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 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

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-[2-(trimethylazaniumyl)ethyl]-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-[2-(6-Hydroxy-5-methoxy-1H-indol-3-yl)ethyl]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		[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)ethyl]amino}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)ethyl]piperidin-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
	DPT	artificial	H	CH2CH2CH3	CH2CH2CH3	N,N-dipropyltryptamine	61-52-9
	PiPT	artificial	H	CH2CH2CH3	CH(CH3)2	N-Propyl-N-isopropyltryptamine	1354632-00-0
	DiPT	artificial	H	CH(CH3)2	CH(CH3)2	N,N-diisopropyltryptamine	14780-24-6
	EBT	artificial	H	CH2CH3	(CH2)3CH3	N-ethyl-N-butyltryptamine
	PBT	artificial	H	CH2CH2CH3	(CH2)3CH3	N-propyl-N-butyltryptamine
	iPsBT	artificial	H	CH(CH3)2	CH(CH3)CH2CH3	N-isopropyl-N-sec-butyltryptamine
	DBT	artificial	H	(CH2)3CH3	(CH2)3CH3	N,N-dibutyltryptamine	15741-77-2
	DIBT	artificial	H	CH2CH(CH3)2	CH2CH(CH3)2	N,N-diisobutyltryptamine	63938-64-7
	DSBT	artificial	H	CH(CH3)CH2CH3	CH(CH3)CH2CH3	N,N-disecbutyltryptamine
	MALT	artificial	H	CH3	H2C=CH-CH2	N-methyl-N-allyltryptamine	1366416-29-6
	DALT	artificial	H	H2C=CH-CH2	H2C=CH-CH2	N,N-diallyltryptamine	60676-77-9
	ALiPT	artificial	H	H2C=CH-CH2	CH(CH3)2	N-allyl-N-isopropyltryptamine
	2-Methyl-DMT	artificial	2-CH3	CH3	CH3	(2-(2-methyl-1H-indol-3-yl)-1-methyl-ethyl)dimethylamine	1080-95-1
	2-Me-DET	artificial	2-CH3	CH2CH3	CH2CH3	N,N-Diethyl-2-(2-methyl-1H-indol-3-yl)ethan-1-amine	26628-88-6
	4-Amino-DMT [5]	artificial	4-NH2	CH3	CH3	4-amino-N,N-dimethyltryptamine	60331-61-5
	4-Methyl-DMT	artificial	4-CH3	CH3	CH3	4,N,N-trimethyltryptamine	28289-23-8
	4-MeO-DMT	artificial	4-OCH3	CH3	CH3	4-methoxy-N,N-dimethyltryptamine	3965-97-7
	4-MeO-MiPT	artificial	4-OCH3	CH3	CH(CH3)2	4-methoxy-N-methyl-N-isopropyltryptamine	96096-53-6
	4-MeO-DiPT	artificial	4-OCH3	CH(CH3)2	CH(CH3)2	4-methoxy-N,N-diisopropyltryptamine
	4-AcO-DMT	artificial	4-OCOCH3	CH3	CH3	4-acetoxy-N,N-dimethyltryptamine	92292-84-7
	4-PrO-DMT	artificial	4-OCOCH2CH3	CH3	CH3	4-propionyloxy-N,N-dimethyltryptamine	1373882-11-1
	4-HO-MET	artificial	4-OH	CH3	CH2CH3	4-hydroxy-N-methyl-N-ethyltryptamine	77872-41-4
	4-Acetoxy-MET	artificial	4-OCOCH3	CH3	CH2CH3	4-acetoxy-N-methyl-N-ethyltryptamine	1445751-40-5
	4-PO-MET	artificial	4-OPO3H2	CH3	CH2CH3	4-phosphoryloxy-N-methyl-N-ethyltryptamine
	4-HO-DET	artificial	4-OH	CH2CH3	CH2CH3	4-hydroxy-N,N-diethyltryptamine	22204-89-3
	4-Acetoxy-DET	artificial	4-OCOCH3	CH2CH3	CH2CH3	4-acetoxy-N,N-diethyltryptamine	1135424-15-5
	4-PO-DET	artificial	4-OPO3H2	CH2CH3	CH2CH3	4-phosphoryloxy-N,N-diethyltryptamine	60480-02-6
	4-HO-EPT	artificial	4-OH	CH2CH3	CH2CH2CH3	4-hydroxy-N-ethyl-N-propyltryptamine	2595431-59-5
	4-PO-EPT	artificial	4-OPO3H2	CH2CH3	CH2CH2CH3	4-phosphoryloxy-N-ethyl-N-propyltryptamine
	4-AcO-EiPT	artificial	4-OCOCH3	CH2CH3	CH(CH3)2	4-acetoxy-N-ethyl-N-isopropyltryptamine
	4-HO-MPT	artificial	4-OH	CH3	CH2CH2CH3	4-hydroxy-N-methyl-N-propyltryptamine	763035-03-6
	4-HO-MiPT	artificial	4-OH	CH(CH3)2	CH3	4-hydroxy-N-isopropyl-N-methyltryptamine	77872-43-6
	4-Acetoxy-MiPT	artificial	4-OCOCH3	CH3	CH(CH3)2	4-acetoxy-N-methyl-N-isopropyltryptamine	1024612-25-6
	4-HO-MALT [6]	artificial	4-OH	CH3	H2C=CH-CH2	4-hydroxy-N-Methyl-N-allyltryptamine
	4-AcO-MALT [7]	artificial	4-OCOCH3	CH3	H2C=CH-CH2	4-acetoxy-N-Methyl-N-allyltryptamine
	4-HO-NALT [8]	artificial	4-OH	H	H2C=CH-CH2	4-hydroxy-N-allyltryptamine
	4-HO-MSBT	artificial	4-OH	CH(CH3)CH2CH3	CH3	4-hydroxy-N-sec-butyl-N-methyltryptamine
	4-HO-EiBT	artificial [9]	4-OH	CH2CH(CH3)2	CH2CH3	4-hydroxy-N-iso-butyl-N-ethyltryptamine
