Pharmakon Compounds

Compounds

The chemistry axis of the archive

The same archive read chemically: 16 compound families across 22 plants. A shared molecule is a real historical connector, but chemistry never exhausts the rite: each family links back to the living traditions that carry it.

Tryptamine

5 plants — Anadenanthera colubrina · Anadenanthera peregrina · Diplopterys cabrerana · Mimosa tenuiflora · Psychotria viridis

Bufotenine

C₁₂H₁₆N₂O · PubChem 10257 →

3-[2-(dimethylamino)ethyl]-1H-indol-5-ol

Trace historical report · detected in some modern brews, botanical source unresolved

N,N-Dimethyltryptamine

C₁₂H₁₆N₂ · PubChem 6089 →

2-(1H-indol-3-yl)-N,N-dimethylethanamine

Principal documented psychoactive alkaloid · 5-HT_2A agonist

5-Methoxy-DMT

C₁₃H₁₈N₂O · PubChem 1832 →

2-(5-methoxy-1H-indol-3-yl)-N,N-dimethylethanamine

Trace older report · not established as a regular constituent of traditional yagé

Other constituents

Indole N-oxides · bufotenidine · tannins · flavonoids

Strongly tissue-dependent chemistry

Bark ethnomedicine cannot be inferred from seed alkaloids

Related indoles

N-oxides · N-methyltryptamines · serotonin derivatives

Tissue- and specimen-dependent

Analytically relevant; contribution to the whole preparation unresolved

N-Methyltryptamine

C₁₁H₁₄N₂ · PubChem 6088 →

N-methyl-2-(1H-indol-3-yl)ethanamine

Minor alkaloid and probable biosynthetic intermediate

Maoi

2 plants — Banisteriopsis caapi · Peganum harmala

Harmine

C₁₃H₁₂N₂O · PubChem 5280953 →

7-methoxy-1-methyl-9H-pyrido[3,4-b]indole

Principal β-carboline · reversible MAO-A inhibitor

Tetrahydroharmine

C₁₃H₁₆N₂O · PubChem 159809 →

2,3,4,9-tetrahydro-7-methoxy-1-methyl-1H-pyrido[3,4-b]indole

Weak MAO-A inhibition · serotonin-reuptake effects in vitro

Harmaline

C₁₃H₁₄N₂O · PubChem 3564 →

7-methoxy-1-methyl-3,4-dihydro-β-carboline

Reversible MAO-A inhibitor · tremorogenic at high exposure

N,N-Dimethyltryptamine

C₁₂H₁₆N₂ · PubChem 6089 →

2-(1H-indol-3-yl)-N,N-dimethylethanamine

Companion-plant alkaloid · not a principal caapi-stem constituent

Mescaline

2 plants — Echinopsis pachanoi · Lophophora williamsii

Mescaline

C₁₁H₁₇NO₃ · PubChem 4076 →

2-(3,4,5-trimethoxyphenyl)ethanamine

Principal psychedelic phenethylamine · 5-HT_2A-mediated

3-Methoxytyramine

C₉H₁₃NO₂

4-(2-aminoethyl)-2-methoxyphenol

Minor reported phenethylamine · not established as a visionary driver

Hordenine

C₁₀H₁₅NO · PubChem 68313 →

4-[2-(dimethylamino)ethyl]phenol

Minor phenethylamine · not established as a psychedelic at peyote levels

VARIABLE
ALKALOID
FIELD

Other reported alkaloids

3,4-dimethoxyphenethylamine · tyramine · hydroxy-dimethoxyphenethylamines · anhalonidine/anhalinine

Presence and abundance depend on specimen and method.

