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.
![](http://upload.wikimedia.org/wikipedia/commons/thumb/e/e4/Tryptamine_rests_General_Formula_V.svg/220px-Tryptamine_rests_General_Formula_V.svg.png)
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
editChemical 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
editα-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
editA 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
editSee also
editReferences
edit- ^ Chemistry, University of; Prague, Technology. "Concentrations of psychoactive compounds in mushrooms found to be extremely variable". phys.org. Retrieved 2022-12-26.
- ^ 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.
- ^ 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
- ^ a b 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.
- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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
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- ^ 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.
- ^ WO 2022235927, Kruegel AC, "Novel Tryptamines and Methods of Treating Mood Disorders", published 10 November 2022, assigned to Gilgamesh Pharmaceuticals, Inc.
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