Substituted tryptamines

For the eponymous compound, see Tryptamine.

Substitutive structure of a tryptamine molecule

Substituted tryptamines (also referred to as tryptamines) are a group of organic compounds that are based upon the tryptamine 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). 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).

In terms of subjective effects, substituted 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). The subcategory of hallucinogens known as entheogens predominantly consist of substituted tryptamines such as DMT (including ayahuasca), 5-MeO-DMT and psilocybin.

A systematic investigation of dozens of psychoactive tryptamine 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.

List of substituted tryptamines

Ring unsubstituted tryptamines

Sometimes referred to as "base tryptamines".

Compound	Common name	RN1	RN2	R4	R5	Rα	Structure
NMT		CH3	H	H	H	H
DMT		CH3	CH3	H	H	H
MET		CH2CH3	CH3	H	H	H
DET		CH2CH3	CH2CH3	H	H	H
MPT		CH2CH2CH3	CH3	H	H	H
MiPT		CH3	CH(CH3)2	H	H	H
EPT		CH2CH2CH3	CH2CH3	H	H	H
DiPT		CH(CH3)2	CH(CH3)2	H	H	H
DPT		CH2CH2CH3	CH2CH2CH3	H	H	H
AMT		H	H	H	H	CH3

Ring substituted tryptamines

Compound	Common name	RN1	RN2	R4	R5	Rα	Structure
4-AcO-DiPT	Ipracetin	CH(CH3)2	CH(CH3)2	OC(O)CH3	H	H
4-AcO-DMT	Psilacetin	CH3	CH3	OC(O)CH3	H	H
4-AcO-MET	Metacetin	CH2CH3	CH3	OC(O)CH3	H	H
4-AcO-DET	Psilacetin	CH2CH3	CH2CH3	OC(O)CH3	H	H
4-AcO-MiPT	Mipracetin	CH3	CH(CH3)2	OC(O)CH3	H	H
4-HO-DET	Ethacetin	CH2CH3	CH2CH3	OH	H	H
4-HO-DPT	Procin	CH2CH2CH3	CH2CH2CH3	OH	H	H
4-HO-MET	Metocin	CH2CH3	CH3	OH	H	H
4-HO-MPT	Meprocin	CH2CH2CH3	CH3	OH	H	H
4-HO-DMT	Psilocin	CH3	CH3	OH	H	H
4-HO-MiPT	Miprocin	CH3	CH(CH3)2	OH	H	H
4-PO-DMT	Psilocybin	CH3	CH3	OP(OH)2=O	H	H
Serotonin		H	H	H	OH	H
5-HO-DMT	Bufotenin	CH3	CH3	H	OH	H
5-MeO-DMT		CH3	CH3	H	OCH3	H
5-MeO-DET		CH2CH3	CH2CH3	H	OCH3	H
5-MeO-DPT		CH2CH2CH3	CH2CH2CH3	H	OCH3	H
5-MeO-DALT		CH2CH=CH2	CH2CH=CH2	H	OCH3	H
5-MeO-DiPT	Foxy	CH(CH3)2	CH(CH3)2	H	OCH3	H
5-MeO-MiPT	Moxy	CH3	CH(CH3)2	H	OCH3	H
Ibogaine		CH2CH2(CH2-)CH2-	CH2(CH-CH3)CH--	H	OCH3	H
Melatonin		H	COCH3	H	OCH3	H
5-HTP		H	H	H	OH	CO2H

See also

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

External links

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