Pharmakon · Archive view
The Compounds
The chemistry axis of the archive
The same archive read chemically: 17 compound families across 26 plants. A shared molecule is a real historical connector — the tryptamine thread alone runs from Amazonian snuffs to Mazatec morning-glories — but chemistry never exhausts the rite: each family links back to the living traditions that carry it.
Mescaline
2 plants — Echinopsis pachanoi · Lophophora williamsii
3-Methoxytyramine
C₉H₁₃NO₂
4-(2-aminoethyl)-2-methoxyphenol
VARIABLE
ALKALOID
FIELD
ALKALOID
FIELD
Other reported alkaloids
3,4-dimethoxyphenethylamine · tyramine · hydroxy-dimethoxyphenethylamines · anhalonidine/anhalinine
Presence and abundance depend on specimen and method.
Tryptamine (DMT & relatives)
8 plants — Acacia · Anadenanthera colubrina · Anadenanthera peregrina · Diplopterys cabrerana · Mimosa tenuiflora · Phalaris · Psychotria viridis · Virola theiodora
Other constituents
Indole N-oxides · bufotenidine · tannins · flavonoids
Strongly tissue-dependent chemistry
Related indoles
N-oxides · N-methyltryptamines · serotonin derivatives
Tissue- and specimen-dependent
β-carboline (MAOI)
2 plants — Banisteriopsis caapi · Peganum harmala
Tetrahydroharmine
C₁₃H₁₆N₂O · PubChem 159809 →
2,3,4,9-tetrahydro-7-methoxy-1-methyl-1H-pyrido[3,4-b]indole
Ibogaine
1 plant — Tabernanthe iboga
Ibogaine
C₂₀H₂₆N₂O
12-methoxyibogamine
Ibogamine
C₁₉H₂₄N₂
Parent iboga alkaloid scaffold
Tabernanthine
C₂₀H₂₆N₂O
Methoxyibogamine positional isomer
Voacangine
C₂₂H₂₈N₂O₃
Carbomethoxy-methoxy iboga alkaloid
Salvinorin A
1 plant — Salvia divinorum
Salvinorin A
C₂₃H₂₈O₈
Trans-neoclerodane diterpenoid
Salvinorin B
C₂₁H₂₆O₇ · CAS 92545-30-7
Deacetylated salvinorin
Salvinorin C
C₂₅H₃₀O₉
Minor diacetylated neoclerodane
Salvinorins D–J
Neoclerodane series
With divinatorins and salvinicins
Nicotine
1 plant — Nicotiana rustica
Nicotine
C₁₀H₁₄N₂
Principal alkaloid; agonist at neuronal nicotinic acetylcholine receptors.
Nornicotine
C₉H₁₂N₂
Minor alkaloid and nicotine metabolite; proportion may increase during curing.
Anatabine
C₁₀H₁₂N₂
Minor pyridine alkaloid; nicotinic-receptor activity is weaker than nicotine.
Anabasine
C₁₀H₁₄N₂
Minor piperidine alkaloid with peripheral and central nicotinic activity.