	4-HO-McPT	artificial	4-OH	C3H5	CH3	4-hydroxy-N-cyclopropyl-N-methyltryptamine	2883663-05-4
	4-HO-McPeT	artificial	4-OH	C5H9	CH3	4-hydroxy-N-cyclopentyl-N-methyltryptamine	77872-48-1
	4-HO-McPMT [10]	artificial	4-OH	CH2C3H5	CH3	4-hydroxy-N-cyclopropylmethyl-N-methyltryptamine
	4-HO-DPT	artificial	4-OH	CH2CH2CH3	CH2CH2CH3	4-hydroxy-N,N-dipropyltryptamine	63065-88-3
	4-AcO-DPT	artificial	4-OCOCH3	CH2CH2CH3	CH2CH2CH3	4-acetoxy-N,N-dipropyltryptamine	1445751-75-6
	4-HO-PiPT	artificial	4-OH	CH2CH2CH3	CH(CH3)2	4-hydroxy-N-propyl-N-isopropyltryptamine
	4-AcO-PiPT	artificial	4-OCOCH3	CH2CH2CH3	CH(CH3)2	4-acetoxy-N-propyl-N-isopropyltryptamine
	4-HO-DIPT	artificial	4-OH	CH(CH3)2	CH(CH3)2	4-hydroxy-N,N-diisopropyltryptamine	132328-45-1
	4-Acetoxy-DiPT	artificial	4-OCOCH3	CH(CH3)2	CH(CH3)2	4-acetoxy-N,N-diisopropyltryptamine	936015-60-0
	4-PrO-DiPT	artificial	4-OCOCH2CH3	CH(CH3)2	CH(CH3)2	4-propionyloxy-N,N-diisopropyltryptamine	1373882-13-3
	FT-104	artificial	4-OCO(CH2)3COOH	CH(CH3)2	CH(CH3)2	4-glutaryloxy-N,N-diisopropyltryptamine
	4-PO-DiPT	artificial	4-OPO3H2	CH(CH3)2	CH(CH3)2	4-phosphoryloxy-N,N-diisopropyltryptamine	1373882-09-7
	4-HO-DALT	artificial	4-OH	H2C=CH-CH2	H2C=CH-CH2	4-hydroxy-N,N-diallyltryptamine
	4-AcO-DALT	artificial	4-OCOCH3	H2C=CH-CH2	H2C=CH-CH2	4-acetoxy-N,N-diallyltryptamine	1445751-71-2
	4-HO-DBT	artificial	4-OH	(CH2)3CH3	(CH2)3CH3	4-hydroxy-N,N-dibutyltryptamine	63065-89-4
	4-HO-DIBT	artificial	4-OH	CH2CH(CH3)2	CH2CH(CH3)2	4-hydroxy-N,N-diisobutyltryptamine
	4-HO-DSBT	artificial	4-OH	CH(CH3)CH2CH3	CH(CH3)CH2CH3	4-hydroxy-N,N-disecbutyltryptamine	127507-01-1
	5-MeO-MET	artificial	5-OCH3	CH2CH3	CH3	5-methoxy-N-Methyl-N-ethyltryptamine	16977-53-0
	5-MeO-DET	artificial	5-OCH3	CH2CH3	CH2CH3	5-methoxy-N,N-diethyltryptamine	2454-70-8
	5-MeO-MPT	artificial	5-OCH3	CH3	CH2CH2CH3	5-methoxy-N-methyl-N-propyltryptamine
	5-MeO-EPT	artificial	5-OCH3	CH2CH3	CH2CH2CH3	5-methoxy-N-ethyl-N-propyltryptamine	850032-67-6
	5-MeO-DPT	artificial	5-OCH3	CH2CH2CH3	CH2CH2CH3	5-methoxy-N,N-dipropyltryptamine	69496-75-9
	5-MeO-MALT	artificial	5-OCH3	H2C=CH-CH2	CH3	5-methoxy-N-Methyl-N-allyltryptamine	1373918-64-9
	5-MeO-DALT	artificial	5-OCH3	H2C=CH-CH2	H2C=CH-CH2	5-methoxy-N,N-diallyltryptamine	928822-98-4
	5-MeO-ALiPT	artificial	5-OCH3	H2C=CH-CH2	CH2CH(CH3)2	5-methoxy-N-allyl-N-isopropyltryptamine
	5-MeO-MiPT	artificial	5-OCH3	CH3	CH(CH3)2	5-methoxy-N,N-methylisopropyltryptamine	96096-55-8
	5,6-MeO-MiPT	artificial	5-OCH3, 6-OCH3	CH3	CH(CH3)2	5,6-dimethoxy-N,N-methylisopropyltryptamine
	5-MeO-McPT	artificial	5-OCH3	CH3	C3H5	5-methoxy-N-methyl-N-cyclopropyltryptamine
	5-MeO-McBT	artificial	5-OCH3	CH3	C4H7	5-methoxy-N-methyl-N-cyclobutyltryptamine
	5-MeO-EiPT	artificial	5-OCH3	CH2CH3	CH(CH3)2	5-methoxy-N-ethyl-N-isopropyltryptamine	850032-66-5
	5-MeO-PiPT	artificial	5-OCH3	CH2CH2CH3	CH(CH3)2	5-methoxy-N-propyl-N-isopropyltryptamine
	5-MeO-DIPT	artificial	5-OCH3	CH(CH3)2	CH(CH3)2	5-methoxy-N,N-diisopropyltryptamine	4021-34-5
	5-MeO-DBT	artificial	5-OCH3	(CH2)3CH3	(CH2)3CH3	5-methoxy-N,N-dibutyltryptamine	73785-42-9
	5-MeO-DSBT	artificial	5-OCH3	CH(CH3)CH2CH3	CH(CH3)CH2CH3	5-methoxy-N,N-di-sec-butyltryptamine
	5-MeS-DMT	artificial	5-SCH3	CH3	CH3	5-methylthio-N,N-dimethyltryptamine	5102-11-4
	5-AcO-DMT	artificial	5-OCOCH3	CH3	CH3	5-acetoxy-N,N-dimethyltryptamine	16977-50-7
	5-AcO-MET [11]	artificial	5-OCOCH3	CH3	CH2CH3	5-acetoxy-N-methyl-N-ethyltryptamine
	5-AcO-DET	artificial	5-OCOCH3	CH2CH3	CH2CH3	5-acetoxy-N,N-diethyltryptamine
	5-AcO-EPT [12]	artificial	5-OCOCH3	CH2CH3	CH2CH2CH3	5-acetoxy-N-ethyl-N-propyltryptamine
	5-AcO-DPT	artificial	5-OCOCH3	CH2CH2CH3	CH2CH2CH3	5-acetoxy-N,N-dipropyltryptamine
	5-AcO-MiPT	artificial	5-OCOCH3	CH3	CH(CH3)2	5-acetoxy-N-methyl-N-isopropyltryptamine
