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. A 2022 study has found the variety of tryptamines present in wild mushrooms may affect the therapeutic impact.^[1]

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

This list is incomplete; you can help by adding missing items. (October 2021)

Zdroj:https://en.wikipedia.org?pojem=Substituted_alpha-alkyltryptamine
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Selected tryptamines

Chemical structure	Short Name	Origin	Ring Substitution	RN1	RN2	Full Name	CAS Number
	Tryptamine	Animals, plants, fungi	H	H	H	3-(2-aminoethyl)indole / 2-(1H-indol-3-yl)ethanamine	61-54-1
	NMT	Plants	H	H	CH3	N-methyltryptamine	61-49-4
	2-HO-NMT	Plants	2-OH	H	CH3	2-hydroxy-N-methyltryptamine	106987-89-7
	5-MeO-NMT	Plants	5-OCH3	H	CH3	5-methoxy-N-methyltryptamine	2009-03-2
	Serotonin	Animals, plants	5-OH	H	H	5-hydroxytryptamine	50-67-9
	Nω-Methylserotonin (norbufotenin)	Plants	5-OH	H	CH3	5-hydroxy-N-methyltryptamine	1134-01-6
	Bufotenin	Animals, plants, fungi	5-OH	CH3	CH3	5-hydroxy-N,N-dimethyltryptamine	487-93-4
	Bufotenidine	Amphibians	5-O−	(CH3)3		3--1H-indol-5-olate	487-91-2
	Melatonin	Animals, plants, microbes	5-OCH3	H	O=C-CH3	5-methoxy-N-acetyltryptamine	73-31-4
	N-Acetylserotonin	Animals	5-OH	H	O=C-CH3	5-hydroxy-N-acetyltryptamine	1210-83-9
	6-Hydroxymelatonin	Animals	5-OCH3, 6-OH	H	O=C-CH3	N-acetamide	2208-41-5
	4-HO-NMT	Fungi	4-OH	H	CH3	4-hydroxy-N-methyltryptamine	28363-70-4
	Psilocin	Fungi	4-OH	CH3	CH3	4-hydroxy-N,N-dimethyltryptamine	520-53-6
	Norbaeocystin	Fungi	4-OPO3H2	H	H	4-phosphoryloxy-tryptamine	21420-59-7
	Baeocystin	Fungi	4-OPO3H2	H	CH3	4-phosphoryloxy-N-methyl-tryptamine	21420-58-6
	Psilocybin	Fungi	4-OPO3H2	CH3	CH3	4-phosphoryloxy-N,N-dimethyltryptamine	520-52-5
	Aeruginascin	Fungi	4-OPO3H2	(CH3)3		2-(trimethylazaniumyl)ethyl-1H-indol-4-yl hydrogen phosphate	114264-95-8
	DMT	Animals, plants	H	CH3	CH3	N,N-dimethyltryptamine	61-50-7
	Lespedamine	Plants	1-OCH3	CH3	CH3	1-methoxy-N,N-dimethyltryptamine	4335-93-7
	5-MeO-DMT	Animals, plants	5-OCH3	CH3	CH3	5-methoxy-N,N-dimethyltryptamine	1019-45-0
	5-Bromo-DMT	Marine sponges, invertebrates	5-Br	CH3	CH3	5-bromo-N,N-dimethyltryptamine	17274-65-6
	6-Bromotryptamine	Marine invertebrates	6-Br	H	H	6-bromotryptamine	96624-18-9
	5,6-Dibromotryptamine	Marine invertebrates	5,6-Br	H	H	5,6-dibromotryptamine
	5,6-Dibromo-NMT	Marine invertebrates	5,6-Br	H	CH3	5,6-dibromo-N-methyltryptamine
	5,6-Dibromo-DMT	Marine sponges, invertebrates	5,6-Br	CH3	CH3	5,6-dibromo-N,N-dimethyltryptamine	72853-80-6
	Desformylflustrabromine	Marine invertebrates	2-(α,α-dimethylallyl), 6-Br	H	CH3	2-6-bromo-2-(2-methylbut-3-en-2-yl)-1H-indol-3-yl-N-methylethanamine	474657-72-2
	Convolutindole A	Marine invertebrates	2,4,6-Br, 1,7-OCH3	CH3	CH3	1,7-dimethoxy-2,4,6-tribromo-N,N-dimethyltryptamine	443356-86-3
