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 |
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Tryptamine | Animals, plants, fungi | H | H | H | 3-(2-aminoethyl)indole / 2-(1H-indol-3-yl)ethanamine | 61-54-1 |
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NMT | Plants | H | H | CH3 | N-methyltryptamine | 61-49-4 |
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2-HO-NMT | Plants | 2-OH | H | CH3 | 2-hydroxy-N-methyltryptamine | 106987-89-7 |
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5-MeO-NMT | Plants | 5-OCH3 | H | CH3 | 5-methoxy-N-methyltryptamine | 2009-03-2 |
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Serotonin | Animals, plants | 5-OH | H | H | 5-hydroxytryptamine | 50-67-9 |
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Nω-Methylserotonin (norbufotenin) | Plants | 5-OH | H | CH3 | 5-hydroxy-N-methyltryptamine | 1134-01-6 |
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Bufotenin | Animals, plants, fungi | 5-OH | CH3 | CH3 | 5-hydroxy-N,N-dimethyltryptamine | 487-93-4 |
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Bufotenidine | Amphibians | 5-O− | (CH3)3 | 3-[2-(trimethylazaniumyl)ethyl]-1H-indol-5-olate | 487-91-2 | |
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Melatonin | Animals, plants, microbes | 5-OCH3 | H | O=C-CH3 | 5-methoxy-N-acetyltryptamine | 73-31-4 |
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N-Acetylserotonin | Animals | 5-OH | H | O=C-CH3 | 5-hydroxy-N-acetyltryptamine | 1210-83-9 |
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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 |
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4-HO-NMT | Fungi | 4-OH | H | CH3 | 4-hydroxy-N-methyltryptamine | 28363-70-4 |
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Psilocin | Fungi | 4-OH | CH3 | CH3 | 4-hydroxy-N,N-dimethyltryptamine | 520-53-6 |
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Norbaeocystin | Fungi | 4-OPO3H2 | H | H | 4-phosphoryloxy-tryptamine | 21420-59-7 |
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Baeocystin | Fungi | 4-OPO3H2 | H | CH3 | 4-phosphoryloxy-N-methyl-tryptamine | 21420-58-6 |
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Psilocybin | Fungi | 4-OPO3H2 | CH3 | CH3 | 4-phosphoryloxy-N,N-dimethyltryptamine | 520-52-5 |
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Aeruginascin | Fungi | 4-OPO3H2 | (CH3)3 | [3-[2-(trimethylazaniumyl)ethyl]-1H-indol-4-yl] hydrogen phosphate | 114264-95-8 | |
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DMT | Animals, plants | H | CH3 | CH3 | N,N-dimethyltryptamine | 61-50-7 |
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Lespedamine | Plants | 1-OCH3 | CH3 | CH3 | 1-methoxy-N,N-dimethyltryptamine | 4335-93-7 |
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5-MeO-DMT | Animals, plants | 5-OCH3 | CH3 | CH3 | 5-methoxy-N,N-dimethyltryptamine | 1019-45-0 |
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5-Bromo-DMT | Marine sponges, invertebrates | 5-Br | CH3 | CH3 | 5-bromo-N,N-dimethyltryptamine | 17274-65-6 |
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6-Bromotryptamine | Marine invertebrates | 6-Br | H | H | 6-bromotryptamine | 96624-18-9 |
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5,6-Dibromotryptamine | Marine invertebrates | 5,6-Br | H | H | 5,6-dibromotryptamine | |
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5,6-Dibromo-NMT | Marine invertebrates | 5,6-Br | H | CH3 | 5,6-dibromo-N-methyltryptamine | |
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5,6-Dibromo-DMT | Marine sponges, invertebrates | 5,6-Br | CH3 | CH3 | 5,6-dibromo-N,N-dimethyltryptamine | 72853-80-6 |
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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 |
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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 |
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Acetryptine | artificial | 5-COCH3 | H | H | 5-Acetyltryptamine | 3551-18-6 |
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5-BT | artificial | 5-OCH2C6H5 | H | H | 5-Benzyloxytryptamine | 20776-45-8 |
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5-CT | artificial | 5-CONH2 | H | H | 5-Carboxamidotryptamine | 74885-09-9 |
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5-(Nonyloxy)tryptamine | artificial | 5-O(CH2)8CH3 | H | H | 5-nonyloxytryptamine | 157798-12-4 |
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2-Methyl-5-hydroxytryptamine | artificial | 2-CH3, 5-OH | H | H | 3-(2-aminoethyl)-2-methyl-1H-indol-5-ol | 78263-90-8 |
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NET | artificial | H | H | CH2CH3 | N-ethyltryptamine | 61-53-0 |
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NiPT | artificial | H | H | CH(CH3)2 | N-isopropyltryptamine | 14121-10-9 |
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NcPT | artificial | H | H | C3H5 | N-cyclopropyltryptamine | |
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NSBT | artificial | H | H | CH(CH3)CH2CH3 | N-sec-butyltryptamine | |