Ergot alkaloids
1 plant — Claviceps purpurea
Ergotamine
C₃₃H₃₅N₅O₅
Ergopeptine · lysergic acid–tripeptide cyclol
Ergometrine / ergonovine
C₁₉H₂₃N₃O₂
Simple lysergic acid amide
Ergocristine
C₃₅H₃₉N₅O₅
Ergopeptine alkaloid
Ergine / LSA
C₁₆H₁₇N₃O
Lysergic acid amide
Cocaine
1 plant — Erythroxylum coca
Cocaine
C₁₇H₂₁NO₄
Benzoylmethylecgonine · tropane ester
Cinnamoylcocaine
C₁₉H₂₃NO₄
Methylecgonine cinnamate · geometric isomers occur
Tropacocaine
C₁₅H₁₉NO₂
Benzoyltropine · tropane ester
Hygrine
C₈H₁₅NO
N-methylpyrrolidinyl ketone
Ergine (LSA)
1 plant — Ipomoea corymbosa
Ergine · LSA
C₁₆H₁₇N₃O
D-lysergic acid amide · lysergamide
Lysergic acid α-hydroxyethylamide
C₁₈H₂₁N₃O₂
LAH / LSH · N-(1-hydroxyethyl)lysergamide
Ergometrine · ergonovine
C₁₉H₂₃N₃O₂
Lysergic acid propanolamide
Chanoclavine-I
C₁₆H₂₀N₂O
Tricyclic clavine alkaloid
Mitragynine
1 plant — Mitragyna speciosa
Mitragynine
C₂₃H₃₀N₂O₄
Major corynanthe-type monoterpenoid indole alkaloid
7-Hydroxymitragynine · 7-OH
C₂₃H₃₀N₂O₅
Oxidised minor alkaloid and active mitragynine metabolite
Speciociliatine
C₂₃H₃₀N₂O₄
C-3 epimer of mitragynine
Paynantheine
C₂₃H₂₈N₂O₄
Corynanthe-type indole alkaloid
Opiate alkaloids
1 plant — Papaver somniferum
Morphine
C₁₇H₁₉NO₃ · PubChem 5288826 →
(4R,4aR,7S,7aR,12bS)-3-methyl-2,4,4a,7,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline-7,9-diol
Codeine
C₁₈H₂₁NO₃ · PubChem 5284371 →
(4R,4aR,7S,7aR,12bS)-9-methoxy-3-methyl-2,4,4a,7,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-ol
Thebaine
C₁₉H₂₁NO₃ · PubChem 5324289 →
(4R,7aR,12bS)-7,9-dimethoxy-3-methyl-2,4,7a,13-tetrahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline
Noscapine
C₂₂H₂₃NO₇ · PubChem 275196 →
(3S)-6,7-dimethoxy-3-[(5R)-4-methoxy-6-methyl-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-3H-2-benzofuran-1-one
Tropane alkaloids
1 plant — Brugmansia suaveolens
Scopolamine
C₁₇H₂₁NO₄
Hyoscine · epoxide-bearing tropane ester
L-Hyoscyamine
C₁₇H₂₃NO₃
Natural levorotatory tropane ester
Atropine
C₁₇H₂₃NO₃
Racemic hyoscyamine
Minor alkaloids
Littorine · tropine · pseudotropine · apoatropine
Organ- and environment-dependent biosynthetic intermediates
Psilocybin
1 plant — Psilocybe (P. aztecorum, P. caerulescens, P. cubensis, P. mexicana, P. zapotecorum)
Psilocybin
C₁₂H₁₇N₂O₄P · PubChem 10624 →
[3-[2-(dimethylamino)ethyl]-1H-indol-4-yl] dihydrogen phosphate
Baeocystin
C₁₁H₁₅N₂O₄P · PubChem 161359 →
[3-[2-(methylamino)ethyl]-1H-indol-4-yl] dihydrogen phosphate
Isoxazoles (muscimol)
1 plant — Amanita muscaria
minor
photoproduct
photoproduct
Muscazone
C₅H₆N₂O₃
Ultraviolet degradation product related to ibotenic acid
Sesquiterpene lactones
1 plant — Calea zacatechichi
GERM
LACTONE
LACTONE
Calein A
Germacranolide sesquiterpene lactone
A major bitter constituent reported from infusions and organic extracts
GERM
LACTONE
LACTONE
Calein C
Germacranolide sesquiterpene lactone
One of several caleins with variable acyl substitution
Acacetin
C₁₆H₁₂O₅
5,7-dihydroxy-4′-methoxyflavone
Chlorogenic acid
C₁₆H₁₈O₉
5-O-caffeoylquinic acid
Quinolizidine alkaloids
1 plant — Heimia salicifolia
Vertine
also called cryogenine
Biphenylquinolizidine lactone · the most studied Heimia alkaloid
Lythrine
Biphenylquinolizidine lactone
Diuretic in animal studies
Lyfoline
Biphenylquinolizidine lactone
With epi-lyfoline
Nesodine
Quinolizidine alkaloid
One of the four most studied