	5-AcO-DiPT	artificial	5-OCOCH3	CH(CH3)2	CH(CH3)2	5-acetoxy-N,N-diisopropyltryptamine
	5-Ethoxy-DMT	artificial	5-OCH2CH3	CH3	CH3	5-ethoxy-N,N-dimethyltryptamine	855245-09-9
	5-Ethoxy-MET	artificial	5-OCH2CH3	CH3	CH2CH3	5-ethoxy-N-methyl-N-ethyltryptamine
	5-Ethoxy-DET	artificial	5-OCH2CH3	CH2CH3	CH2CH3	5-ethoxy-N,N-diethyltryptamine
	5-Ethoxy-MPT	artificial	5-OCH2CH3	CH3	CH2CH2CH3	5-ethoxy-N-methyl-N-propyltryptamine
	5-Ethoxy-EPT	artificial	5-OCH2CH3	CH2CH3	CH2CH2CH3	5-ethoxy-N-ethyl-N-propyltryptamine
	5-Ethoxy-DPT	artificial	5-OCH2CH3	CH2CH2CH3	CH2CH3	5-ethoxy-N,N-dipropyltryptamine
	5-Ethoxy-MiPT	artificial	5-OCH2CH3	CH3	CH(CH3)2	5-ethoxy-N-methyl-N-isopropyltryptamine
	5-Ethoxy-EiPT	artificial	5-OCH2CH3	CH2CH3	CH(CH3)2	5-ethoxy-N-ethyl-N-isopropyltryptamine
	5-Ethoxy-DiPT	artificial	5-OCH2CH3	CH(CH3)2	CH(CH3)2	5-ethoxy-N,N-diisopropyltryptamine
	5-Ethoxy-DALT	artificial	5-OCH2CH3	H2C=CH-CH2	H2C=CH-CH2	5-ethoxy-N,N-diallyltryptamine
	5-BnO-DMT	artificial	5-OCH2C6H5	CH3	CH3	5-benzyloxy-N,N-dimethyltryptamine	101832-88-6
	5-HO-DET	artificial	5-OH	CH2CH3	CH2CH3	5-hydroxy-N,N-diethyltryptamine	14009-42-8
	5-HO-DPT	artificial	5-OH	CH2CH2CH3	CH2CH2CH3	5-hydroxy-N,N-dipropyltryptamine	36288-75-2
	5-HO-MiPT	artificial	5-OH	CH3	CH(CH3)2	5-hydroxy-N-methyl-N-isopropyltryptamine
	5-HO-DiPT	artificial	5-OH	CH(CH3)2	CH(CH3)2	5-hydroxy-N,N-diisopropyltryptamine	36288-76-3
	5-Methyl-DMT (5,N,N-TMT)	artificial	5-CH3	CH3	CH3	5,N,N-trimethyltryptamine	22120-39-4
	5-Ethyl-DMT	artificial	5-CH2CH3	CH3	CH3	5-ethyl-N,N-dimethyltryptamine	171783-25-8
	5-Isopropyl-DMT	artificial	5-CH(CH3)2	CH3	CH3	5-isopropyl-N,N-dimethyltryptamine	156281-04-8
	5-(t-Butyl)-DMT [13]	artificial	5-C(CH3)3	CH3	CH3	5-(tert-butyl)-N,N-dimethyltryptamine
	5-Fluoro-DMT	artificial	5-F	CH3	CH3	5-fluoro-N,N-dimethyltryptamine	22120-36-1
	5-Fluoro-MET	artificial	5-F	CH3	CH2CH3	5-fluoro-N-methyl-N-ethyltryptamine
	5-Fluoro-DET	artificial	5-F	CH2CH3	CH2CH3	5-fluoro-N,N-diethyltryptamine
	5-Fluoro-EPT	artificial	5-F	CH2CH3	CH2CH2CH3	5-fluoro-N-ethyl-N-propyltryptamine
	5-Fluoro-DPT	artificial	5-F	CH2CH2CH3	CH2CH2CH3	5-fluoro-N,N-dipropyltryptamine
	5-Fluoro-PiPT	artificial	5-F	CH2CH2CH3	CH(CH3)2	5-fluoro-N-propyl-N-isopropyltryptamine
	5-Fluoro-PcBT	artificial	5-F	CH2CH2CH3	CH(CH2)3	5-fluoro-N-propyl-N-cyclobutyltryptamine
	5-Fluoro-iPcBT	artificial	5-F	CH(CH3)2	CH(CH2)3	5-fluoro-N-isopropyl-N-cyclobutyltryptamine
	5-Fluoro-DiPT	artificial	5-F	CH(CH3)2	CH(CH3)2	5-fluoro-N,N-diisoproptryptamine
	5-Fluoro-sBALT	artificial	5-F	CH(CH3)CH2CH3	CH2CH=CH2	5-fluoro-N-sec-butyl-N-allyltryptamine
	5-Fluoro-M1MALT	artificial	5-F	CH3	CH(CH3)CH=CH2	5-fluoro-N-methyl-N-(1-methylallyl)tryptamine
	5-Chloro-DMT	artificial	5-Cl	CH3	CH3	5-chloro-N,N-dimethyltryptamine	22120-32-7
	5-Iodo-DMT	artificial	5-I	CH3	CH3	5-iodo-N,N-dimethyltryptamine	22120-38-3
	5-TFM-DMT	artificial	5-CF3	CH3	CH3	5-(trifluoromethyl)-N,N-dimethyltryptamine	2418713-32-1
	5-TFMO-DMT [14]	artificial	5-OCF3	CH3	CH3	5-(trifluoromethoxy)-N,N-dimethyltryptamine
	5-Nitro-DMT [15]	artificial	5-NO2	CH3	CH3	5-nitro-N,N-dimethyltryptamine	69937-13-9
	5-CN-DMT	artificial	5-C≡N	CH3	CH3	5-cyano-N,N-dimethyltryptamine	17380-42-6
	5-CN-DPT	artificial	5-C≡N	CH2CH2CH3	CH2CH2CH3	5-cyano-N,N-dipropyltryptamine	74885-19-1
	Almotriptan	artificial	5-(CH2SO2N(CH2)4)	CH3	CH3	N,N-dimethyl-2- [5-(pyrrolidin-1-ylsulfonylmethyl)- 1H-indol-3-yl]-ethanamine	154323-57-6
	Rizatriptan	artificial	5-(CH2(N3(CH)2))	CH3	CH3	N,N-dimethyl-2-[5-(1H-1,2,4-triazol-1-ylmethyl)-1H-indol-3-yl]ethanamine	145202-66-0
	Sumatriptan	artificial	5-(CH2SO2NHCH3)	CH3	CH3	1-[3-(2-Dimethylaminoethyl)-1H-indol-5-yl]-N-methyl-methanesulfonamide	103628-46-2