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NTBT | artificial | H | H | C(CH3)3 | N-[2-(1H-indol-3-yl)ethyl]-2-methylpropan-2-amine | |
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5-MT-NBOMe | artificial | 5-OCH3 | H | CH2C6H4(o-OCH3) | 5-methoxy-N-(ortho-methoxybenzyl)tryptamine | 1335331-37-7 |
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5-MT-NB3OMe [2] | artificial | 5-OCH3 | H | CH2C6H4(m-OCH3) | 5-methoxy-N-(meta-methoxybenzyl)tryptamine | 1648553-42-7 |
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5-MeO-NBpBrT | artificial | 5-OCH3 | H | CH2C6H4(p-Br) | N-(4-Bromobenzyl)-2-(5-methoxy-1H-indol-3-yl)ethanamine | 155639-13-7 |
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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 | |
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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 |
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Pyr-T | artificial | H | (CH2)4 | 3-[2-(Pyrrolidin-1-yl)ethyl]-1H-indole | 14008-96-9 | |
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4-HO-pyr-T | artificial | 4-OH | (CH2)4 | 3-[2-(Pyrrolidin-1-yl)ethyl]-1H-indol-4-ol | 63097-26-7 | |
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5-MeO-pyr-T | artificial | 5-OCH3 | (CH2)4 | 5-Methoxy-3-[2-(pyrrolidin-1-yl)ethyl]-1H-indole | 3949-14-2 | |
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MET | artificial | H | CH3 | CH2CH3 | N-Methyl-N-ethyltryptamine | 5599-69-9 |
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MPT | artificial | H | CH3 | CH2CH2CH3 | N-Methyl-N-propyltryptamine | 850032-72-3 |
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MiPT | artificial | H | CH3 | CH(CH3)2 | N-Methyl-N-isopropyltryptamine | 96096-52-5 |
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McPT | artificial | H | CH3 | C3H5 | N-Methyl-N-cyclopropyltryptamine | 1373918-63-8 |
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EcPT | artificial | H | CH2CH3 | C3H5 | N-ethyl-N-cyclopropyltryptamine | |
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PcPT | artificial | H | CH2CH2CH3 | C3H5 | N-propyl-N-cyclopropyltryptamine | |
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iPcPT | artificial | H | CH(CH3)2 | C3H5 | N-isopropyl-N-cyclopropyltryptamine | |
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DcPT | artificial | H | C3H5 | C3H5 | N,N-dicyclopropyltryptamine | 1373918-62-7 |
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MBT | artificial | H | CH3 | (CH2)3CH3 | N-Methyl-N-butyltryptamine | 848130-12-1 |
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MSBT | artificial | H | CH3 | CH(CH3)CH2CH3 | N-Methyl-N-sec-butyltryptamine | |
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MiBT | artificial | H | CH3 | CH2CH(CH3)2 | N-Methyl-N-iso-butyltryptamine | |
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McPMT | artificial | H | CH3 | CH2C3H5 | N-Methyl-N-(cyclopropylmethyl)tryptamine | |
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DET | artificial | H | CH2CH3 | CH2CH3 | N,N-diethyltryptamine | 61-51-8 |
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EPT | artificial | H | CH2CH3 | CH2CH2CH3 | N-Ethyl-N-propyltryptamine | 850032-68-7 |
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EiPT | artificial | H | CH2CH3 | CH(CH3)2 | N-Ethyl-N-isopropyltryptamine | 848130-11-0 |
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DPT | artificial | H | CH2CH2CH3 | CH2CH2CH3 | N,N-dipropyltryptamine | 61-52-9 |
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PiPT | artificial | H | CH2CH2CH3 | CH(CH3)2 | N-Propyl-N-isopropyltryptamine | 1354632-00-0 |
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DiPT | artificial | H | CH(CH3)2 | CH(CH3)2 | N,N-diisopropyltryptamine | 14780-24-6 |
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EBT | artificial | H | CH2CH3 | (CH2)3CH3 | N-ethyl-N-butyltryptamine | |
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PBT | artificial | H | CH2CH2CH3 | (CH2)3CH3 | N-propyl-N-butyltryptamine | |
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iPsBT | artificial | H | CH(CH3)2 | CH(CH3)CH2CH3 | N-isopropyl-N-sec-butyltryptamine | |
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DBT | artificial | H | (CH2)3CH3 | (CH2)3CH3 | N,N-dibutyltryptamine | 15741-77-2 |
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DIBT | artificial | H | CH2CH(CH3)2 | CH2CH(CH3)2 | N,N-diisobutyltryptamine | 63938-64-7 |
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DSBT | artificial | H | CH(CH3)CH2CH3 | CH(CH3)CH2CH3 | N,N-disecbutyltryptamine | |
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MALT | artificial | H | CH3 | H2C=CH-CH2 | N-methyl-N-allyltryptamine | 1366416-29-6 |
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DALT | artificial | H | H2C=CH-CH2 | H2C=CH-CH2 | N,N-diallyltryptamine | 60676-77-9 |
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ALiPT | artificial | H | H2C=CH-CH2 | CH(CH3)2 | N-allyl-N-isopropyltryptamine | |
