Substituted tryptamines

For the eponymous compound, see Tryptamine (compound).

Substitutive structure of a tryptamine molecule

Substituted tryptamines (or simply tryptamines) are a group of organic compounds that are based upon the tryptamine core structure. The class is composed of all the derivative compounds which can be formed by substituting one or more hydrogen atoms in the tryptamine core structure with other substituents. Natural tryptamines are found in most plants and animals, forming from the decarboxylation of the amino acid tryptophan.

The chemical class encompasses a variety of biologically important compounds such as hormones like melatonin and the neurotransmitter serotonin (5-hydroxytryptamine). Many psychoactive tryptamines have been found to occur in nature, although a large number of synthetic variants have been discovered in recent years. Notably, the dimethyltryptamine (DMT) and 5-MeO-DMT have been found to occur in the human body, although their function is unclear. Most of the known substituted tryptamines act as psychedelics (e.g. psilocybin, DMT, ibogaine), although there are some that have entactogenic properties (e.g. aMT, 5-MeO-MiPT). Lysergamides can technically be classified as complex tryptamines, like Ibogaine.

In terms of subjective effects, psychedelic tryptamines are generally regarded as producing a significantly stronger and "deeper" psychedelic effect than the other major class of psychedelics, the substituted phenethylamines (e.g. mescaline or the 2C-x family). Users tend to report greater amounts of ego dissolution, time distortion, conceptual thinking, and transpersonal effects such as unity and interconnectedness with substituted tryptamines. The reason for this is unknown. The subcategory of hallucinogens known as entheogens predominantly consist of tryptamines such as DMT (including ayahuasca), 5-MeO-DMT, and psilocybin.

A systematic investigation of 55 psychoactive tryptamine and lysergamide compounds was published by Ann and Alexander Shulgin under the title TiHKAL ("Tryptamines I Have Known and Loved") in 1997.

Chemistry

The tryptamine core structure consists of an indole ring with attached amino group via a two-carbon sidechain (monoamine chain) at R₃. Ring unsubstituted tryptamines, or so called "base tryptamines", can have various substitutions at the nitrogen (R_N1 and R_N2) and at R_α. Ring substituted tryptamines can be further substituted at the R₄ and R₅ positions on the indole ring.

Pharmacology

Further information: Serotonergic psychedelic

The psychedelic effects of tryptamines are believed to come from their efficacy at the 5-HT_2A receptor as a partial agonist. However, the role of these interactions and how they result in the psychedelic experience is the subject of on-going research.

List of substituted tryptamines

This table does not include the following groups of substituted tryptamines:

• Lysergamides

Ring-unsubstituted tryptamines

Sometimes referred to as "unsubstituted tryptamines" or "base tryptamines"

Compound	Common name	RN1	RN2	R4	R5	Rα	Structure
Tryptamine	Tryptamine	H	H	H	H	H
NMT	NMT	CH3	H	H	H	H
DMT	Dimethyltryptamine, Dmitri, "The Spirit Molecule"	CH3	CH3	H	H	H
MET	Methylethyltryptamine	CH2CH3	CH3	H	H	H
DET	Diethyltryptamine	CH2CH3	CH2CH3	H	H	H
MPT	Methylpropyltryptamine	CH2CH2CH3	CH3	H	H	H
MiPT	Methylisopropyltryptamine	CH3	CH(CH3)2	H	H	H
EPT	Ethylpropyltryptamine	CH2CH2CH3	CH2CH3	H	H	H
DiPT	Diisopropyltryptamine	CH(CH3)2	CH(CH3)2	H	H	H
DPT	Dipropyltryptamine	CH2CH2CH3	CH2CH2CH3	H	H	H
AMT	alpha-methyltryptamine, Indopan	H	H	H	H	CH3

Ring substituted tryptamines

Compound	Common name	RN1	RN2	R2	R4	R5	R6	Rα	Rβ	Structure
4-AcO-DiPT	Ipracetin	CH(CH3)2	CH(CH3)2	H	OC(O)CH3	H	H	H	H
4-AcO-DMT	Psilacetin	CH3	CH3	H	OC(O)CH3	H	H	H	H
4-AcO-MET	Metacetin	CH2CH3	CH3	H	OC(O)CH3	H	H	H	H
4-AcO-DET	Ethacetin	CH2CH3	CH2CH3	H	OC(O)CH3	H	H	H	H
4-AcO-MiPT	Mipracetin	CH3	CH(CH3)2	H	OC(O)CH3	H	H	H	H
4-HO-DET	Ethocin	CH2CH3	CH2CH3	H	OH	H	H	H	H
4-HO-EPT	Eprocin	CH2CH2CH3	CH2CH3	H	OH	H	H	H	H
4-HO-DPT	Procin	CH2CH2CH3	CH2CH2CH3	H	OH	H	H	H	H
4-HO-MET	Metocin	CH2CH3	CH3	H	OH	H	H	H	H
4-HO-MPT	Meprocin	CH2CH2CH3	CH3	H	OH	H	H	H	H
4-HO-DMT	Psilocin	CH3	CH3	H	OH	H	H	H	H
4-HO-MiPT	Miprocin	CH3	CH(CH3)2	H	OH	H	H	H	H
4-PO-DMT	Psilocybin	CH3	CH3	H	OP(OH)2=O	H	H	H	H
Serotonin		H	H	H	H	OH	H	H	H
5-HO-DMT	Bufotenin	CH3	CH3	H	H	OH	H	H	H
5-MeO-DMT		CH3	CH3	H	H	OCH3	H	H	H
5-MeO-DET		CH2CH3	CH2CH3	H	H	OCH3	H	H	H
5-MeO-DPT	Foxtrot	CH2CH2CH3	CH2CH2CH3	H	H	OCH3	H	H	H
5-MeO-DALT	Foxtrot	CH2CH=CH2	CH2CH=CH2	H	H	OCH3	H	H	H
5-MeO-DiPT	Foxy	CH(CH3)2	CH(CH3)2	H	H	OCH3	H	H	H
5-MeO-MiPT	Moxy	CH3	CH(CH3)2	H	H	OCH3	H	H	H
Ibogaine		CH2CH2(CH2-)CH2-	CH2(CH-CH3)CH--	-	H	OCH3	H	H	H
5-HTP		H	H	H	H	OH	H	CO2H	H
Melatonin		COCH3	H	H	H	OCH3	H	H	H
TIK-301		COCH3	H	H	H	OCH3	Cl	H	CH3
Pericine		CH2C(CHCH3)-	CH2CH2-	C(CH2)-	H	H	H	H	H
Carbazocine		CH2C3H5	CH2CH2-	-	H	H	H	CH-(CH2CH2CH2CH2-)	H

See also

• Tryptamine
• Responsible use
• Lysergamide
• TiHKAL
• Entheogen
• Phenethylamine

External links

• Substituted tryptamine (Wikipedia)
• List of naturally occurring tryptamines (Wikipedia)