Tryptamine

Substitutive structure of a tryptamine molecule

Tryptamine is a monoamine alkaloid found in animals, plants and fungi. It contains an indole ring structure, and is structurally similar to the amino acid tryptophan, from which the name derives. Tryptamine is found in trace amounts in the brains of mammals and is hypothesized to play a role as a neuromodulator or neurotransmitter. Similar to other trace amines, tryptamine binds to human trace amine-associated receptor 1 (TAAR1) as an agonist.

Tryptamine is the common functional group in a set of compounds collectively termed "substituted tryptamines." Pharmacologically, substituted tryptamines are best known for being able to produce psychedelic and entheogenic effects.

An investigation of dozens of psychoactive tryptamine compounds was published by Anne and Alexander Shulgin under the title TiHKAL ("Tryptamines I Have Known and Loved") in 1997.

Chemistry

The tryptamine molecule is an indole alkaloid comprised of an indole ring attached to a monoamine (single nitrogen group-containing) chain. It is a derivative of the amino acid tryptophan and is found in trace amounts in the brains of mammals, where it is hypothesized to play a role as a neuromodulator or neurotransmitter.

Hydrogen atoms around the structure can be substituted for other functional groups to produce drugs of varying potency, affinity, efficacy and half-life.

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 continues to remain elusive.

Several neurotransmitters are derived from tryptamine, such as:

• Serotonin (5-Hydroxy-Tryptamine or 5-HT)
• Melatonin (5-MeO-N-Acetyl-Tryptamine)

List of substituted tryptamines

Ring unsubstituted tryptamines

Note: 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	CH3	CH2CH3	OC(O)CH3	H	H
4-HO-DET	Ethocin	CH2CH3	CH2CH3	OH	H	H
4-HO-DPT	Procin	CH2CH2CH3	CH2CH2CH3	OH	H	H
4-HO-MET	Metocin	CH3	CH2CH3	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

• Responsible use
• Lysergamide
• TiHKAL
• Entheogen
• Phenethylamine

External links

• Tryptamine (Wikipedia)
• List of naturally occurring tryptamines (Wikipedia)
• Tryptamine (TiHKAL / Isomer Design)