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Tryptamine (compound)

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Revision as of 23:35, 15 October 2019 by >Tracer (Added melatonin and 5-HTP in List of substituted tryptamines)
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Substitutive structure of a tryptamine molecule

Tryptamine is a monoamine alkaloid found in animals, plants and fungi.[citation needed] It contains an indole ring structure, and is structurally similar to the amino acid tryptophan, from which the name derives.[citation needed] 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 Anne and Alexander Shulgin under the title TiHKAL ("Tryptamines I Have Known and Loved") in 1997.[citation needed]

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

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

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
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

References

  1. ↑ Jones R.S. (1982). "Tryptamine: a neuromodulator or neurotransmitter in mammalian brain?". Progress in neurobiology. 19 (1–2): 117–139. https://doi.org/10.1016/0301-0082(82)90023-5
  2. ↑ Khan MZ, Nawaz W (October 2016). "The emerging roles of human trace amines and human trace amine-associated receptors (hTAARs) in central nervous system". Biomed. Pharmacother. 83: 439–449. doi:10.1016/j.biopha.2016.07.002. PMID 27424325.
  3. ↑ "Tryptamine: a neuromodulator or neurotransmitter in mammalian brain?" | doi:10.1016/0301-0082(82)90023-5
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