	Zolmitriptan	artificial	5-(CHNHC=OOCH2)	CH3	CH3	5-( 4-(S)-1,3-oxazolidin-2-one)-N,N-dimethyltryptamine	139264-17-8
	6-Fluoro-DMT	artificial	6-F	CH3	CH3	6-fluoro-N,N-dimethyltryptamine	1511-31-5
	6-Fluoro-DET [16]	artificial	6-F	CH2CH3	CH2CH3	6-fluoro-N,N-diethyltryptamine	2836-69-3
	6-Chloro-DMT	artificial	6-Cl	CH3	CH3	6-chloro-N,N-dimethyltryptamine	25390-72-1
	6-Methyl-DMT	artificial	6-CH3	CH3	CH3	6,N,N-trimethyltryptamine
	6-Hydroxy-DMT	artificial	6-OH	CH3	CH3	6-hydroxy-N,N-dimethyltryptamine	1476-33-1
	6-Hydroxy-DET	artificial	6-OH	CH3	CH3	6-hydroxy-N,N-diethyltryptamine	1476-59-1
	6-Methoxy-DMT	artificial	6-OCH3	CH3	CH3	6-methoxy-N,N-dimethyltryptamine	2426-88-2
	7-Methyl-DMT	artificial	7-CH3	CH3	CH3	7,N,N-trimethyltryptamine	65882-39-5
	7-Ethyl-DMT	artificial	7-CH2CH3	CH3	CH3	7-ethyl-N,N-dimethyltryptamine
	7-Chloro-DMT	artificial	7-Cl	CH3	CH3	7-chloro-N,N-dimethyltryptamine
	7-Bromo-DMT [17]	artificial	7-Br	CH3	CH3	7-bromo-N,N-dimethyltryptamine	74798-68-8
	7-Methoxy-DMT	artificial	7-OCH3	CH3	CH3	7-methoxy-N,N-dimethyltryptamine
	7-Methoxy-MiPT	artificial	7-OCH3	CH3	CH(CH3)2	7-methoxy-N-methyl-N-isopropyltryptamine
	1-Methylpsilocin	artificial	1-CH3, 4-OH	CH3	CH3	1-Methyl-3-[2-(N,N-dimethylamino)ethyl]-4-hydroxyindole	1465-16-3
	1-Methyl-5-MeO-DiPT	artificial	1-CH3, 5-OCH3	CH(CH3)2	CH(CH3)2	1-methyl-5-methoxy-N,N-diisopropyltryptamine	1373882-10-0
	NB-5-MeO-MiPT	artificial	1-OCOC(CH3)3, 5-OCH3	CH3	CH(CH3)2	1-(t-butoxycarbonyl)-5-methoxy-N-methyl-N-isopropyltryptamine
	NB-5-MeO-DALT	artificial	1-OCOC(CH3)3, 5-OCH3	H2C=CH-CH2	H2C=CH-CH2	1-(t-butoxycarbonyl)-5-methoxy-N,N-diallyltryptamine
	6-Fluoropsilocin	artificial	4-OH,6-F	CH3	CH3	4-hydroxy-6-fluoro-N,N-dimethyltryptamine	312314-12-8
	6-Fluoro-5-MeO-DMT	artificial	5-OCH3,6-F	CH3	CH3	5-methoxy-6-fluoro-N,N-dimethyltryptamine
	5,6-Difluoro-EPT	artificial	5-F, 6-F	CH2CH3	CH2CH2CH3	5,6-difluoro-N-ethyl-N-propyltryptamine
	5-MeO-2-TMT	artificial	2-CH3, 5-OCH3	CH3	CH3	2-(5-methoxy-2-methyl-H-indol-3-yl)-N,N-dimethylethanamine	67292-68-6
	5-Methoxy-7,N,N-trimethyltryptamine	artificial	5-OCH3, 7-CH3	CH3	CH3	5-Methoxy-7,N,N-trimethyltryptamine	61018-77-7
	5-Methoxy-4,N,N-trimethyltryptamine	artificial	4-CH3, 5-OCH3	CH3	CH3	5-Methoxy-4,N,N-trimethyltryptamine
	4-HO-5-MeO-DMT	artificial	4-OH, 5-OCH3	CH3	CH3	4-Hydroxy-5-methoxy-N,N-dimethyltryptamine	2433-31-0
	4-F-5-MeO-DMT	artificial	4-F, 5-OCH3	CH3	CH3	4-Fluoro-5-Methoxy-N,N-dimethyltryptamine	312314-18-4
	5-methoxy-7-fluoro-MET	artificial	5-OCH3, 7-F	CH3	CH2CH3	5-Methoxy-7-Fluoro-N-methyl-N-ethyltryptamine
	EMDT	artificial	2-CH2CH3, 5-OCH3	CH3	CH3	2-(2-ethyl-5-methoxy-1H-indol-3-yl)-N,N-dimethylethanamine	263744-72-5
	ST-1936	artificial	2-CH3, 5-Cl	CH3	CH3	2-(2-methyl-5-chloro-1H-indol-3-yl)-N,N-dimethylethanamine	1210-81-7
	O-4310	artificial	1-CH(CH3)2, 4-OH, 6-F	CH3	CH3	3-[2-(dimethylamino)ethyl]-6-fluoro-1-isopropyl-1H-indol-4-ol	885671-63-6
	CP-132,484	artificial	1-methyl-4,5-(OCH2CH2CH2)	H	H	1-(2-aminoethyl)-3-methyl-8,9-dihydropyrano(3,2-e)indole	143508-76-3
	4,5-DHP-DMT	artificial	4,5-(OCH2CH2CH2)	CH3	CH3	1-(2-dimethylaminoethyl)-8,9-dihydropyrano[3,2-e]indole	135360-97-3
	4,5-DHF-DMT (P-3)	artificial [18]	4,5-(CH2CH2O)	CH3	CH3	2-(3,6-dihydro-2H-furo[2,3-e]indol-8-yl)-N,N-dimethylethan-1-amine
	4,5-Methylbenzodioxole-DMT (P-131)	artificial	4,5-(OC(CH3)=N)	CH3	CH3	N,N-dimethyl-2-(2-methyl-6H-[1,3]oxazolo[4,5-e]indol-8-yl)ethan-1-amine
	4,5-MDO-DMT	artificial	4,5-(OCH2O)	CH3	CH3	2-(2H,6H-[1,3]Dioxolo[4,5-e]indol-8-yl)-N,N-dimethylethan-1-amine	81249-30-1
	4,5-MDO-DiPT	artificial	4,5-(OCH2O)	CH(CH3)2	CH(CH3)2	N-[2-(2H,6H-[1,3]Dioxolo[4,5-e]indol-8-yl)ethyl]-N-(propan-2-yl)propan-2-amine	82173-82-8
	5,6-FUR-DMT (P-4)	artificial	5,6-(CH=CHO)	CH3	CH3	2-(7H-furo[3,2-f]indol-5-yl)-N,N-dimethylethan-1-amine
