Substituted tryptamine

The structure of substituted tryptamines. Tryptamine itself is obtained when R4=R5=RN1=RN2=Rα = H.

Substituted tryptamines, or simply tryptamines, also conceptualizable as serotonin analogues, are organic compounds which may be thought of as being derived from tryptamine itself. The molecular structures of all tryptamines contain an indole ring, joined to an amino (NH2) group via an ethyl (−CH2–CH2−) sidechain. In substituted tryptamines, the indole ring, sidechain, and/or amino group are modified by substituting another group for one of the hydrogen (H) atoms.

Well-known tryptamines include serotonin, an important neurotransmitter, and melatonin, a hormone involved in regulating the sleep-wake cycle. Tryptamine alkaloids found in fungi, plants and animals are sometimes used by humans and other animals, notably, the jaguar,[1] for their psychotropic effects. Prominent examples of tryptamine alkaloids include psilocybin (from "Psilocybin mushrooms") and DMT (from numerous plant sources, e.g. chacruna, often used in ayahuasca brews). Many synthetic tryptamines have also been made, including the migraine drug sumatriptan and its relatives, and psychedelic drugs.

The tryptamine structure, in particular its indole ring, may be part of the structure of some more complex compounds, for example: LSD, ibogaine, mitragynine and yohimbine. A thorough investigation of dozens of tryptamine compounds was published by Ann and Alexander Shulgin under the title TiHKAL.

List of substituted tryptamines

 Selected tryptamines
Short Name Origin Rα R4 R5 RN1 RN2 Full Name
TryptamineNatural H H H H H 3-(2-aminoethyl)indole / 2-(1H-indol-3-yl)ethanamine
BufoteninNatural H H OH CH3 CH3 5-hydroxy-N,N-dimethyltryptamine
Nω-Methylserotonin (norbufotenin)Natural H H OH CH3 H 5-hydroxy-N-methyltryptamine
SerotoninNatural H H OH H H 5-hydroxytryptamine
DMTNatural H H H CH3 CH3 N,N-dimethyltryptamine
MelatoninNatural H H OCH3 O=C-CH3 H 5-methoxy-N-acetyltryptamine
N-AcetylserotoninNatural H H OH O=C-CH3 H 5-hydroxy-N-acetyltryptamine
5-Bromo-DMTNatural H H Br CH3 CH3 5-bromo-N,N-dimethyltryptamine
5-MeO-DMTNatural H H OCH3 CH3 CH3 5-methoxy-N,N-dimethyltryptamine
5-MeO-NMTNatural H H OCH3 CH3 H 5-methoxy-N-methyltryptamine
NMTNatural H H H H CH3 N-methyltryptamine
NorbaeocystinNatural H OPO3H2 H H H 4-phosphoryloxy-tryptamine
BaeocystinNatural H OPO3H2 H CH3 H 4-phosphoryloxy-N-methyl-tryptamine
PsilocybinNatural H PO4 H CH3 CH3 4-phosphoryloxy-N,N-dimethyltryptamine
PsilocinNatural H OH H CH3 CH3 4-hydroxy-N,N-dimethyltryptamine
TryptophanNatural COOH H H H H α-carboxyltryptamine
αET artificial CH2CH3 H H H H α-ethyltryptamine
αMT artificial CH3 H H H H α-methyltryptamine
DALT artificial H H H H2C=CH-CH2 H2C=CH-CH2 N,N-diallyltryptamine
DET artificial H H H CH2CH3 CH2CH3 N,N-diethyltryptamine
DiPT artificial H H H CH(CH3)2 CH(CH3)2 N,N-diisopropyltryptamine
DPT artificial H H H CH2CH2CH3 CH2CH2CH3 N,N-dipropyltryptamine
5-MeO-αMT artificial CH3 H OCH3 H H 5-methoxy-α-methyltryptamine
5-MeO-DALT artificial H H OCH3 H2C=CH-CH2 H2C=CH-CH2 5-methoxy-N,N-diallyltryptamine
4-HO-DET artificial H OH H CH2CH3 CH2CH3 4-hydroxy-N,N-diethyltryptamine
4-AcO-DMT artificial H OCOCH3 H CH3 CH3 4-acetoxy-N,N-dimethyltryptamine
4-HO-MET artificial H OH H CH3 CH2CH3 4-hydroxy-N-methyl-N-ethyltryptamine
4-HO-DIPT artificial H OH H CH(CH3)2 CH(CH3)2 4-hydroxy-N,N-diisopropyltryptamine
5-MeO-DIPT artificial H H OCH3 CH(CH3)2 CH(CH3)2 5-methoxy-N,N-diisopropyltryptamine
5-MeO-MiPT artificial H H OCH3 CH3 CH(CH3)2 5-methoxy-N,N-methylisopropyltryptamine
4-HO-MiPT artificial H OH H CH(CH3)2 CH3 4-hydroxy-N-isopropyl-N-methyltryptamine
Sumatriptan artificial H H CH2SO2NHCH3 CH3 CH3 5-(methylaminosulfonylmethylene)-N,N-dimethyltryptamine
Zolmitriptan artificial H H -(CHNHC=OOCH2) CH3 CH3 5-( 4-(S)-1,3-oxazolidin-2-one)-N,N-dimethyltryptamine
Short Name Origin Rα R4 R5 RN1 RN2 Full Name

See also

References

  1. ↑ Robin Rodd (2011). "Reassessing the Cultural and Psychopharmacological Significance of Banisteriopsis caapi: Preparation, Classification and Use Among the Piaroa of Southern Venezuela". Journal of Psychoactive Drugs 40 (3): 301–307. doi:10.1080/02791072.2008.10400645.
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