Substituted tryptamine

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

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[edit]

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
Tryptamine structure.svg Tryptamine Natural H H H H H 3-(2-aminoethyl)indole / 2-(1H-indol-3-yl)ethanamine
Bufotenin2DACS.svg Bufotenin Natural H H OH CH3 CH3 5-hydroxy-N,N-dimethyltryptamine
Norbufotenine.svg Nω-Methylserotonin (norbufotenin) Natural H H OH CH3 H 5-hydroxy-N-methyltryptamine
Serotonin-2D-skeletal.svg Serotonin Natural H H OH H H 5-hydroxytryptamine
DMT.svg DMT Natural H H H CH3 CH3 N,N-dimethyltryptamine
Melatonin.svg Melatonin Natural H H OCH3 O=C-CH3 H 5-methoxy-N-acetyltryptamine
N-Acetylserotonin.png N-Acetylserotonin Natural H H OH O=C-CH3 H 5-hydroxy-N-acetyltryptamine
5-Bromo-DMT.svg 5-Bromo-DMT Natural H H Br CH3 CH3 5-bromo-N,N-dimethyltryptamine
5-MeO-DMT.svg 5-MeO-DMT Natural H H OCH3 CH3 CH3 5-methoxy-N,N-dimethyltryptamine
5-MeO-NMT.png 5-MeO-NMT Natural H H OCH3 CH3 H 5-methoxy-N-methyltryptamine
Methyltryptamine.png NMT Natural H H H H CH3 N-methyltryptamine
Norbaeocystin.png Norbaeocystin Natural H OPO3H2 H H H 4-phosphoryloxy-tryptamine
Baeocystin Formula V.1.svg Baeocystin Natural H OPO3H2 H CH3 H 4-phosphoryloxy-N-methyl-tryptamine
Psilocybn.svg Psilocybin Natural H PO4 H CH3 CH3 4-phosphoryloxy-N,N-dimethyltryptamine
Psilocin.svg Psilocin Natural H OH H CH3 CH3 4-hydroxy-N,N-dimethyltryptamine
L-Tryptophan - L-Tryptophan.svg Tryptophan Natural COOH H H H H α-carboxyltryptamine
Diethyltryptamine.svg DET artificial H H H CH2CH3 CH2CH3 N,N-diethyltryptamine
DPT.svg DPT artificial H H H CH2CH2CH3 CH2CH2CH3 N,N-dipropyltryptamine
DiPT.svg DiPT artificial H H H CH(CH3)2 CH(CH3)2 N,N-diisopropyltryptamine
DALT-structure.png DALT artificial H H H H2C=CH-CH2 H2C=CH-CH2 N,N-diallyltryptamine
5-MeO-DALT.svg 5-MeO-DALT artificial H H OCH3 H2C=CH-CH2 H2C=CH-CH2 5-methoxy-N,N-diallyltryptamine
5-MeO-MALT.png 5-MeO-MALT artificial H H OCH3 H2C=CH-CH2 CH3 5-methoxy-N-Methyl-N-allyltryptamine
5-MeO-DiPT.svg 5-MeO-DIPT artificial H H OCH3 CH(CH3)2 CH(CH3)2 5-methoxy-N,N-diisopropyltryptamine
5-MeO-MiPT.svg 5-MeO-MiPT artificial H H OCH3 CH3 CH(CH3)2 5-methoxy-N,N-methylisopropyltryptamine
5MT-NBOMe structure.png 5-MT-NBOMe artificial H H OCH3 H CH2C6H4(o-OCH3) 5-methoxy-N-(ortho-methoxybenzyl)tryptamine
5-benzyloxytryptamine.png 5-BT artificial H H OCH2C6H5 H H 5-Benzyloxytryptamine
5-Carboxamidotryptamine.svg 5-CT artificial H H CONH2 H H 5-Carboxamidotryptamine
5-EtO-DMT structure.png 5-Ethoxy-DMT artificial H H OCH2CH3 CH3 CH3 5-ethoxy-N,N-dimethyltryptamine
5-Ethyl-DMT structure.svg 5-Ethyl-DMT artificial H H CH2CH3 CH3 CH3 5-ethyl-N,N-dimethyltryptamine
5-Fluoro-DMT structure.png 5-Fluoro-DMT artificial H H F CH3 CH3 5-fluoro-N,N-dimethyltryptamine
5,N,N-TMT.svg 5-Methyl-DMT (5,N,N-TMT) artificial H H CH3 CH3 CH3 5,N,N-trimethyltryptamine
5-Nonyloxytryptamine structure.png 5-(Nonyloxy)tryptamine artificial H H O(CH2)8CH3 H H 5-nonyloxytryptamine
4-HO-DET.svg 4-HO-DET artificial H OH H CH2CH3 CH2CH3 4-hydroxy-N,N-diethyltryptamine
O-Acetylpsilocin chemical structure.png 4-AcO-DMT artificial H OCOCH3 H CH3 CH3 4-acetoxy-N,N-dimethyltryptamine
4-HO-MET.svg 4-HO-MET artificial H OH H CH3 CH2CH3 4-hydroxy-N-methyl-N-ethyltryptamine
4-Hydroxy-N-ethyl-N-propyltryptamine.svg 4-HO-EPT artificial H OH H CH2CH3 CH2CH2CH3 4-hydroxy-N-ethyl-N-propyltryptamine
4-HO-MPT.png 4-HO-MPT artificial H OH H CH3 CH2CH2CH3 4-hydroxy-N-methyl-N-propyltryptamine
Miprocin.png 4-HO-MiPT artificial H OH H CH(CH3)2 CH3 4-hydroxy-N-isopropyl-N-methyltryptamine
4-HO-McPT structure.png 4-HO-McPT artificial H OH H C3H5 CH3 4-hydroxy-N-cyclopropyl-N-methyltryptamine
4-HO-McPeT structure.png 4-HO-McPeT artificial H OH H C5H9 CH3 4-hydroxy-N-cyclopentyl-N-methyltryptamine
4-HO-DPT.png 4-HO-DPT artificial H OH H CH2CH2CH3 CH2CH2CH3 4-hydroxy-N,N-dipropyltryptamine
4-HO-DIPT.SVG 4-HO-DIPT artificial H OH H CH(CH3)2 CH(CH3)2 4-hydroxy-N,N-diisopropyltryptamine
4-HO-DSBT.png 4-HO-DSBT artificial H OH H CH(CH3)CH2CH3 CH(CH3)CH2CH3 4-hydroxy-N,N-disecbutyltryptamine
Zolmitriptan Structure V.1.svg 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[edit]