	5,6-MDO-DMT	artificial	5,6-(OCH2O)	CH3	CH3	2-(2H,5H-[1,3]Dioxolo[4,5-f]indol-7-yl)-N,N-dimethylethan-1-amine
	5,6-MDO-MiPT	artificial	5,6-(OCH2O)	CH3	CH(CH3)2	N-[2-(2H,5H-[1,3]Dioxolo[4,5-f]indol-7-yl)ethyl]-N-methylpropan-2-amine
	5,6-MDO-DiPT	artificial	5,6-(OCH2O)	CH(CH3)2	CH(CH3)2	N-[2-(2H,5H-[1,3]Dioxolo[4,5-f]indol-7-yl)ethyl]-N-(propan-2-yl)propan-2-amine
Chemical Structure	Short Name	Origin	Ring Substitution	RN1	RN2	Full Name	CAS Number

List of substituted α-alkyltryptamines

α-Alkyltryptamines are a group of substituted tryptamines which possess an alkyl group, such as a methyl or ethyl group, attached at the alpha carbon, and in most cases no substitution on the amine nitrogen. ^{[19] [20] [21]} α-Alkylation of tryptamine makes it much more metabolically stable and resistant to degradation by monoamine oxidase, resulting in increased potency and greatly lengthened half-life. ^[21] This is analogous to α-methylation of phenethylamine into amphetamine. ^[21]

Many α-alkyltryptamines are drugs, acting as monoamine releasing agents, non-selective serotonin receptor agonists, and/or monoamine oxidase inhibitors, ^{[22] [23] [24] [25]} and produce psychostimulant, entactogen, and/or psychedelic effects. ^{[19] [20] [21]} The most well-known of these agents are α-methyltryptamine (αMT) and α-ethyltryptamine (αET), both of which were used clinically as antidepressants for a brief period of time in the past and are abused as recreational drugs. ^{[20] [21]} In accordance with its action as a dual releasing agent of serotonin and dopamine, αET has been found to produce serotonergic neurotoxicity similarly to amphetamines like MDMA and PCA, and the same is also likely to hold true for other serotonin and dopamine-releasing α-alkyltryptamines such as αMT, 5-MeO-αMT, and various others. ^[26]

Structure	Common name	Chemical name	CAS number
	Tryptophan	(2S)-2-amino-3-(1H-indol-3-yl)propanoic acid	73-22-3
	5-Hydroxytryptophan	2-amino-3-(5-hydroxy-1H-indol-3-yl)propanoic acid	4350-09-8
	αMT	1-(1H-Indol-3-yl)propan-2-amine	299-26-3
	4-HO-αMT	3-(2-aminopropyl)-1H-indol-4-ol	15066-09-8
	4-Methyl-αMT	1-methyl-2-(4-methyl-1H-indol-3-yl)-ethylamine	3569-29-7
	5-Fluoro-αMT	1-(5-fluoro-1H-indol-3-yl)propan-2-amine	712-08-3
	5-Chloro-αMT	1-(5-Chloro-1H-indol-3-yl)propan-2-amine	712-07-2
	5-HO-αMT (αMS/α-methyl-5-HT)	3-(2-aminopropyl)-1H-indol-5-ol	304-52-9
	5-MeO-αMT	1-(5-methoxy-1H-indol-3-yl)propan-2-amine	1137-04-8
	5-Ethoxy-αMT	1-(5-ethoxy-1H-indol-3-yl)propan-2-amine	101832-83-1
	5-Isopropoxy-αMT	1-{5-[(propan-2-yl)oxy]-1H-indol-3-yl}propan-2-amine
	BW-723C86	1-[5-(2-Thienylmethoxy)-1H-indol-3-yl]-2-propanamine	160521-72-2
	6-Fluoro-αMT	1-(6-fluoro-1H-indol-3-yl)propan-2-amine	712-11-8
	7-Chloro-AMT	1-(7-chloro-1H-indol-3-yl)propan-2-amine	711-99-9
	AL-37350A (4,5-dihydropyrano-αMT)	(S)-(+)-1-(2-Aminopropyl)-8,9-dihydropyrano[3,2-e]indole	362603-40-5
	Compound 5 [27]	1-(3H-benzo[e]indol-1-yl)propan-2-amine
	αET	1-(1H-indol-3-yl)butan-2-amine	2235-90-7
	4-Methyl-αET	1-(4-Methyl-1H-indol-3-yl)butan-2-amine	28289-30-7
	4-HO-αET	1-(4-hydroxy-1H-indol-3-yl)butan-2-amine	28289-28-3
	5-Fluoro-αET	1-(5-fluoro-1H-indol-3-yl)butan-2-amine	1380137-98-3
	5-Methyl-αET	1-(5-methyl-1H-indol-3-yl)butan-2-amine	1380148-21-9
	5-MeO-αET	1-(5-methoxy-1H-indol-3-yl)butan-2-amine	4765-10-0
	7-Methyl-αET	1-(7-methyl-1H-indol-3-yl)butan-2-amine	13712-80-6
	N-Methyl-5-MeO-αMT (α,N,O-TMS/α,N,O-trimethyl-5-HT)	[1-(5-methoxy-1H-indol-3-yl)propan-2-yl](methyl)amine	4822-13-3
	N,N-Dimethyl-αMT (α,N,N-TMT)	(2-(1H-Indol-3-yl)-1-methyl-ethyl)dimethylamine	4761-32-4
	N,N-Dimethyl-5-MeO-αMT (5-MeO-α,N,N-TMT)	(2-(5-methoxy-1H-Indol-3-yl)-1-methyl-ethyl)dimethylamine	101831-90-7