	Acetryptine	artificial	5-COCH3	H	H	5-Acetyltryptamine	3551-18-6
	5-BT	artificial	5-OCH2C6H5	H	H	5-Benzyloxytryptamine	20776-45-8
	5-CT	artificial	5-CONH2	H	H	5-Carboxamidotryptamine	74885-09-9
	5-(Nonyloxy)tryptamine	artificial	5-O(CH2)8CH3	H	H	5-nonyloxytryptamine	157798-12-4
	2-Methyl-5-hydroxytryptamine	artificial	2-CH3, 5-OH	H	H	3-(2-aminoethyl)-2-methyl-1H-indol-5-ol	78263-90-8
	NET	artificial	H	H	CH2CH3	N-ethyltryptamine	61-53-0
	NiPT	artificial	H	H	CH(CH3)2	N-isopropyltryptamine	14121-10-9
	NcPT	artificial	H	H	C3H5	N-cyclopropyltryptamine
	NSBT	artificial	H	H	CH(CH3)CH2CH3	N-sec-butyltryptamine
	NTBT	artificial	H	H	C(CH3)3	N-2-(1H-indol-3-yl)ethyl-2-methylpropan-2-amine
	5-MeO-T-NBOMe	artificial	5-OCH3	H	CH2C6H4(o-OCH3)	5-methoxy-N-(ortho-methoxybenzyl)tryptamine	1335331-37-7
	5-MT-NB3OMe [2]	artificial	5-OCH3	H	CH2C6H4(m-OCH3)	5-methoxy-N-(meta-methoxybenzyl)tryptamine	1648553-42-7
	5-MeO-NBpBrT	artificial	5-OCH3	H	CH2C6H4(p-Br)	N-(4-Bromobenzyl)-2-(5-methoxy-1H-indol-3-yl)ethanamine	155639-13-7
	5-MeO-34MPEMT [3]	artificial	5-OCH3	CH3	CH2CH2C6H3(p,m-OCH3)	N-methyl-N-2-(3,4-dimethoxyphenyl)ethyl-2-(5-methoxy-1H-indol-3-yl)ethanamine
	Idalopirdine	artificial	6-F	H	CH2C6H4(m-OCH2CF2CF2H)	2-(6-Fluoro-1H-indol-3-yl)-N-(3-(2,2,3,3-tetrafluoropropoxy)benzyl)ethanamine	467459-31-0
	Z2876442907[4]	artificial	4-CH3	H	CH2(C3HNS)COOCH2CH3	ethyl 2-({2-(4-methyl-1H-indol-3-yl)ethylamino}methyl)-1,3-thiazole-5-carboxylate
	Pyr-T	artificial	H	(CH2)4		3-2-(Pyrrolidin-1-yl)ethyl-1H-indole	14008-96-9
	4-HO-pyr-T	artificial	4-OH	(CH2)4		3-2-(Pyrrolidin-1-yl)ethyl-1H-indol-4-ol	63097-26-7
	5-MeO-pyr-T	artificial	5-OCH3	(CH2)4		5-Methoxy-3-2-(pyrrolidin-1-yl)ethyl-1H-indole	3949-14-2
	Indolylethylfentanyl	artificial	H	(CH2)5-4-N(COCH2CH3)C6H5		N-1-2-(1H-indol-3-yl)ethylpiperidin-4-yl-N-phenylpropanamide	58399-46-5
	MET	artificial	H	CH3	CH2CH3	N-Methyl-N-ethyltryptamine	5599-69-9
	MPT	artificial	H	CH3	CH2CH2CH3	N-Methyl-N-propyltryptamine	850032-72-3
	MiPT	artificial	H	CH3	CH(CH3)2	N-Methyl-N-isopropyltryptamine	96096-52-5
	McPT	artificial	H	CH3	C3H5	N-Methyl-N-cyclopropyltryptamine	1373918-63-8
	EcPT	artificial	H	CH2CH3	C3H5	N-ethyl-N-cyclopropyltryptamine
	PcPT	artificial	H	CH2CH2CH3	C3H5	N-propyl-N-cyclopropyltryptamine
	iPcPT	artificial	H	CH(CH3)2	C3H5	N-isopropyl-N-cyclopropyltryptamine
	DcPT	artificial	H	C3H5	C3H5	N,N-dicyclopropyltryptamine	1373918-62-7
	MBT	artificial	H	CH3	(CH2)3CH3	N-Methyl-N-butyltryptamine	848130-12-1
	MSBT	artificial	H	CH3	CH(CH3)CH2CH3	N-Methyl-N-sec-butyltryptamine
	MiBT	artificial	H	CH3	CH2CH(CH3)2	N-Methyl-N-iso-butyltryptamine
	McPMT	artificial	H	CH3	CH2C3H5	N-Methyl-N-(cyclopropylmethyl)tryptamine
	DET	artificial	H	CH2CH3	CH2CH3	N,N-diethyltryptamine	61-51-8
	EPT	artificial	H	CH2CH3	CH2CH2CH3	N-Ethyl-N-propyltryptamine	850032-68-7
	EiPT	artificial	H	CH2CH3	CH(CH3)2	N-Ethyl-N-isopropyltryptamine	848130-11-0