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 group via an ethyl sidechain. In substituted tryptamines, the indole ring, sidechain, and/or amino group are modified by substituting another group for one of the hydrogen 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 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

s also comprise a large class and are listed separately.
Chemical structureShort NameOriginRαR4R5RN1RN2Full Name
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TryptamineNaturalHHHHH3-indole / 2-ethanamine
BufoteninNaturalHHOHCH3CH35-hydroxy-N,N-dimethyltryptamine
Nω-Methylserotonin 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
DETartificialHHHCH2CH3CH2CH3N,N-diethyltryptamine
DPTartificialHHHCH2CH2CH3CH2CH2CH3N,N-dipropyltryptamine
DiPTartificialHHHCH2CH2N,N-diisopropyltryptamine
DALTartificialHHHH2C=CH-CH2H2C=CH-CH2N,N-diallyltryptamine
5-MeO-DALTartificialHHOCH3H2C=CH-CH2H2C=CH-CH25-methoxy-N,N-diallyltryptamine
5-MeO-MALTartificialHHOCH3H2C=CH-CH2CH35-methoxy-N-Methyl-N-allyltryptamine
5-MeO-DIPTartificialHHOCH3CH2CH25-methoxy-N,N-diisopropyltryptamine
5-MeO-MiPTartificialHHOCH3CH3CH25-methoxy-N,N-methylisopropyltryptamine
5-MT-NBOMeartificialHHOCH3HCH2C6H45-methoxy-N-tryptamine
5-BTartificialHHOCH2C6H5HH5-Benzyloxytryptamine
5-CTartificialHHCONH2HH5-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 artificialHHCH3CH3CH35,N,N-trimethyltryptamine
5-tryptamineartificialHHO8CH3HH5-nonyloxytryptamine
4-HO-DETartificialHOHHCH2CH3CH2CH34-hydroxy-N,N-diethyltryptamine
4-AcO-DMTartificialHOCOCH3HCH3CH34-acetoxy-N,N-dimethyltryptamine
4-HO-METartificialHOHHCH3CH2CH34-hydroxy-N-methyl-N-ethyltryptamine
4-HO-EPTartificialHOHHCH2CH3CH2CH2CH34-hydroxy-N-ethyl-N-propyltryptamine
4-HO-MPTartificialHOHHCH3CH2CH2CH34-hydroxy-N-methyl-N-propyltryptamine
4-HO-MiPTartificialHOHHCH2CH34-hydroxy-N-isopropyl-N-methyltryptamine
4-HO-McPTartificialHOHHC3H5CH34-hydroxy-N-cyclopropyl-N-methyltryptamine
4-HO-McPeTartificialHOHHC5H9CH34-hydroxy-N-cyclopentyl-N-methyltryptamine
4-HO-DPTartificialHOHHCH2CH2CH3CH2CH2CH34-hydroxy-N,N-dipropyltryptamine
4-HO-DIPTartificialHOHHCH2CH24-hydroxy-N,N-diisopropyltryptamine
4-HO-DSBTartificialHOHHCHCH2CH3CHCH2CH34-hydroxy-N,N-disecbutyltryptamine
ZolmitriptanartificialHH-CH3CH35--N,N-dimethyltryptamine
Chemical StructureShort NameOriginRαR4R5RN1RN2Full Name