	αMDiPT	(2-(1H-Indol-3-yl)-1-methyl-ethyl)diisopropylamine
	MPMI [28]	3-[(1-methylpyrrolidin-2-yl)methyl]-1H-indole	143321-54-4
	Lucigenol	(R)-3-(N-methylpyrrolidin-2-ylmethyl)-4-hydoxyindole	250672-65-2
	5-MeO-MPMI	5-Methoxy-3-{[(2R)-1-methylpyrrolidin-2-yl]methyl}-1H-indole	143321-57-7
	5F-MPMI [29]	(R)-5-fluoro-3-[(1-methylpyrrolidin-2-yl)methyl]-1H-indole
	5-Br-MPMI	5-bromo-3-[(1-methylpyrrolidin-2-yl)methyl]-1H-indole	143322-57-0
	Eletriptan	3-{[(2R)-1-methylpyrrolidin-2-yl]methyl}-5-[2-(benzenesulfonyl)ethyl]-1H-indole	143322-58-1
	Z5247692566 [4] [30]	4-[(3,3-dimethyloxolan-2-yl)methyl]-3-[(1H-indol-3-yl)methyl]morpholine

Related compounds

A number of related compounds are known, with a similar structure but having the indole core flipped and/or replaced with related cores such as indoline, indazole, benzothiophene, or benzofuran. These similarly are primarily active as agonists at the 5-HT₂ family of serotonin receptors, with applications in the treatment of glaucoma, cluster headaches or as anorectics.

Structure	Common name	Chemical name	CAS number
	Dimemebfe	2-(5-Methoxy-1-benzofuran-3-yl)-N,N-dimethylethanamine	140853-58-3
	5-MeO-DiBF	N-[2-(5-Methoxy-1-benzofuran-3-yl)ethyl]-N-(propan-2-yl)propan-2-amine
	3-APB	3-(2-aminopropyl)benzofuran	105909-13-5
	Mebfap	3-(2-aminopropyl)-5-methoxybenzofuran	140853-59-4
	Ro60-0175	(S)-(6-chloro-5-fluoro-1H-indol-1-yl)propan-2-amine	169675-09-6
	AAZ-A-154	(2R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine
	Example 16 [31] [32]	1-(7-methoxyimidazo[1,5-a]pyridin-3-yl)-N,N-dimethylpropan-2-amine
	Example 1 [33]	1-(3-methyl-8,9-dihydropyrano[2,3-g]indol-1(7H)-yl)propan-2-amine
	VER-3323	(2S)-1-(6-bromo-2,3-dihydroindol-1-yl)propan-2-amine	259857-99-3
	AL-34662	1-((S)-2-Aminopropyl)-1H-indazol-6-ol	210580-75-9
	O-methyl-AL-34662	1-((S)-6-methoxy-2-aminopropyl)-1H-indazole	210580-60-2
	7-methyl-AL-34662	1-((S)-2-Aminopropyl)-7-methyl-1H-indazol-6-ol	874668-67-4
	7-chloro-AL-34662	1-((S)-2-Aminopropyl)-7-chloro-1H-indazol-6-ol	874881-86-4
	AL-38022A	(S)-2-(8,9-dihydro-7H-pyrano[2,3-g]indazol-1-yl)-1-methylethylamine	478132-11-5
	Example 9 [34]	(S)-α-methyl-pyrano[2,3-g]indazole-1(7H)-ethanamine	478132-12-6
	Example 3 [35]	(S)-7,8-dihydro-α-methyl-1H-[1,4]dioxino[2,3-g]indazole-1-ethanamine	890087-75-9
	Example 1 [36]	(S)-8,9-dihydro-α,9-dimethylpyrazolo[3,4-f][1,4]benzoxazine-1(7H)-ethanamine	1373917-69-1
	YM-348	(2S)-1-(7-ethyl-1H-furo[2,3-g]indazol-1-yl)propan-2-amine	372163-84-3
	2-desethyl-YM-348 [37]	(2S)-1-(1H-furo[2,3-g]indazol-1-yl)propan-2-amine	748116-94-1
	I-32 [38]	3-(1-methylpyrrolidin-3-yl)-1H-indol-4-ol
	2-Azapsilocin (Psilocin indazole analogue, P-6) [39]	3-[2-(dimethylamino)ethyl]-1H-indazol-4-ol
	4-Aza-5-MeO-DPT (P-11)	N-[2-(5-methoxy-1H-pyrrolo[3,2-b]pyridin-3-yl)ethyl]-N-propylpropan-1-amine
	5-Aza-4-MeO-DiPT (P-36)	N-[2-(4-methoxy-1H-pyrrolo[3,2-c]pyridin-3-yl)ethyl]-N-(propan-2-yl)propan-2-amine
	7-Aza-5-MeO-DiPT (P-19)	N-[2-(5-methoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)ethyl]-N-(propan-2-yl)propan-2-amine
	VU6067416 [40]	3-(1,2,5,6-tetrahydropyridin-3-yl)-5-bromo-1H-indazole
	(R)-69	3-[(5R)-5-methyl-1,2,5,6-tetrahydropyridin-3-yl]-1H-pyrrolo[2,3-b]pyridine
	SN-22	3-(1-methylpiperidin-4-yl)-1H-indole	17403-07-5

Further reading

• TiHKAL

See also

• Ergoline
• Lysergamide
• Iboga alkaloid
• Substituted amphetamine
• Substituted benzofuran
• Substituted cathinone
• Substituted methylenedioxyphenethylamine
• Substituted phenethylamine
• 2C, DOx, 25-NB
• List of miscellaneous 5HT2A agonists

References

1. Chemistry, University of; Prague, Technology. "Concentrations of psychoactive compounds in mushrooms found to be extremely variable". phys.org. Retrieved 2022-12-26.