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2-Methyl-DMT | artificial | 2-CH3 | CH3 | CH3 | (2-(2-methyl-1H-indol-3-yl)-1-methyl-ethyl)dimethylamine | 1080-95-1 |
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2-Me-DET | artificial | 2-CH3 | CH2CH3 | CH2CH3 | N,N-Diethyl-2-(2-methyl-1H-indol-3-yl)ethan-1-amine | 26628-88-6 |
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4-Amino-DMT [4] | artificial | 4-NH2 | CH3 | CH3 | 4-amino-N,N-dimethyltryptamine | 60331-61-5 |
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4-Methyl-DMT | artificial | 4-CH3 | CH3 | CH3 | 4,N,N-trimethyltryptamine | 28289-23-8 |
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4-MeO-DMT | artificial | 4-OCH3 | CH3 | CH3 | 4-methoxy-N,N-dimethyltryptamine | 3965-97-7 |
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4-MeO-MiPT | artificial | 4-OCH3 | CH3 | CH(CH3)2 | 4-methoxy-N-methyl-N-isopropyltryptamine | 96096-53-6 |
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4-MeO-DiPT | artificial | 4-OCH3 | CH(CH3)2 | CH(CH3)2 | 4-methoxy-N,N-diisopropyltryptamine | |
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4-AcO-DMT | artificial | 4-OCOCH3 | CH3 | CH3 | 4-acetoxy-N,N-dimethyltryptamine | 92292-84-7 |
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4-PrO-DMT | artificial | 4-OCOCH2CH3 | CH3 | CH3 | 4-propionyloxy-N,N-dimethyltryptamine | 1373882-11-1 |
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4-HO-MET | artificial | 4-OH | CH3 | CH2CH3 | 4-hydroxy-N-methyl-N-ethyltryptamine | 77872-41-4 |
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4-Acetoxy-MET | artificial | 4-OCOCH3 | CH3 | CH2CH3 | 4-acetoxy-N-methyl-N-ethyltryptamine | 1445751-40-5 |
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4-PO-MET | artificial | 4-OPO3H2 | CH3 | CH2CH3 | 4-phosphoryloxy-N-methyl-N-ethyltryptamine | |
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4-HO-DET | artificial | 4-OH | CH2CH3 | CH2CH3 | 4-hydroxy-N,N-diethyltryptamine | 22204-89-3 |
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4-Acetoxy-DET | artificial | 4-OCOCH3 | CH2CH3 | CH2CH3 | 4-acetoxy-N,N-diethyltryptamine | 1135424-15-5 |
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4-PO-DET | artificial | 4-OPO3H2 | CH2CH3 | CH2CH3 | 4-phosphoryloxy-N,N-diethyltryptamine | 60480-02-6 |
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4-HO-EPT | artificial | 4-OH | CH2CH3 | CH2CH2CH3 | 4-hydroxy-N-ethyl-N-propyltryptamine | 2595431-59-5 |
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4-PO-EPT | artificial | 4-OPO3H2 | CH2CH3 | CH2CH2CH3 | 4-phosphoryloxy-N-ethyl-N-propyltryptamine | |
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4-AcO-EiPT | artificial | 4-OCOCH3 | CH2CH3 | CH(CH3)2 | 4-acetoxy-N-ethyl-N-isopropyltryptamine | |
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4-HO-MPT | artificial | 4-OH | CH3 | CH2CH2CH3 | 4-hydroxy-N-methyl-N-propyltryptamine | 763035-03-6 |
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4-HO-MiPT | artificial | 4-OH | CH(CH3)2 | CH3 | 4-hydroxy-N-isopropyl-N-methyltryptamine | 77872-43-6 |
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4-Acetoxy-MiPT | artificial | 4-OCOCH3 | CH3 | CH(CH3)2 | 4-acetoxy-N-methyl-N-isopropyltryptamine | 1024612-25-6 |
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4-HO-MALT[5] | artificial | 4-OH | CH3 | H2C=CH-CH2 | 4-hydroxy-N-Methyl-N-allyltryptamine | |
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4-AcO-MALT [6] | artificial | 4-OCOCH3 | CH3 | H2C=CH-CH2 | 4-acetoxy-N-Methyl-N-allyltryptamine | |
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4-HO-MSBT | artificial | 4-OH | CH(CH3)CH2CH3 | CH3 | 4-hydroxy-N-sec-butyl-N-methyltryptamine | |
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4-HO-EiBT | artificial[7] | 4-OH | CH2CH(CH3)2 | CH2CH3 | 4-hydroxy-N-iso-butyl-N-ethyltryptamine | |
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4-HO-McPT | artificial | 4-OH | C3H5 | CH3 | 4-hydroxy-N-cyclopropyl-N-methyltryptamine | 2883663-05-4 |
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4-HO-McPeT | artificial | 4-OH | C5H9 | CH3 | 4-hydroxy-N-cyclopentyl-N-methyltryptamine | 77872-48-1 |
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4-HO-McPMT [8] | artificial | 4-OH | CH2C3H5 | CH3 | 4-hydroxy-N-cyclopropylmethyl-N-methyltryptamine | |
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4-HO-DPT | artificial | 4-OH | CH2CH2CH3 | CH2CH2CH3 | 4-hydroxy-N,N-dipropyltryptamine | 63065-88-3 |
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4-AcO-DPT | artificial | 4-OCOCH3 | CH2CH2CH3 | CH2CH2CH3 | 4-acetoxy-N,N-dipropyltryptamine | 1445751-75-6 |
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4-HO-PiPT | artificial | 4-OH | CH2CH2CH3 | CH(CH3)2 | 4-hydroxy-N-propyl-N-isopropyltryptamine | |
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4-AcO-PiPT | artificial | 4-OCOCH3 | CH2CH2CH3 | CH(CH3)2 | 4-acetoxy-N-propyl-N-isopropyltryptamine | |
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4-HO-DIPT | artificial | 4-OH | CH(CH3)2 | CH(CH3)2 | 4-hydroxy-N,N-diisopropyltryptamine | 132328-45-1 |
