Substituted tryptamine

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 or other animals, such as the jaguar,^[1] 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

Selected tryptamines

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
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	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 and DOx

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.