2. Toro-Sazo M, Brea J, Loza MI, Cimadevila M, Cassels BK (2019). "5-HT2 receptor binding, functional activity and selectivity in N-benzyltryptamines". PLOS ONE. 14 (1): e0209804. Bibcode:2019PLoSO..1409804T. doi: 10.1371/journal.pone.0209804 . PMC   6328172 . PMID   30629611.
3. Jensen N. Tryptamines as Ligands and Modulators of the Serotonin 5-HT2A Receptor and the Isolation of Aeruginascin from the Hallucinogenic Mushroom Inocybe aeruginascens. PhD thesis, University of Göttingen, 2004
4. Lyu J, Kapolka N, Gumpper R, Alon A, Wang L, Jain MK, et al. (December 2023). "AlphaFold2 structures template ligand discovery". bioRxiv. doi:10.1101/2023.12.20.572662. PMC   10769324 . PMID   38187536.
5. McKay JB, Parkhurst RM, Silverstein RM, Skinner WA (October 1963). "Analogues of Psilocin and Lysergic acid diethylamide I. Chloro, Nitro, and Amino Derivatives of 3-Substituted Indoles". Canadian Journal of Chemistry. 41 (10): 2585–2590. doi:10.1139/v63-378.
6. Klein AK, Chatha M, Laskowski LJ, Anderson EI, Brandt SD, Chapman SJ, McCorvy JD, Halberstadt AL (April 2021). "Investigation of the Structure-Activity Relationships of Psilocybin Analogues". ACS Pharmacology & Translational Science. 4 (2): 533–542. doi:10.1021/acsptsci.0c00176. PMC   8033608 . PMID   33860183.
7. Pham DN, Chadeayne AR, Golen JA, Manke DR (February 2021). "Psilacetin derivatives: fumarate salts of the meth-yl-ethyl, meth-yl-allyl and diallyl variants of the psilocin prodrug". Acta Crystallographica Section E. 77 (Pt 2): 101–106. Bibcode:2021AcCrE..77..101P. doi:10.1107/S2056989021000116. PMC   7869532 . PMID   33614134.
8. Sherwood AM, Burkhartzmeyer EK, Williamson SE, Baumann MH, Glatfelter GC. Psychedelic-like Activity of Norpsilocin Analogues. ACS Chem Neurosci. 2024 Jan 17;15(2):315-327. doi : 10.1021/acschemneuro.3c00610 PMID   38189238
9. WO 2023115167,Banister S, Jorgensen W, Jinlong T,"Compounds",published 29 June 2023, assigned to Psylo Pty Ltd. 
10. WO 2021179091,Kozikowski A, Shaprio G, Tueckmantel W, McCorvy J,"3-(2-(Aminoethyl)-indol-4-ol derivatives, methods of preparation thereof, and the use as 5-HT2 receptor modulators",published 16 September 2021, assigned to Bright Minds Biosciences Inc.and The Medical College Of Wisconsin Inc. 
11. WO 2021101926,Stamets PE,"Tryptamine Compositions for Enhancing Neurite Outgrowth.",published 2021-05-27, assigned to Stamets Paul Edward. 
12. WO 2021168082,Kruegel AC, Sporn J,"Specific Tryptamines for use in the Treatment of Mood Disorders.",published 26 August 2021 
13. Xu YC, Schaus JM, Walker C, Krushinski J, Adham N, Zgombick JM, Liang SX, Kohlman DT, Audia JE (February 1999). "N-Methyl-5-tert-butyltryptamine: A novel, highly potent 5-HT1D receptor agonist". Journal of Medicinal Chemistry. 42 (3): 526–31. doi:10.1021/jm9805945. PMID   9986723.
14. WO 2022235927,Kruegel AC,"Novel Tryptamines and Methods of Treating Mood Disorders",published 10 November 2022, assigned to Gilgamesh Pharmaceuticals, Inc. 
15. Shaw E, Woolley DW (April 1953). "The synthesis of nitro-and aminoindoles analogous to serotonin". Journal of the American Chemical Society. 75 (8): 1877–1881. doi:10.1021/ja01104a029.
16. Rabin RA, Regina M, Doat M, Winter JC (May 2002). "5-HT2A receptor-stimulated phosphoinositide hydrolysis in the stimulus effects of hallucinogens". Pharmacology, Biochemistry, and Behavior. 72 (1–2): 29–37. doi:10.1016/s0091-3057(01)00720-1. PMID   11900766. S2CID   6480715.