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4-Acetoxy-DiPT | artificial | 4-OCOCH3 | CH(CH3)2 | CH(CH3)2 | 4-acetoxy-N,N-diisopropyltryptamine | 936015-60-0 |
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4-PrO-DiPT | artificial | 4-OCOCH2CH3 | CH(CH3)2 | CH(CH3)2 | 4-propionyloxy-N,N-diisopropyltryptamine | 1373882-13-3 |
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FT-104 | artificial | 4-OCO(CH2)3COOH | CH(CH3)2 | CH(CH3)2 | 4-glutaryloxy-N,N-diisopropyltryptamine | |
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4-PO-DiPT | artificial | 4-OPO3H2 | CH(CH3)2 | CH(CH3)2 | 4-phosphoryloxy-N,N-diisopropyltryptamine | 1373882-09-7 |
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4-HO-DALT | artificial | 4-OH | H2C=CH-CH2 | H2C=CH-CH2 | 4-hydroxy-N,N-diallyltryptamine | |
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4-AcO-DALT | artificial | 4-OCOCH3 | H2C=CH-CH2 | H2C=CH-CH2 | 4-acetoxy-N,N-diallyltryptamine | 1445751-71-2 |
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4-HO-DBT | artificial | 4-OH | (CH2)3CH3 | (CH2)3CH3 | 4-hydroxy-N,N-dibutyltryptamine | 63065-89-4 |
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4-HO-DIBT | artificial | 4-OH | CH2CH(CH3)2 | CH2CH(CH3)2 | 4-hydroxy-N,N-diisobutyltryptamine | |
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4-HO-DSBT | artificial | 4-OH | CH(CH3)CH2CH3 | CH(CH3)CH2CH3 | 4-hydroxy-N,N-disecbutyltryptamine | 127507-01-1 |
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5-MeO-MET | artificial | 5-OCH3 | CH2CH3 | CH3 | 5-methoxy-N-Methyl-N-ethyltryptamine | 16977-53-0 |
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5-MeO-DET | artificial | 5-OCH3 | CH2CH3 | CH2CH3 | 5-methoxy-N,N-diethyltryptamine | 2454-70-8 |
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5-MeO-MPT | artificial | 5-OCH3 | CH3 | CH2CH2CH3 | 5-methoxy-N-methyl-N-propyltryptamine | |
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5-MeO-EPT | artificial | 5-OCH3 | CH2CH3 | CH2CH2CH3 | 5-methoxy-N-ethyl-N-propyltryptamine | 850032-67-6 |
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5-MeO-DPT | artificial | 5-OCH3 | CH2CH2CH3 | CH2CH2CH3 | 5-methoxy-N,N-dipropyltryptamine | 69496-75-9 |
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5-MeO-MALT | artificial | 5-OCH3 | H2C=CH-CH2 | CH3 | 5-methoxy-N-Methyl-N-allyltryptamine | 1373918-64-9 |
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5-MeO-DALT | artificial | 5-OCH3 | H2C=CH-CH2 | H2C=CH-CH2 | 5-methoxy-N,N-diallyltryptamine | 928822-98-4 |
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5-MeO-ALiPT | artificial | 5-OCH3 | H2C=CH-CH2 | CH2CH(CH3)2 | 5-methoxy-N-allyl-N-isopropyltryptamine | |
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5-MeO-MiPT | artificial | 5-OCH3 | CH3 | CH(CH3)2 | 5-methoxy-N,N-methylisopropyltryptamine | 96096-55-8 |
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5,6-MeO-MiPT | artificial | 5-OCH3, 6-OCH3 | CH3 | CH(CH3)2 | 5,6-dimethoxy-N,N-methylisopropyltryptamine | |
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5-MeO-McPT | artificial | 5-OCH3 | CH3 | C3H5 | 5-methoxy-N-methyl-N-cyclopropyltryptamine | |
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5-MeO-McBT | artificial | 5-OCH3 | CH3 | C4H7 | 5-methoxy-N-methyl-N-cyclobutyltryptamine | |
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5-MeO-EiPT | artificial | 5-OCH3 | CH2CH3 | CH(CH3)2 | 5-methoxy-N-ethyl-N-isopropyltryptamine | 850032-66-5 |
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5-MeO-PiPT | artificial | 5-OCH3 | CH2CH2CH3 | CH(CH3)2 | 5-methoxy-N-propyl-N-isopropyltryptamine | |
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5-MeO-DIPT | artificial | 5-OCH3 | CH(CH3)2 | CH(CH3)2 | 5-methoxy-N,N-diisopropyltryptamine | 4021-34-5 |
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5-MeO-DBT | artificial | 5-OCH3 | (CH2)3CH3 | (CH2)3CH3 | 5-methoxy-N,N-dibutyltryptamine | 73785-42-9 |
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5-MeO-DSBT | artificial | 5-OCH3 | CH(CH3)CH2CH3 | CH(CH3)CH2CH3 | 5-methoxy-N,N-di-sec-butyltryptamine | |
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5-MeS-DMT | artificial | 5-SCH3 | CH3 | CH3 | 5-methylthio-N,N-dimethyltryptamine | 5102-11-4 |
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5-AcO-DMT | artificial | 5-OCOCH3 | CH3 | CH3 | 5-acetoxy-N,N-dimethyltryptamine | 16977-50-7 |
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5-AcO-MET [9] | artificial | 5-OCOCH3 | CH3 | CH2CH3 | 5-acetoxy-N-methyl-N-ethyltryptamine | |
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5-AcO-DET | artificial | 5-OCOCH3 | CH2CH3 | CH2CH3 | 5-acetoxy-N,N-diethyltryptamine | |
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5-AcO-EPT [10] | artificial | 5-OCOCH3 | CH2CH3 | CH2CH2CH3 | 5-acetoxy-N-ethyl-N-propyltryptamine | |
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5-AcO-DPT | artificial | 5-OCOCH3 | CH2CH2CH3 | CH2CH2CH3 | 5-acetoxy-N,N-dipropyltryptamine | |
