Substituted tryptamine

Substituted tryptamines, or 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 are found in fungi, plants and animals; and sometimes used by humans for the neurological or psychotropic effects of the substance. Prominent examples of tryptamine alkaloids include psilocybin (from "Psilocybin mushrooms") and DMT. In South America, dimethyltryptamine is obtained from numerous plant sources, like chacruna, and it is often used in ayahuasca brews. Many synthetic tryptamines have also been made, including the migraine drug sumatriptan, 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

Substituted alpha-alkyltryptamines also comprise a large class and are listed separately.

Selected tryptamines
Chemical structure Short Name Origin Rα R4 R5 RN1 RN2 Full Name
TryptamineNaturalHHHHH3-(2-aminoethyl)indole / 2-(1H-indol-3-yl)ethanamine
BufoteninNaturalHHOHCH3CH35-hydroxy-N,N-dimethyltryptamine
Nω-Methylserotonin (norbufotenin)NaturalHHOHCH3H5-hydroxy-N-methyltryptamine
SerotoninNaturalHHOHHH5-hydroxytryptamine
DMTNaturalHHHCH3CH3N,N-dimethyltryptamine
MelatoninNaturalHHOCH3O=C-CH3H5-methoxy-N-acetyltryptamine
N-AcetylserotoninNaturalHHOHO=C-CH3H5-hydroxy-N-acetyltryptamine
5-Bromo-DMTNaturalHHBrCH3CH35-bromo-N,N-dimethyltryptamine
5-MeO-DMTNaturalHHOCH3CH3CH35-methoxy-N,N-dimethyltryptamine
5-MeO-NMTNaturalHHOCH3CH3H5-methoxy-N-methyltryptamine
NMTNaturalHHHHCH3N-methyltryptamine
NorbaeocystinNaturalHOPO3H2HHH4-phosphoryloxy-tryptamine
BaeocystinNaturalHOPO3H2HCH3H4-phosphoryloxy-N-methyl-tryptamine
PsilocybinNaturalHPO4HCH3CH34-phosphoryloxy-N,N-dimethyltryptamine
PsilocinNaturalHOHHCH3CH34-hydroxy-N,N-dimethyltryptamine
TryptophanNaturalCOOHHHHHα-carboxyltryptamine
DET artificial H H H CH2CH3 CH2CH3 N,N-diethyltryptamine
DPT artificial H H H CH2CH2CH3 CH2CH2CH3 N,N-dipropyltryptamine
DiPT artificial H H H CH(CH3)2 CH(CH3)2 N,N-diisopropyltryptamine
DALT artificial H H H H2C=CH-CH2 H2C=CH-CH2 N,N-diallyltryptamine
5-MeO-DALT artificial H H OCH3 H2C=CH-CH2 H2C=CH-CH2 5-methoxy-N,N-diallyltryptamine
5-MeO-MALT artificial H H OCH3 H2C=CH-CH2 CH3 5-methoxy-N-Methyl-N-allyltryptamine
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
5-MT-NBOMe artificial H H OCH3 H CH2C6H4(o-OCH3) 5-methoxy-N-(ortho-methoxybenzyl)tryptamine
5-BT artificial H H OCH2C6H5 H H 5-Benzyloxytryptamine
5-CT artificial H H CONH2 H H 5-Carboxamidotryptamine
5-Ethoxy-DMTartificialHHOCH2CH3CH3CH35-ethoxy-N,N-dimethyltryptamine
5-Ethyl-DMTartificialHHCH2CH3CH3CH35-ethyl-N,N-dimethyltryptamine
5-Fluoro-DMTartificialHHFCH3CH35-fluoro-N,N-dimethyltryptamine
5-Methyl-DMT (5,N,N-TMT)artificialHHCH3CH3CH35,N,N-trimethyltryptamine
5-(Nonyloxy)tryptamineartificialHHO(CH2)8CH3HH5-nonyloxytryptamine
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-EPT artificial H OH H CH2CH3 CH2CH2CH3 4-hydroxy-N-ethyl-N-propyltryptamine
4-HO-MPT artificial H OH H CH3 CH2CH2CH3 4-hydroxy-N-methyl-N-propyltryptamine
4-HO-MiPT artificial H OH H CH(CH3)2 CH3 4-hydroxy-N-isopropyl-N-methyltryptamine
4-HO-McPT artificial H OH H C3H5 CH3 4-hydroxy-N-cyclopropyl-N-methyltryptamine
4-HO-McPeT artificial H OH H C5H9 CH3 4-hydroxy-N-cyclopentyl-N-methyltryptamine
4-HO-DPT artificial H OH H CH2CH2CH3 CH2CH2CH3 4-hydroxy-N,N-dipropyltryptamine
4-HO-DIPT artificial H OH H CH(CH3)2 CH(CH3)2 4-hydroxy-N,N-diisopropyltryptamine
4-HO-DSBT artificial H OH H CH(CH3)CH2CH3 CH(CH3)CH2CH3 4-hydroxy-N,N-disecbutyltryptamine
Zolmitriptan artificial H H -(CHNHC=OOCH2) CH3 CH3 5-( 4-(S)-1,3-oxazolidin-2-one)-N,N-dimethyltryptamine
Chemical Structure Short Name Origin Rα R4 R5 RN1 RN2 Full Name

See also

References

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