Tryptamine

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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

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 (Procin) 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
NMT CH3 H H H [[ ]]
DPT CH2CH2CH3 CH2CH2CH3 H H H DPT.svg
Ibogaine CH2CH2(CH2-)CH2- CH2(CH-CH3)CH-- H OCH3 H Ibogaine.svg

See also

External links

References

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  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