Substituted tryptamines

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For the eponymous compound, see Tryptamine (compound).
Substitutive structure of a tryptamine molecule

Substituted tryptamines (or simply tryptamines) are a group of organic compounds that are based upon the tryptamine core structure. The class is composed of all the derivative compounds which can be formed by substituting one or more hydrogen atoms in the tryptamine core structure with other substituents. Natural tryptamines are found in most plants and animals, forming from the decarboxylation of the amino acid tryptophan.[1]

The chemical class encompasses a variety of biologically important compounds such as hormones like melatonin and the neurotransmitter serotonin (5-hydroxytryptamine). Many psychoactive tryptamines have been found to occur in nature, although a large number of synthetic variants have been discovered in recent years. Notably, the dimethyltryptamine (DMT) and 5-MeO-DMT have been found to occur in the human body, although their function is unclear.[citation needed] Most of the known substituted tryptamines act as psychedelics (e.g. psilocybin, DMT, ibogaine), although there are some that have entactogenic properties (e.g. aMT, 5-MeO-MiPT).

In terms of subjective effects, psychedelic tryptamines are generally regarded as producing a significantly stronger and "deeper" psychedelic effect than the other major class of psychedelics, the substituted phenethylamines (e.g. mescaline or the 2C-x family). Users tend to report greater amounts of ego dissolution, time distortion, conceptual thinking, and transpersonal effects such as unity and interconnectedness with substituted tryptamines. The reason for this is unknown. The subcategory of hallucinogens known as entheogens predominantly consist of tryptamines such as DMT (including ayahuasca), 5-MeO-DMT, and psilocybin.

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

Chemistry

The tryptamine core structure consists of an indole ring with attached amino group via a two-carbon sidechain (monoamine chain) at R3. Ring unsubstituted tryptamines, or so called "base tryptamines", can have various substitutions at the nitrogen (RN1 and RN2) and at Rα. Ring substituted tryptamines can be further substituted at the R4 and R5 positions on the indole ring.

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 is the subject of on-going research.

List of substituted tryptamines

Ring unsubstituted tryptamines

Sometimes referred to as "base tryptamines".

Compound Common name RN1 RN2 R4 R5 Rα Structure
NMT CH3 H H H H NMT.svg
DMT Dimethyltryptamine, "Dmitri", "The Spirit Molecule" CH3 CH3 H H H DMT.svg
MET Methylethyltryptamine CH2CH3 CH3 H H H MET.svg
DET Diethyltryptamine CH2CH3 CH2CH3 H H H DET.svg
MPT Methylpropyltryptamine CH2CH2CH3 CH3 H H H MPT.svg
MiPT Methylisopropyltryptamine CH3 CH(CH3)2 H H H MiPT.svg
EPT Ethylpropyltryptamine CH2CH2CH3 CH2CH3 H H H EPT.svg
DiPT Diisopropyltryptamine CH(CH3)2 CH(CH3)2 H H H DiPT.svg
DPT Dipropyltryptamine CH2CH2CH3 CH2CH2CH3 H H H DPT.svg
AMT alpha-methyltryptamine, Indopan H H H H CH3 ΑMT.svg

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-DiPT.svg
4-AcO-DMT Psilacetin CH3 CH3 OC(O)CH3 H H 4-AcO-DMT.svg
4-AcO-MET Metacetin CH2CH3 CH3 OC(O)CH3 H H 4-AcO-MET.svg
4-AcO-DET Ethacetin CH2CH3 CH2CH3 OC(O)CH3 H H 4-AcO-DET.svg
4-AcO-MiPT Mipracetin CH3 CH(CH3)2 OC(O)CH3 H H 4-AcO-MiPT.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 CH2CH3 CH3 OH H H 4-HO-MET.svg
4-HO-MPT Meprocin CH2CH2CH3 CH3 OH H H 4-HO-MPT.svg
4-HO-DMT Psilocin CH3 CH3 OH H H Psilocin.svg
4-HO-MiPT Miprocin CH3 CH(CH3)2 OH H H 4-HO-MiPT.svg
4-PO-DMT Psilocybin CH3 CH3 OP(OH)2=O H H Psilocybin.svg
Serotonin H H H OH H Serotonin.svg
5-HO-DMT Bufotenin CH3 CH3 H OH H Bufotenin.svg
5-MeO-DMT CH3 CH3 H OCH3 H 5-MeO-DMT.svg
5-MeO-DET CH2CH3 CH2CH3 H OCH3 H 5-MeO-DET.svg
5-MeO-DPT CH2CH2CH3 CH2CH2CH3 H OCH3 H 5-MeO-DPT.svg
5-MeO-DALT CH2CH=CH2 CH2CH=CH2 H OCH3 H 5-MeO-DALT.svg
5-MeO-DiPT Foxy CH(CH3)2 CH(CH3)2 H OCH3 H 5-MeO-DiPT.svg
5-MeO-MiPT Moxy CH3 CH(CH3)2 H OCH3 H 5-MeO-MiPT.svg
Ibogaine CH2CH2(CH2-)CH2- CH2(CH-CH3)CH-- H OCH3 H Ibogaine.svg
Melatonin H COCH3 H OCH3 H Melatonin.svg
5-HTP H H H OH CO2H 5-HTP.svg

See also

External links

References

  1. "Tryptamines". ScienceDirect. Archived from the original on January 11, 2020. Retrieved January 11, 2020.