Do not infer a reproducible “entourage effect” from detection alone

Pellotine

C₁₃H₁₉NO₃ · PubChem 65742 →

6,7-dimethoxy-1,2-dimethyl-1,2,3,4-tetrahydroisoquinolin-8-ol

Tetrahydroisoquinoline · historically investigated as a sedative

Anhalonidine

C₁₂H₁₇NO₃ · PubChem 87201 →

N-desmethylpellotine

Minor tetrahydroisoquinoline alkaloid

Sesquiterpene

1 plant — Calea zacatechichi

GERM
LACTONE

Calein A

Germacranolide sesquiterpene lactone

A major bitter constituent reported from infusions and organic extracts

Biological activity demonstrated preclinically · oneirogenic role unproven

GERM
LACTONE

Calein C

Germacranolide sesquiterpene lactone

One of several caleins with variable acyl substitution

Metabolic and antiparasitic studies · CNS mechanism unresolved

Acacetin

C₁₆H₁₂O₅

5,7-dihydroxy-4′-methoxyflavone

Flavone detected in aqueous extracts · broad preclinical pharmacology

Chlorogenic acid

C₁₆H₁₈O₉

5-O-caffeoylquinic acid

Phenolic acid in infusions · not specific to Calea

Ibogaine

1 plant — Tabernanthe iboga

Ibogaine

C₂₀H₂₆N₂O

12-methoxyibogamine

Principal studied iboga alkaloid · long-acting polypharmacology

Ibogamine

C₁₉H₂₄N₂

Parent iboga alkaloid scaffold

Root-bark constituent · biological contribution incompletely resolved

Tabernanthine

C₂₀H₂₆N₂O

Methoxyibogamine positional isomer

Named from Tabernanthe · one component of whole-root chemistry

Voacangine

C₂₂H₂₈N₂O₃

Carbomethoxy-methoxy iboga alkaloid

Biosynthetic relative and semisynthetic ibogaine precursor

Salvinorin

1 plant — Salvia divinorum

Salvinorin A

C₂₃H₂₈O₈

Trans-neoclerodane diterpenoid

Principal psychoactive constituent · potent selective KOR agonist

Salvinorin B

C₂₁H₂₆O₇ · CAS 92545-30-7

Deacetylated salvinorin

Plant constituent and major inactive/weakly active metabolite of salvinorin A

Salvinorin C

C₂₅H₃₀O₉

Minor diacetylated neoclerodane

Much lower KOR affinity than salvinorin A

Salvinorins D–J

Neoclerodane series

With divinatorins and salvinicins

Chemotaxonomic and biosynthetic field · no established equivalent psychoactivity

Psilocybin

1 plant — Psilocybe cubensis

Opiates

1 plant — Papaver somniferum

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.