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5-AcO-MiPT | artificial | 5-OCOCH3 | CH3 | CH(CH3)2 | 5-acetoxy-N-methyl-N-isopropyltryptamine | |
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5-AcO-DiPT | artificial | 5-OCOCH3 | CH(CH3)2 | CH(CH3)2 | 5-acetoxy-N,N-diisopropyltryptamine | |
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5-Ethoxy-DMT | artificial | 5-OCH2CH3 | CH3 | CH3 | 5-ethoxy-N,N-dimethyltryptamine | 855245-09-9 |
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5-Ethoxy-MET | artificial | 5-OCH2CH3 | CH3 | CH2CH3 | 5-ethoxy-N-methyl-N-ethyltryptamine | |
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5-Ethoxy-DET | artificial | 5-OCH2CH3 | CH2CH3 | CH2CH3 | 5-ethoxy-N,N-diethyltryptamine | |
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5-Ethoxy-MPT | artificial | 5-OCH2CH3 | CH3 | CH2CH2CH3 | 5-ethoxy-N-methyl-N-propyltryptamine | |
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5-Ethoxy-EPT | artificial | 5-OCH2CH3 | CH2CH3 | CH2CH2CH3 | 5-ethoxy-N-ethyl-N-propyltryptamine | |
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5-Ethoxy-DPT | artificial | 5-OCH2CH3 | CH2CH2CH3 | CH2CH3 | 5-ethoxy-N,N-dipropyltryptamine | |
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5-Ethoxy-MiPT | artificial | 5-OCH2CH3 | CH3 | CH(CH3)2 | 5-ethoxy-N-methyl-N-isopropyltryptamine | |
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5-Ethoxy-EiPT | artificial | 5-OCH2CH3 | CH2CH3 | CH(CH3)2 | 5-ethoxy-N-ethyl-N-isopropyltryptamine | |
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5-Ethoxy-DiPT | artificial | 5-OCH2CH3 | CH(CH3)2 | CH(CH3)2 | 5-ethoxy-N,N-diisopropyltryptamine | |
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5-Ethoxy-DALT | artificial | 5-OCH2CH3 | H2C=CH-CH2 | H2C=CH-CH2 | 5-ethoxy-N,N-diallyltryptamine | |
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5-BnO-DMT | artificial | 5-OCH2C6H5 | CH3 | CH3 | 5-benzyloxy-N,N-dimethyltryptamine | 101832-88-6 |
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5-HO-DET | artificial | 5-OH | CH2CH3 | CH2CH3 | 5-hydroxy-N,N-diethyltryptamine | 14009-42-8 |
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5-HO-DPT | artificial | 5-OH | CH2CH2CH3 | CH2CH2CH3 | 5-hydroxy-N,N-dipropyltryptamine | 36288-75-2 |
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5-HO-MiPT | artificial | 5-OH | CH3 | CH(CH3)2 | 5-hydroxy-N-methyl-N-isopropyltryptamine | |
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5-HO-DiPT | artificial | 5-OH | CH(CH3)2 | CH(CH3)2 | 5-hydroxy-N,N-diisopropyltryptamine | 36288-76-3 |
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5-Methyl-DMT (5,N,N-TMT) | artificial | 5-CH3 | CH3 | CH3 | 5,N,N-trimethyltryptamine | 22120-39-4 |
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5-Ethyl-DMT | artificial | 5-CH2CH3 | CH3 | CH3 | 5-ethyl-N,N-dimethyltryptamine | 171783-25-8 |
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5-Isopropyl-DMT | artificial | 5-CH(CH3)2 | CH3 | CH3 | 5-isopropyl-N,N-dimethyltryptamine | 156281-04-8 |
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5-(t-Butyl)-DMT [11] | artificial | 5-C(CH3)3 | CH3 | CH3 | 5-(tert-butyl)-N,N-dimethyltryptamine | |
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5-Fluoro-DMT | artificial | 5-F | CH3 | CH3 | 5-fluoro-N,N-dimethyltryptamine | 22120-36-1 |
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5-Fluoro-MET | artificial | 5-F | CH3 | CH2CH3 | 5-fluoro-N-methyl-N-ethyltryptamine | |
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5-Fluoro-DET | artificial | 5-F | CH2CH3 | CH2CH3 | 5-fluoro-N,N-diethyltryptamine | |
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5-Fluoro-EPT | artificial | 5-F | CH2CH3 | CH2CH2CH3 | 5-fluoro-N-ethyl-N-propyltryptamine | |
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5-Fluoro-DPT | artificial | 5-F | CH2CH2CH3 | CH2CH2CH3 | 5-fluoro-N,N-dipropyltryptamine | |
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5-Fluoro-PiPT | artificial | 5-F | CH2CH2CH3 | CH(CH3)2 | 5-fluoro-N-propyl-N-isopropyltryptamine | |
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5-Fluoro-PcBT | artificial | 5-F | CH2CH2CH3 | CH(CH2)3 | 5-fluoro-N-propyl-N-cyclobutyltryptamine | |
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5-Fluoro-iPcBT | artificial | 5-F | CH(CH3)2 | CH(CH2)3 | 5-fluoro-N-isopropyl-N-cyclobutyltryptamine | |
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5-Fluoro-DiPT | artificial | 5-F | CH(CH3)2 | CH(CH3)2 | 5-fluoro-N,N-diisoproptryptamine | |
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5-Fluoro-sBALT | artificial | 5-F | CH(CH3)CH2CH3 | CH2CH=CH2 | 5-fluoro-N-sec-butyl-N-allyltryptamine | |
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5-Fluoro-M1MALT | artificial | 5-F | CH3 | CH(CH3)CH=CH2 | 5-fluoro-N-methyl-N-(1-methylallyl)tryptamine | |
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5-Chloro-DMT | artificial | 5-Cl | CH3 | CH3 | 5-chloro-N,N-dimethyltryptamine | 22120-32-7 |
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5-Iodo-DMT | artificial | 5-I | CH3 | CH3 | 5-iodo-N,N-dimethyltryptamine | 22120-38-3 |