17. Glennon RA, Schubert E, Jacyno JM, Rosecrans JA (November 1980). "Studies on several 7-substituted N,N-dimethyltryptamines". Journal of Medicinal Chemistry. 23 (11): 1222–6. doi:10.1021/jm00185a014. PMID   6779006.
18. WO 2023115166,Banister S, Jorgensen W, Jinlong T,"Compounds",published 29 June 2023, assigned to Psylo Pty Ltd. 
19. Ries RK, Miller SC, Fiellin DA (2009). Principles of Addiction Medicine. Lippincott Williams & Wilkins. pp. 216–218. ISBN   978-0-7817-7477-2.
20. Laing RR (2003). Hallucinogens: A Forensic Drug Handbook. Academic Press. pp. 102–. ISBN   978-0-12-433951-4.
21. Lemke TL, Williams DA (24 January 2012). Foye's Principles of Medicinal Chemistry. Lippincott Williams & Wilkins. pp. 641–. ISBN   978-1-60913-345-0.
22. Nagai F, Nonaka R, Satoh Hisashi Kamimura K (March 2007). "The effects of non-medically used psychoactive drugs on monoamine neurotransmission in rat brain". European Journal of Pharmacology. 559 (2–3): 132–7. doi:10.1016/j.ejphar.2006.11.075. PMID   17223101.
23. Blough BE, Landavazo A, Partilla JS, Decker AM, Page KM, Baumann MH, Rothman RB (October 2014). "Alpha-ethyltryptamines as dual dopamine-serotonin releasers". Bioorganic & Medicinal Chemistry Letters. 24 (19): 4754–4758. doi:10.1016/j.bmcl.2014.07.062. PMC   4211607 . PMID   25193229.
24. Nonaka R, Nagai F, Ogata A, Satoh K (December 2007). "In vitro screening of psychoactive drugs by [(35)S]GTPgammaS binding in rat brain membranes". Biological & Pharmaceutical Bulletin. 30 (12): 2328–33. doi: 10.1248/bpb.30.2328 . PMID   18057721.
25. Feldman JM, Chapman B (December 1975). "Monoamine oxidase inhibitors: nature of their interaction with rabbit pancreatic islets to alter insluin secretion". Diabetologia. 11 (6): 487–94. doi: 10.1007/bf01222097 . PMID   1107123.
26. Huang XM, Johnson MP, Nichols DE (July 1991). "Reduction in brain serotonin markers by alpha-ethyltryptamine (Monase)". European Journal of Pharmacology. 200 (1): 187–90. doi:10.1016/0014-2999(91)90686-K. PMID   1722753.
27. Chang-Fong J, Addo J, Dukat M, Smith C, Mitchell NA, Herrick-Davis K, Teitler M, Glennon RA (January 2002). "Evaluation of isotryptamine derivatives at 5-HT(2) serotonin receptors". Bioorganic & Medicinal Chemistry Letters. 12 (2): 155–8. doi:10.1016/s0960-894x(01)00713-2. PMID   11755343.
28. US 5607951,Macor JE, Wythes MJ,"Indole derivatives",issued 4 March 1997, assigned to Pfizer, Inc. 
29. WO 2022256554,Wallach J, Dybek M,"Fluorinated Tryptamine Compounds, Analogues Thereof, and Methods Using Same.",published 8 December 2022, assigned to University Of The Sciences. 
30. Callaway E (18 January 2024). "AlphaFold found thousands of possible psychedelics. Will its predictions help drug discovery?". Nature News. 626 (7997): 14–15. Bibcode:2024Natur.626...14C. doi:10.1038/d41586-024-00130-8. PMID   38238624. S2CID   267040499.
31. Kargbo RB. Neuropharmacological Advances: Harnessing 5-HT2A Receptor Modulators and Psychoplastogens. ACS Med Chem Lett. 2024 Jan 23;15(2):171-173. doi : 10.1021/acsmedchemlett.4c00003 PMID   38352827
32. Powell NA, Chytil M. Imidazopyridine psychoplastogens and uses thereof. WO 2023/114844
33. USgranted 7012090,Chen HH, May JA,"Pyranoindoles for treating glaucoma",published 17 March 2000,issued 14 March 2006, assigned to Alcon, Inc. 
34. USgranted 6881749,Chen HH, May JA, Severns BS,"Pyranoindazoles and their use for the treatment of glaucoma",published 3 June 2004,issued 19 April 2005, assigned to Alcon, Inc. 
35. USgranted 7425572,Chen HH, May JA,"Use of dioxindoindazoles and dioxoloindazoles for treating glaucoma",published 8 June 2006,issued 16 September 2008, assigned to Alcon, Inc. 
36. USgranted 7268131,Dantanarayana AP, May JA,"Substituted [1,4]oxazino[2,3-g]indazoles for the treatment of glaucoma",published 15 December 2005,issued 11 September 2007, assigned to Alcon, Inc. 
37. Shimada I, Maeno K, Kazuta K, Kubota H, Kimizuka T, Kimura Y, et al. (February 2008). "Synthesis and structure-activity relationships of a series of substituted 2-(1H-furo[2,3-g]indazol-1-yl)ethylamine derivatives as 5-HT2C receptor agonists". Bioorganic & Medicinal Chemistry. 16 (4): 1966–82. doi:10.1016/j.bmc.2007.10.100. PMID   18035544.
38. WO 2022120475,Slassi A, Araujo J, Higgins G,"3-Cyclic Amine-Indole Derivatives as Serotonergic Agents for the Treatment of CNS Disorders.",published 16 June 2022, assigned to Mindset Pharma Inc. 
39. WO 2023115165,Banister S, Jorgensen W, Jinlong T,"Compounds",published 29 June 2023, assigned to Psylo Pty Ltd. 
40. Jayakodiarachchi N, et al. Evaluation of the Indazole Analogs of 5-MeO-DMT and Related Tryptamines as Serotonin Receptor 2 Agonists. ACS Med. Chem. Lett. 2024 doi : 10.1021/acsmedchemlett.3c00566