Lsa

1 plant — Ipomoea corymbosa

Ergine · LSA

C₁₆H₁₇N₃O

D-lysergic acid amide · lysergamide

Serotonergic, adrenergic and dopaminergic receptor ligand

Lysergic acid α-hydroxyethylamide

C₁₈H₂₁N₃O₂

LAH / LSH · N-(1-hydroxyethyl)lysergamide

Labile principal alkaloid in some fresh chemotypes

Ergometrine · ergonovine

C₁₉H₂₃N₃O₂

Lysergic acid propanolamide

Mixed serotonin/adrenergic activity · uterotonic pharmacology

Chanoclavine-I

C₁₆H₂₀N₂O

Tricyclic clavine alkaloid

Biosynthetic precursor within fungal ergot-alkaloid pathways

Cocaine

1 plant — Erythroxylum coca

Cocaine

C₁₇H₂₁NO₄

Benzoylmethylecgonine · tropane ester

Monoamine-transporter inhibitor · voltage-gated sodium-channel blocker

Cinnamoylcocaine

C₁₉H₂₃NO₄

Methylecgonine cinnamate · geometric isomers occur

Characteristic minor-to-major coca alkaloid · content varies by lineage

Tropacocaine

C₁₅H₁₉NO₂

Benzoyltropine · tropane ester

Local-anaesthetic alkaloid · usually minor

Hygrine

C₈H₁₅NO

N-methylpyrrolidinyl ketone

Volatile pyrrolidine alkaloid · biosynthetic and forensic marker

Ergot alkaloids

1 plant — Claviceps purpurea

Ergotamine

C₃₃H₃₅N₅O₅

Ergopeptine · lysergic acid–tripeptide cyclol

Persistent vasoconstrictor · historic migraine drug

Ergometrine / ergonovine

C₁₉H₂₃N₃O₂

Simple lysergic acid amide

Uterotonic · central activity at sufficient exposure

Ergocristine

C₃₅H₃₉N₅O₅

Ergopeptine alkaloid

Major in some chemotypes · regulated analytical congener

Ergine / LSA

C₁₆H₁₇N₃O

Lysergic acid amide

Usually minor in raw sclerotia · central to processed-kykeon hypothesis

Mitragynine

1 plant — Mitragyna speciosa

Mitragynine

C₂₃H₃₀N₂O₄

Major corynanthe-type monoterpenoid indole alkaloid

Atypical partial μ-opioid agonism · adrenergic and serotonergic actions

7-Hydroxymitragynine · 7-OH

C₂₃H₃₀N₂O₅

Oxidised minor alkaloid and active mitragynine metabolite

Higher-affinity, higher-efficacy μ-opioid partial agonist

Speciociliatine

C₂₃H₃₀N₂O₄

C-3 epimer of mitragynine

μ-opioid partial agonism · high systemic exposure in animal studies

Paynantheine

C₂₃H₂₈N₂O₄

Corynanthe-type indole alkaloid

5-HT₁A activity · smooth-muscle and polyreceptor effects under study

Isoxazole

1 plant — Amanita muscaria

Muscimol

C₄H₆N₂O₂ · PubChem 4266 →

5-(aminomethyl)-1,2-oxazol-3-ol

Orthosteric GABA_A-receptor agonist · principal centrally active isoxazole

Ibotenic acid

C₅H₆N₂O₄ · PubChem 1233 →

(S)-2-amino-2-(3-hydroxy-5-isoxazolyl)acetic acid

NMDA and metabotropic-glutamate agonist · biosynthetic precursor of muscimol

Muscarine

C₉H₂₀NO₂⁺ · PubChem 9308 →

Quaternary ammonium muscarinic acetylcholine-receptor agonist

Trace constituent · historically misidentified as the main intoxicant

minor
photoproduct

Muscazone

C₅H₆N₂O₃

Ultraviolet degradation product related to ibotenic acid

Minor and incompletely characterised contribution

Tropane

1 plant — Brugmansia suaveolens

Scopolamine

C₁₇H₂₁NO₄

Hyoscine · epoxide-bearing tropane ester

Central and peripheral muscarinic antagonist · commonly prominent

L-Hyoscyamine

C₁₇H₂₃NO₃

Natural levorotatory tropane ester

Muscarinic antagonist · racemises to atropine

Atropine

C₁₇H₂₃NO₃

Racemic hyoscyamine

Clinical antimuscarinic and analytical reference compound

Minor alkaloids

Littorine · tropine · pseudotropine · apoatropine

Organ- and environment-dependent biosynthetic intermediates

Chemotaxonomic profile remains incompletely sampled

Theobromine

1 plant — Theobroma cacao

Theobromine

C₇H₈N₄O₂ · PubChem 5429 →

3,7-dimethylpurine-2,6-dione

Principal cacao methylxanthine · adenosine-receptor antagonist

Caffeine

C₈H₁₀N₄O₂ · PubChem 2519 →

1,3,7-trimethylpurine-2,6-dione

Lower concentration; stronger central stimulant per unit mass

(−)-Epicatechin

C₁₅H₁₄O₆ · PubChem 72276 →

Flavan-3-ol and procyanidin building block

Vascular and metabolic research; not an entheogen

Anandamide

C₂₂H₃₇NO₂ · PubChem 5281969 →

N-arachidonoylethanolamine

Trace detection in chocolate; ritual significance unestablished