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5-TFM-DMT | artificial | 5-CF3 | CH3 | CH3 | 5-(trifluoromethyl)-N,N-dimethyltryptamine | 2418713-32-1 |
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5-TFMO-DMT[12] | artificial | 5-OCF3 | CH3 | CH3 | 5-(trifluoromethoxy)-N,N-dimethyltryptamine | |
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5-Nitro-DMT[13] | artificial | 5-NO2 | CH3 | CH3 | 5-nitro-N,N-dimethyltryptamine | 69937-13-9 |
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5-CN-DMT | artificial | 5-C≡N | CH3 | CH3 | 5-cyano-N,N-dimethyltryptamine | 17380-42-6 |
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5-CN-DPT | artificial | 5-C≡N | CH2CH2CH3 | CH2CH2CH3 | 5-cyano-N,N-dipropyltryptamine | 74885-19-1 |
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Almotriptan | artificial | 5-(CH2SO2N(CH2)4) | CH3 | CH3 | N,N-dimethyl-2- [5-(pyrrolidin-1-ylsulfonylmethyl)- 1H-indol-3-yl]-ethanamine | 154323-57-6 |
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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 |
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Sumatriptan | artificial | 5-(CH2SO2NHCH3) | CH3 | CH3 | 1-[3-(2-Dimethylaminoethyl)-1H-indol-5-yl]-N-methyl-methanesulfonamide | 103628-46-2 |
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Zolmitriptan | artificial | 5-(CHNHC=OOCH2) | CH3 | CH3 | 5-( 4-(S)-1,3-oxazolidin-2-one)-N,N-dimethyltryptamine | 139264-17-8 |
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6-Fluoro-DMT | artificial | 6-F | CH3 | CH3 | 6-fluoro-N,N-dimethyltryptamine | 1511-31-5 |
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6-Fluoro-DET[14] | artificial | 6-F | CH2CH3 | CH2CH3 | 6-fluoro-N,N-diethyltryptamine | 2836-69-3 |
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6-Chloro-DMT | artificial | 6-Cl | CH3 | CH3 | 6-chloro-N,N-dimethyltryptamine | 25390-72-1 |
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6-Methyl-DMT | artificial | 6-CH3 | CH3 | CH3 | 6,N,N-trimethyltryptamine | |
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6-Hydroxy-DMT | artificial | 6-OH | CH3 | CH3 | 6-hydroxy-N,N-dimethyltryptamine | 1476-33-1 |
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6-Hydroxy-DET | artificial | 6-OH | CH3 | CH3 | 6-hydroxy-N,N-diethyltryptamine | 1476-59-1 |
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6-Methoxy-DMT | artificial | 6-OCH3 | CH3 | CH3 | 6-methoxy-N,N-dimethyltryptamine | 2426-88-2 |
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7-Methyl-DMT | artificial | 7-CH3 | CH3 | CH3 | 7,N,N-trimethyltryptamine | 65882-39-5 |
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7-Ethyl-DMT | artificial | 7-CH2CH3 | CH3 | CH3 | 7-ethyl-N,N-dimethyltryptamine | |
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7-Chloro-DMT | artificial | 7-Cl | CH3 | CH3 | 7-chloro-N,N-dimethyltryptamine | |
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7-Bromo-DMT[15] | artificial | 7-Br | CH3 | CH3 | 7-bromo-N,N-dimethyltryptamine | 74798-68-8 |
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7-Methoxy-DMT | artificial | 7-OCH3 | CH3 | CH3 | 7-methoxy-N,N-dimethyltryptamine | |
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7-Methoxy-MiPT | artificial | 7-OCH3 | CH3 | CH(CH3)2 | 7-methoxy-N-methyl-N-isopropyltryptamine | |
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1-Methylpsilocin | artificial | 1-CH3, 4-OH | CH3 | CH3 | 1-Methyl-3-[2-(N,N-dimethylamino)ethyl]-4-hydroxyindole | 1465-16-3 |
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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 |
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NB-5-MeO-MiPT | artificial | 1-OCOC(CH3)3, 5-OCH3 | CH3 | CH(CH3)2 | 1-(t-butoxycarbonyl)-5-methoxy-N-methyl-N-isopropyltryptamine | |
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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 | |
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6-Fluoropsilocin | artificial | 4-OH,6-F | CH3 | CH3 | 4-hydroxy-6-fluoro-N,N-dimethyltryptamine | 312314-12-8 |
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6-Fluoro-5-MeO-DMT | artificial | 5-OCH3,6-F | CH3 | CH3 | 5-methoxy-6-fluoro-N,N-dimethyltryptamine | |
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5,6-Difluoro-EPT | artificial | 5-F, 6-F | CH2CH3 | CH2CH2CH3 | 5,6-difluoro-N-ethyl-N-propyltryptamine | |
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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 |
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5-Methoxy-7,N,N-trimethyltryptamine | artificial | 5-OCH3, 7-CH3 | CH3 | CH3 | 5-Methoxy-7,N,N-trimethyltryptamine | 61018-77-7 |
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5-Methoxy-4,N,N-trimethyltryptamine | artificial | 4-CH3, 5-OCH3 | CH3 | CH3 | 5-Methoxy-4,N,N-trimethyltryptamine | |
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4-HO-5-MeO-DMT | artificial | 4-OH, 5-OCH3 | CH3 | CH3 | 4-Hydroxy-5-methoxy-N,N-dimethyltryptamine | 2433-31-0 |
