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.^[1] Similar to other trace amines, tryptamine binds to human trace amine-associated receptor 1 (TAAR1) as an agonist.^[2]

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 Ann and Alexander Shulgin under the title TiHKAL ("Tryptamines I Have Known and Loved").

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.^[3]

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

Pharmacology

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-T)

List of substituted tryptamines

Table

Compound	RN1	RN2	R4	R5	Rα	Structure
AMT (Indopan)	H	H	H	H	CH3
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
Psilocin (4-HO-DMT)	CH3	CH3	OH	H	H
4-HO-MiPT (Miprocin)	CH3	CH(CH3)2	OH	H	H
Psilocybin (4-PO-DMT)	CH3	CH3	OP(OH)2=O	H	H
Bufotenin (5-HO-DMT)	CH3	CH3	H	OH	H
5-MeO-DMT	CH3	CH3	H	OCH3	H
5-MeO-DALT	CH2CH=CH2	CH2CH=CH2	H	OCH3	H
5-MeO-DiPT	CH(CH3)2	CH(CH3)2	H	OCH3	H
5-MeO-MiPT	CH3	CH(CH3)2	H	OCH3	H
MiPT	CH3	CH(CH3)2	H	H	H
DiPT	CH(CH3)2	CH(CH3)2	H	H	H
NMT	CH3	H	H	H	H
DMT	CH3	CH3	H	H	H
MET	CH2CH3	CH3	H	H	H
MPT	CH2CH2CH3	CH3	H	H	H
EPT	CH2CH2CH3	CH2CH3	H	H	H
DPT	CH2CH2CH3	CH2CH2CH3	H	H	H
Ibogaine	CH2CH2(CH2-)CH2-	CH2(CH-CH3)CH--	H	OCH3	H

See also

• Responsible use
• Lysergamide
• TiHKAL
• Entheogen
• Phenethylamine

External links

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

References