and to two
major neurotransmitters of the central nervous
system: glutamic acid and GABA respectively.

11. • Ibotenic acid and muscimol act like these
neurotransmitters.
• muscimol being a potent GABA agonist while
ibotenic acid is an agonist of NMDA glutamate
receptors and certain metabotropic glutamate
receptors which are involved in the control of
neuronal activity.
• It is these interactions which are thought to cause the
psychoactive effects found in intoxication.

12. Psilocybe mexicana
• Its first known usage was by the
natives of Central
America and North America over
2,000 years ago.
• Kingdom: Fungi
• Division: Basidiomycota
• Class: Agaricomycetes
• Order: Agaricales
• Family: Strophariaceae
• Genus: Psilocybe
• Species: P. mexicana

13. • Psilocybin is the psychedelic prodrug found in most potent are
members of the genus Psilocybe such as P. azurescens P. semilanceata
and P. cyanescens but psilocybin has also been isolated from about a
dozen other genera
• As a prodrug psilocybin is quickly converted by the body to psilocin
which has mind-altering effects similar, in some aspects, to those
of LSD, mescaline and DMT
Psilocybin

14. In general, the effects include
• euphoria
• visual and mental hallucinations
• changes in perception
• a distorted sense of time
• spiritual experiences,
• possible adverse reactions such as nausea
and panic attacks

15. Pholiotina cyanopus
• genus Pholiotina also the psychoactive
compound psilocybin.
• Originally described as Galerula
cyanopus by American mycologist George
Francis Atkinson in 1918.
• It was transferred to Conocybe by Robert
Kühner in 1935 before being transferred
to Pholiotina by Rolf Singer in 1950.
• Kingdom: Fungi
• Division: Basidiomycota
• Class: Agaricomycetes
• Order: Agaricales
• Family: Bolbitiaceae
• Genus: Pholiotina
• Species: P. cyanopus

16. • Pholiotina cyanopus hallucinogenic:
• psilocin
• psilocybin,
• baeocystin,
• norbaeocystin and Psilocin also known as 4-HO-DMT, 4-hydroxy
DMT, psilocine, psilocyn, or psilotsin
• aeruginascin
• fruit bodies of P. cyanopus have been found to contain anywhere from 0.33–
1.01% (of dry weight) psilocybin, 0–0.007% psilocin, and 0.12–0.20%
baeocystin.
• Most mycologists recommend against eating this mushroom because it is easy
to mistake for poisonous species.

17. • Psilocin and psilocybin, hallucinogenic principles contained in
certain mushrooms, notably the two Mexican species Psilocybe
mexicana and P. cubensis (formerly Stropharia cubensis).
• Hallucinogenic mushrooms used in religious ceremonies by the
Indians of Mexico were considered sacred and were called “god’s
flesh” by the Aztecs.
• In the 1950s the active principles psilocin and psilocybin were
isolated from the Mexican mushrooms.
• As a result of their subsequent recreational abuse, psilocin and
psilocybin and the mushrooms that contain them came under
strict regulatory control.

18. • Uses:
• Psilocin and psilocybin are not used in modern medicine, but
research suggests that they may have potential applications in
the treatment of anxiety and in the improvement of quality of
life for terminally ill patients.

19. • Pharmacology:
• Chemically, psilocin and psilocybin are indole hallucinogens
that alter the action of serotonin (an indole
amine neurotransmitter) in brain tissue.
• Psilocybin differs from psilocin in having a phosphate group
attached to the molecule at the oxygen atom
.

20. Psilocybe cubensis
• previously known
as Stropharia cubensis
• psychedelic
mushroom whose principal
active compounds
are psilocybin and psilocin
• Commonly called shrooms,
magic mushrooms, golden
tops, cubes, or gold caps,
Family: Hymenogastraceae
Psilocybe cubensis
Scientific classification
Kingdom: Fungi
Division: Basidiomycota
Class: Agaricomycetes
Order: Agaricales
Family: Hymenogastraceae
Genus: Psilocybe
Species: P. cubensis

21. Lycoperdon
• Lycoperdon
• classification
• Kingdom: Fungi
• Division: Basidiomycota
• Class: Agaricomycetes
• Order: Agaricales
• Family: Agaricaceae
• Genus: Lycoperdon

22. • Chemical compound:
• The amino acid lycoperdic acid (chemical name 3-
(5(S)-carboxy-2-oxotetrahydrofuran-5(S)-yl)-2(S)-
alanine)
• Based on the structural similarity of the new amino
acid with (S)-glutamic acid, (S)-(+)-lycoperdic acid is
expected to have antagonistic or agonistic activity for
the glutamate receptor in the mammalian central
nervous system.

23. LSD- lysergic acid diethylamide
LSD was first synthesized in 1938, by Albert Hofmann, a chemist working
on natural products at the Sandoz AG pharmaceutical company in Basel,
Switzerland.
As an attempt to synthesize a circulatory and respiratory stimulant derived
from ergot, he synthesized LSD.
He tried it in experimental animals and found it caused restlessness and had
effects on the uterus.
LSD can be termed an ‘entheogen’, which means that the user feels ‘as if
the eyes have been cleansed and the person could see the world as new in all
respects’

24. • LSD is one of the most potent, mood-changing, semi-synthetic
psychedelic agent.
• The popular street names are: Acid, Stamp, Lucy, Microdots, Purple
Heart, Sunshine, Heavenly Blue, and so on.
• Effects: The usual mental effects are
• delusions,
• visual hallucinations,
• distortion of sense of time and identity,
• impaired depth and time perception,
• artificial sense of euphoria or certainty,
• distorted perception of the size and shape of objects,
• movements, color, sounds, touch and the user’s own body image,
• severe, terrifying thoughts and feelings, f
• ear of losing control,
• fear of death, panic attacks, and so on

25.  Ipomoea contains psychoactive compounds,
mainly alkaloids.
• Kiribadu Ala (giant potato, I. mauritiana) is one of the many
ingredients of chyawanprash, the ancient Ayurvedic tonic called
"the elixir of life" for its wide-ranging properties.