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4-F-5-MeO-DMT | artificial | 4-F, 5-OCH3 | CH3 | CH3 | 4-Fluoro-5-Methoxy-N,N-dimethyltryptamine | 312314-18-4 |
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5-methoxy-7-fluoro-MET | artificial | 5-OCH3, 7-F | CH3 | CH2CH3 | 5-Methoxy-7-Fluoro-N-methyl-N-ethyltryptamine | |
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EMDT | artificial | 2-CH2CH3, 5-OCH3 | CH3 | CH3 | 2-(2-ethyl-5-methoxy-1H-indol-3-yl)-N,N-dimethylethanamine | 263744-72-5 |
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ST-1936 | artificial | 2-CH3, 5-Cl | CH3 | CH3 | 2-(2-methyl-5-chloro-1H-indol-3-yl)-N,N-dimethylethanamine | 1210-81-7 |
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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 |
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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 |
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4,5-DHP-DMT | artificial | 4,5-(OCH2CH2CH2) | CH3 | CH3 | 1-(2-dimethylaminoethyl)-8,9-dihydropyrano[3,2-e]indole | 135360-97-3 |
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4,5-DHF-DMT (P-3) | artificial[16] | 4,5-(CH2CH2O) | CH3 | CH3 | 2-(3,6-dihydro-2H-furo[2,3-e]indol-8-yl)-N,N-dimethylethan-1-amine | |
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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 | |
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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 |
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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 |
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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 | |
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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 | |
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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 | |
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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.[17][18][19] 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.[19] This is analogous to α-methylation of phenethylamine into amphetamine.[19]
Many α-alkyltryptamines are drugs, acting as monoamine releasing agents, non-selective serotonin receptor agonists, and/or monoamine oxidase inhibitors,[20][21][22][23] and produce psychostimulant, entactogen, and/or psychedelic effects.[17][18][19] 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.[18][19] 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.[24]
Structure | Common name | Chemical name | CAS number |
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Tryptophan | (2S)-2-amino-3-(1H-indol-3-yl)propanoic acid | 73-22-3 |
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5-Hydroxytryptophan | 2-amino-3-(5-hydroxy-1H-indol-3-yl)propanoic acid | 4350-09-8 |
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αMT | 1-(1H-Indol-3-yl)propan-2-amine | 299-26-3 |
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4-HO-αMT | 3-(2-aminopropyl)-1H-indol-4-ol | 15066-09-8 |
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4-Methyl-αMT | 1-methyl-2-(4-methyl-1H-indol-3-yl)-ethylamine | 3569-29-7 |
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5-Fluoro-αMT | 1-(5-fluoro-1H-indol-3-yl)propan-2-amine | 712-08-3 |
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5-Chloro-αMT | 1-(5-Chloro-1H-indol-3-yl)propan-2-amine | 712-07-2 |
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5-HO-αMT (αMS/α-methyl-5-HT) | 3-(2-aminopropyl)-1H-indol-5-ol | 304-52-9 |
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5-MeO-αMT | 1-(5-methoxy-1H-indol-3-yl)propan-2-amine | 1137-04-8 |
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5-Ethoxy-αMT | 1-(5-ethoxy-1H-indol-3-yl)propan-2-amine | 101832-83-1 |
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5-Isopropoxy-αMT | 1-{5-[(propan-2-yl)oxy]-1H-indol-3-yl}propan-2-amine | |
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BW-723C86 | 1-[5-(2-Thienylmethoxy)-1H-indol-3-yl]-2-propanamine | 160521-72-2 |
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6-Fluoro-αMT | 1-(6-fluoro-1H-indol-3-yl)propan-2-amine | 712-11-8 |
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7-Chloro-AMT | 1-(7-chloro-1H-indol-3-yl)propan-2-amine | 711-99-9 |
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AL-37350A (4,5-dihydropyrano-αMT) | (S)-(+)-1-(2-Aminopropyl)-8,9-dihydropyrano[3,2-e]indole | 362603-40-5 |
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Compound 5 [25] | 1-(3H-benzo[e]indol-1-yl)propan-2-amine | |
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αET | 1-(1H-indol-3-yl)butan-2-amine | 2235-90-7 |
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4-Methyl-αET | 1-(4-Methyl-1H-indol-3-yl)butan-2-amine | 28289-30-7 |
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4-HO-αET | 1-(4-hydroxy-1H-indol-3-yl)butan-2-amine | 28289-28-3 |
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5-Fluoro-αET | 1-(5-fluoro-1H-indol-3-yl)butan-2-amine | 1380137-98-3 |
