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.
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 |
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 | ||
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 |
α-Methyltryptamine is a psychedelic, stimulant, and entactogen drug of the tryptamine class. It was originally developed as an antidepressant by chemists at Upjohn in the 1960s, and was used briefly as an antidepressant in Russia under the trade name Indopan before being discontinued.
α-Ethyltryptamine, also known as etryptamine, is a psychedelic, stimulant, and entactogenic drug of the tryptamine class. It was originally developed and marketed as an antidepressant under the brand name Monase by Upjohn in the 1960s.
Psilocin is a substituted tryptamine alkaloid and a serotonergic psychedelic substance. It is present in most psychedelic mushrooms together with its phosphorylated counterpart psilocybin. Psilocin is a Schedule I drug under the Convention on Psychotropic Substances. Acting on the 5-HT2A serotonin receptors, psilocin’s psychedelic effects are directly correlated with the drug's occupancy at these receptor sites. The subjective mind-altering effects of psilocin are highly variable and are said to resemble those of LSD and DMT.
Indole alkaloids are a class of alkaloids containing a structural moiety of indole; many indole alkaloids also include isoprene groups and are thus called terpene indole or secologanin tryptamine alkaloids. Containing more than 4100 known different compounds, it is one of the largest classes of alkaloids. Many of them possess significant physiological activity and some of them are used in medicine. The amino acid tryptophan is the biochemical precursor of indole alkaloids.
(+)-CPCA is a stimulant drug similar in structure to pethidine and to RTI-31, but nocaine lacks the two-carbon bridge of RTI-31's tropane skeleton. This compound was first developed as a substitute agent for cocaine.
AL-34662 is an indazole derivative drug that is being developed for the treatment of glaucoma. It acts as a selective 5-HT2A receptor agonist, the same target as that of psychedelic drugs like psilocin, but unlike these drugs, AL-34662 was designed specifically as a peripherally selective drug, which does not cross the blood–brain barrier. This means that AL-34662 can exploit a useful side effect of the hallucinogenic 5-HT2A agonists, namely reduction in intra-ocular pressure and hence relief from the symptoms of glaucoma, but without causing the hallucinogenic effects that make centrally active 5-HT2A agonists unsuitable for clinical use. In animal studies, AL-34662 has been shown to be potent and effective in the treatment of symptoms of glaucoma, with minimal side effects.
AL-37350A (4,5-DHP-AMT) is a tricyclic tryptamine derivative which acts as a potent and selective agonist for the serotonin receptor 5-HT2A, with a Ki of 2.0 nM, and moderate selectivity over the related 5-HT2B and 5-HT2C receptors. It has been shown to have ocular hypotensive activity in animal models, suggesting it may be useful for the treatment of glaucoma.
5-Methoxy-7,N,N-trimethyltryptamine (5-MeO-7,N,N-TMT, 5-MeO-7-TMT), is a tryptamine derivative which acts as a partial agonist at the 5-HT2 serotonin receptors, with an EC50 of 63.9 nM and an efficacy of 66.2% at 5-HT2A (vs 5-HT), and weaker activity at 5-HT2B and 5-HT2C. In animal tests, both 7,N,N-TMT and 5-MeO-7,N,N-TMT produced behavioural responses similar to those of psychedelic drugs such as DMT and 5-MeO-DMT, but compounds with larger 7-position substituents such as 7-ethyl-DMT and 7-bromo-DMT did not produce psychedelic-appropriate responding despite high 5-HT2 receptor binding affinity, suggesting these may be antagonists or weak partial agonists for the 5-HT2 receptors. The related compound 7-MeO-MiPT (cf. 5-MeO-MiPT) was also found to be inactive, suggesting that the 7-position has poor tolerance for bulky groups at this position, at least if agonist activity is desired.
7,N,N-trimethyltryptamine (7-methyl-DMT, 7-TMT), is a tryptamine derivative which acts as an agonist of 5-HT2 receptors. In animal tests, both 7-TMT and its 5-methoxy derivative 5-MeO-7-TMT produced behavioural responses similar to those of psychedelic drugs such as DMT, but the larger 7-ethyl and 7-bromo derivatives of DMT did not produce psychedelic responses despite having higher 5-HT2 receptor affinity in vitro (cf. DOBU, DOAM). 7-TMT also weakly inhibits reuptake of serotonin but with little effect on dopamine or noradrenaline reuptake.
