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.

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

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	R^α	R^4	R^5	R^N1	R^N2	Full Name
	Tryptamine	Natural	H	H	H	H	H	3-(2-aminoethyl)indole / 2-(1H-indol-3-yl)ethanamine
	Bufotenin	Natural	H	H	OH	CH3	CH3	5-hydroxy-N,N-dimethyltryptamine
	Nω-Methylserotonin (norbufotenin)	Natural	H	H	OH	CH3	H	5-hydroxy-N-methyltryptamine
	Serotonin	Natural	H	H	OH	H	H	5-hydroxytryptamine
	DMT	Natural	H	H	H	CH3	CH3	N,N-dimethyltryptamine
	Melatonin	Natural	H	H	OCH3	O=C-CH3	H	5-methoxy-N-acetyltryptamine
	N-Acetylserotonin	Natural	H	H	OH	O=C-CH3	H	5-hydroxy-N-acetyltryptamine
	5-Bromo-DMT	Natural	H	H	Br	CH3	CH3	5-bromo-N,N-dimethyltryptamine
	5-MeO-DMT	Natural	H	H	OCH3	CH3	CH3	5-methoxy-N,N-dimethyltryptamine
	5-MeO-NMT	Natural	H	H	OCH3	CH3	H	5-methoxy-N-methyltryptamine
	NMT	Natural	H	H	H	H	CH3	N-methyltryptamine
	Norbaeocystin	Natural	H	OPO3H2	H	H	H	4-phosphoryloxy-tryptamine
	Baeocystin	Natural	H	OPO3H2	H	CH3	H	4-phosphoryloxy-N-methyl-tryptamine
	Psilocybin	Natural	H	PO4	H	CH3	CH3	4-phosphoryloxy-N,N-dimethyltryptamine
	Psilocin	Natural	H	OH	H	CH3	CH3	4-hydroxy-N,N-dimethyltryptamine
	Tryptophan	Natural	COOH	H	H	H	H	α-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-DMT	artificial	H	H	OCH2CH3	CH3	CH3	5-ethoxy-N,N-dimethyltryptamine
	5-Ethyl-DMT	artificial	H	H	CH2CH3	CH3	CH3	5-ethyl-N,N-dimethyltryptamine
	5-Fluoro-DMT	artificial	H	H	F	CH3	CH3	5-fluoro-N,N-dimethyltryptamine
	5-Methyl-DMT (5,N,N-TMT)	artificial	H	H	CH3	CH3	CH3	5,N,N-trimethyltryptamine
	5-(Nonyloxy)tryptamine	artificial	H	H	O(CH2)8CH3	H	H	5-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	R^α	R^4	R^5	R^N1	R^N2	Full Name

See also

• Table of naturally occurring tryptamines
• Ergoline
• TiHKAL
• Substituted phenethylamine
• Substituted amphetamine
• Substituted methylenedioxyphenethylamine
• 2C, DOx, 25-NB

References