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5-Methyl-αET | 1-(5-methyl-1H-indol-3-yl)butan-2-amine | 1380148-21-9 |
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5-MeO-αET | 1-(5-methoxy-1H-indol-3-yl)butan-2-amine | 4765-10-0 |
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7-Methyl-αET | 1-(7-methyl-1H-indol-3-yl)butan-2-amine | 13712-80-6 |
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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 |
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N,N-Dimethyl-αMT (α,N,N-TMT) | (2-(1H-Indol-3-yl)-1-methyl-ethyl)dimethylamine | 4761-32-4 |
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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 |
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αMDiPT | (2-(1H-Indol-3-yl)-1-methyl-ethyl)diisopropylamine | |
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MPMI[26] | 3-[(1-methylpyrrolidin-2-yl)methyl]-1H-indole | 143321-54-4 |
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Lucigenol | (R)-3-(N-methylpyrrolidin-2-ylmethyl)-4-hydoxyindole | 250672-65-2 |
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5-MeO-MPMI | 5-Methoxy-3-{[(2R)-1-methylpyrrolidin-2-yl]methyl}-1H-indole | 143321-57-7 |
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5F-MPMI[27] | (R)-5-fluoro-3-[(1-methylpyrrolidin-2-yl)methyl]-1H-indole | |
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5-Br-MPMI | 5-bromo-3-[(1-methylpyrrolidin-2-yl)methyl]-1H-indole | 143322-57-0 |
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Eletriptan | 3-{[(2R)-1-methylpyrrolidin-2-yl]methyl}-5-[2-(benzenesulfonyl)ethyl]-1H-indole | 143322-58-1 |
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 |
---|---|---|---|
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Dimemebfe | 2-(5-Methoxy-1-benzofuran-3-yl)-N,N-dimethylethanamine | 140853-58-3 |
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5-MeO-DiBF | N-[2-(5-Methoxy-1-benzofuran-3-yl)ethyl]-N-(propan-2-yl)propan-2-amine | |
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3-APB | 3-(2-aminopropyl)benzofuran | 105909-13-5 |
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Mebfap | 3-(2-aminopropyl)-5-methoxybenzofuran | 140853-59-4 |
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Ro60-0175 | (S)-(6-chloro-5-fluoro-1H-indol-1-yl)propan-2-amine | 169675-09-6 |
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AAZ-A-154 | (2R)-1-(5-methoxy-1H-indol-1-yl)-N,N-dimethylpropan-2-amine | |
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Example 1 [28] | 1-(3-methyl-8,9-dihydropyrano[2,3-g]indol-1(7H)-yl)propan-2-amine | |
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VER-3323 | (2S)-1-(6-bromo-2,3-dihydroindol-1-yl)propan-2-amine | 259857-99-3 |
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AL-34662 | 1-((S)-2-Aminopropyl)-1H-indazol-6-ol | 210580-75-9 |
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O-methyl-AL-34662 | 1-((S)-6-methoxy-2-aminopropyl)-1H-indazole | 210580-60-2 |
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7-methyl-AL-34662 | 1-((S)-2-Aminopropyl)-7-methyl-1H-indazol-6-ol | 874668-67-4 |
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7-chloro-AL-34662 | 1-((S)-2-Aminopropyl)-7-chloro-1H-indazol-6-ol | 874881-86-4 |
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AL-38022A | (S)-2-(8,9-dihydro-7H-pyrano[2,3-g]indazol-1-yl)-1-methylethylamine | 478132-11-5 |
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Example 9 [29] | (S)-α-methyl-pyrano[2,3-g]indazole-1(7H)-ethanamine | 478132-12-6 |
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Example 3 [30] | (S)-7,8-dihydro-α-methyl-1H-[1,4]dioxino[2,3-g]indazole-1-ethanamine | 890087-75-9 |
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Example 1 [31] | (S)-8,9-dihydro-α,9-dimethylpyrazolo[3,4-f][1,4]benzoxazine-1(7H)-ethanamine | 1373917-69-1 |
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YM-348 | (2S)-1-(7-ethyl-1H-furo[2,3-g]indazol-1-yl)propan-2-amine | 372163-84-3 |
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2-desethyl-YM-348 [32] | (2S)-1-(1H-furo[2,3-g]indazol-1-yl)propan-2-amine | 748116-94-1 |
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I-32 [33] | 3-(1-methylpyrrolidin-3-yl)-1H-indol-4-ol | |
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2-Azapsilocin (Psilocin indazole analogue, P-6)[34] | 3-[2-(dimethylamino)ethyl]-1H-indazol-4-ol | |
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4-Aza-5-MeO-DPT (P-11) | N-[2-(5-methoxy-1H-pyrrolo[3,2-b]pyridin-3-yl)ethyl]-N-propylpropan-1-amine | |
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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 | |
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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 | |
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(R)-69 | 3-[(5R)-5-methyl-1,2,5,6-tetrahydropyridin-3-yl]-1H-pyrrolo[2,3-b]pyridine | |
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SN-22 | 3-(1-methylpiperidin-4-yl)-1H-indole | 17403-07-5 |