7-Methyl-α-ethyltryptamine (7-Me-αET) is a tryptamine derivative related to α-ethyltryptamine (αET). It was discovered by a team at Upjohn in the early 1960s. It has similar pharmacological effects to αET, but is both 3-4 times more potent as a serotonin releasing agent, and 10 times more potent as a monoamine oxidase inhibitor, making it potentially hazardous as this pharmacological profile is shared with drugs such as PMA and 4-MTA, which are known to be dangerous in humans when used at high doses.
1-(2-Dimethylaminoethyl)dihydropyrano(3,2-e)indole (4,5-DHP-DMT) is a tricyclic tryptamine derivative which acts as a potent and reasonably selective partial agonist for the serotonin receptor 5-HT2A, with a Ki of 17.0 nM, and moderate selectivity over related serotonin receptors. It has lower 5-HT2 affinity and efficacy than the related compound AL-37350A, but higher lipophilicity.
MN-25 (UR-12) is a drug invented by Bristol-Myers Squibb, that acts as a reasonably selective agonist of peripheral cannabinoid receptors. It has moderate affinity for CB2 receptors with a Ki of 11 nM, but 22x lower affinity for the psychoactive CB1 receptors with a Ki of 245 nM. The indole 2-methyl derivative has the ratio of affinities reversed however, with a Ki of 8 nM at CB1 and 29 nM at CB2, which contrasts with the usual trend of 2-methyl derivatives having increased selectivity for CB2 (cf. JWH-018 vs JWH-007, JWH-081 vs JWH-098).
CP-132,484 is a tryptamine derivative which acts as a potent and selective agonist for the 5-HT2 family of serotonin receptors. It has reasonable selectivity for 5-HT2A and 5-HT2C subtypes over 5-HT2B, but is only slightly selective for 5-HT2A over 5-HT2C. This compound and several related analogues have been shown to have ocular hypotensive activity in animal models, suggesting they may be useful for the treatment of glaucoma.
5-Chloro-α-methyltryptamine (5-Chloro-αMT), also known as PAL-542, is a tryptamine derivative related to α-methyltryptamine (αMT) and one of only a few known specific serotonin-dopamine releasing agents (SDRAs). It has been investigated in animals as a potential treatment for cocaine dependence. The EC50 values of 5-chloro-αMT in evoking the in vitro release of serotonin (5-HT), dopamine (DA), and norepinephrine (NE) in rat synaptosomes were reported as 16 nM, 54 nM, and 3434 nM, with an NE/DA ratio of 63.6 and a DA/5-HT ratio of 3.38, indicating that it is a highly specific and well-balanced SDRA. However, 5-chloro-αMT has also been found to act as a potent full agonist of the 5-HT2A receptor, with an EC50 value of 6.27 nM and an efficacy of 105%. It is likely to act as a potent agonist of other serotonin receptors as well.
Substituted phenylmorpholines, or substituted phenmetrazines alternatively, are chemical derivatives of phenylmorpholine or of the psychostimulant drug phenmetrazine. Most such compounds act as releasers of monoamine neurotransmitters, and have stimulant effects. Some also act as agonists at serotonin receptors, and compounds with an N-propyl substitution act as dopamine receptor agonists. A number of derivatives from this class have been investigated for medical applications, such as for use as anorectics or medications for the treatment of ADHD. Some compounds have also become subject to illicit use as designer drugs.
7-Chloro-α-methyltryptamine (7-Cl-AMT) is a tryptamine derivative with stimulant effects, invented in the 1960s. It is a weak monoamine oxidase inhibitor but its pharmacology has not otherwise been studied by modern techniques, though several closely related compounds are known to act as serotonin–dopamine releasing agents and agonists of the 5-HT2A receptor.
5-Fluoro-α-ethyltryptamine (5-F-AET) is a tryptamine derivative which acts as a serotonin–dopamine releasing agent and agonist of the 5-HT2A receptor.
5-Fluoro-DET is a tryptamine derivative related to drugs such as DET and 5-MeO-DET. It acts as an inhibitor of the enzyme myeloperoxidase, and is also thought to be an agonist at the 5-HT2A receptor.
RS134-49 is a tetrahydropyridine derivative related to psychedelic tryptamines which acts as a 5-HT2A receptor agonist, with a 5-HT2A Ki of 11.5nM and an EC50 of 22nM. It is a biased agonist selective for activation of the Gq coupled signalling pathway with weaker activation of the β-arrestin 2 coupled pathway, but shows a more balanced profile than related compounds such as (R)-69.