Tryptamine

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Substitutive structure of a tryptamine molecule

Tryptamine is a monoamine alkaloid found in animals, plants and fungi.

Substituted tryptamine refers to a class of compounds which are typically capable of producing strong psychedelic and entheogenic effects.

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.[1]

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-HT2A 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:

List of substituted tryptamines

Table

Compound RN1 RN2 R4 R5 Rα Structure
AMT (Indopan) H H H H CH3 ΑMT.svg
4-AcO-DiPT (Ipracetin) CH(CH3)2 CH(CH3)2 OC(O)CH3 H H 4-AcO-DiPT.svg
4-AcO-DMT (Psilacetin) CH3 CH3 OC(O)CH3 H H 4-AcO-DMT.svg
4-AcO-MET (Metacetin) CH3 CH2CH3 OC(O)CH3 H H 4-AcO-MET.svg
4-HO-DET (Ethocin) CH2CH3 CH2CH3 OH H H 4-HO-DET.svg
4-HO-DPT (Psiprocin) CH2CH2CH3 CH2CH2CH3 OH H H 4-HO-DPT.svg
4-HO-MET (Metocin) CH3 CH2CH3 OH H H 4-HO-MET.svg
Psilocin (4-HO-DMT) CH3 CH3 OH H H Psilocin.svg
4-HO-MiPT (Miprocin) CH3 CH(CH3)2 OH H H 4-HO-MiPT.svg
Psilocybin (4-PO-DMT) CH3 CH3 OP(OH)2=O H H Psilocybin.svg
Bufotenin (5-HO-DMT) CH3 CH3 H OH H Bufotenin.svg
5-MeO-DMT CH3 CH3 H OCH3 H 5-MeO-DMT.svg
5-MeO-DALT CH2CH=CH2 CH2CH=CH2 H OCH3 H 5-MeO-DALT.svg
5-MeO-DiPT CH(CH3)2 CH(CH3)2 H OCH3 H 5-MeO-DiPT.svg
5-MeO-MiPT CH3 CH(CH3)2 H OCH3 H 5-MeO-MiPT.svg
DiPT CH(CH3)2 CH(CH3)2 H H H DiPT.svg
DMT CH3 CH3 H H H DMT.svg
DPT CH2CH2CH3 CH2CH2CH3 H H H DPT.svg
Ibogaine CH2CH2(CH2-)CH2- CH2(CH-CH3)CH-- H OCH3 H Ibogaine.svg

See also

References

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  1. "Tryptamine: a neuromodulator or neurotransmitter in mammalian brain?" | doi:10.1016/0301-0082(82)90023-5