26. • Kingdom: Plantae
• Clade: Angiosperms
• Clade: Eudicots
• Clade: Asterids
• Order: Solanales
• Family: Convolvulaceae
• Tribe: Ipomoeeae
• Genus: Ipomoea

27. • Other species were and still are used as
potent entheogens .
• Seeds of Mexican morning glory I. tricolor (I.
violaceae) were thus used. It has similar constituents
like Rivea corymbosa.
• Beach moonflower (I. violacea) was also used thus,
and the cultivars called 'Heavenly Blue Morning
Glory', touted today for their psychoactive properties,
seem to represent an indeterminable assembly
of hybrids of these two species.
• Japanese morning glory I. hederacea seeds are used
as pergetive and officialin B.P as kaladana/pharbitis
seeds

28. Hallucinogenic components:
of I. tricolor, I. violacea and/or purple morning glory (I.
purpurea):
• Ergoline derivatives (lysergamides),
• Ergine (LSA),
• isoergine,
• D-lysergic acid N-(α-hydroxyethyl)amide
• Lysergol

29. • Medical uses:
• Ergonovine enhances the action of oxytocin, used to
still post partum bleeding.
• Ergine induces drowsiness and a relaxed state and
might be useful in treating anxiety disorder.

30. Peyote /Lophophora williamsii
peyote is a small,
spineless cactus with psychoactive
alkaloids particularly mescaline.
• Peyote is a Spanish word meaning
"glisten" or "glistening".
• Also known as anhalonium/mescal
bottons.
 GD:
• Peyote is native to Mexico and
southwestern Texas.
• It is found primarily in
the Chihuahuan Desert.

31.  Chemical constituents:
• Peyote contains of phenethylamine alkaloids.
• The principal one is mescaline for which the content
of Lophophora williamsii is about 0.4%
fresh (undried) and 3–6% dried
• Mescaline

32. • Mono and di ,tri oxygenated phenethyl amines and their
amides
• Tetrahydoisoquinoline alkaloids and their amides– anhalonin.
• Phenylethyl amine derivatives and their conjugates
• Pyrrole derivatives

33. Indian hemp
• Source: Cannabis sativa- indian hemp; C. indica; C. ruderalis
 cannabis preparations include:
• Charas (resin),
• Ganja (flower), and
• Bhang (seeds and leaves), with a milkshake made from bhang
being one of the most common legal usages

34. 1. Ganja, a Hindi and Nepali name for hemp, is derived
from the word ganjha (from the Sanskrit gañjā)
referring to a "powerful preparation of cannabis
sativa.
• Ganja: (Bombay-ganja) I.P 1955- contain not more
than 10% of its fruits,large leaves and stems of 3mm.
• Round / bengal ganja is prepared by rolling the wilted
tops between the hands.

35. 2. Bhang: it is an edible preparation of cnnabis.
It contains large leaves and twigs of both male and
female plants.
Used in india for smoking or in the form of electuary
made by digestion with melted butter.

36. 3. Charas/ churrus : it is the crude resin
• Charas (Hindustani) is the name given to a hashish form
of cannabis which is handmade in the Indian
subcontinent and Jamaica.
• It is made from the resin of the cannabis plant (Cannabis
sativa or Cannabis indica)
• The difference between charas and hashish is that
hashish is made from a dead cannabis plant and charas is
made from a live one.

37. • During hand-harvesting, live cannabis plants' flowering buds (as opposed
to dried plants/buds) are rubbed between the palms of the harvesters' hands,
and by the end of the day one has perhaps 8 or 9 grams of charas.
• The faster one works, the lower the quality of charas; hence to make
"Malana cream" it is necessary to go very slowly and make only a few
grams a day.
• Nowadays production of cannabis in the Himalayas has increased with
growing demand for Malana cream;

38. • Chemical constituents:
• narcotic resin is soluble in alcohol, ether and carbon disulphide.
• Cannabinoids – with C11-C12aromatic portion derived from six
acetate units and an isoprenoid component C10.
• Cannabinol (CBN),
• Δ9-Tetrahydrocannabinol (Δ9-THC)- potent psychoactive
• Cannabidiol (CBD)
• Cannabidiol- carboxilic acid, cannabigerol
• Cannabichromene
• cannabipinol

40. Cannabichromene

41. • Narcotic and fiber classification of plant is based on
waller relation ship
Δ9-THC + CBN
CBD
• If it is equal to 1= a drug type of cannabis
• If less than 1 = a fiber type

42.  Medicinal use:
• Hypotonic
• anticonvulsant
• Anti-anxiety
• Antitussive
• Used in human and veterinary medicine
• THC relives nausea and vomiting

43. Nutmeg and mace:

44. Virola spp:
• closely related to
Myristicaceae such as nutmeg
N,N-dimethyltryptamine(DMT)
5-hydroxy- DMT, 5-methoxy DMT, 2-methyl-
1,2,3,4-tetrahydro-β-carboline.

45. Derivatives of DMT
DMT N -methyltryptamine