{"Abbreviation":"αMT","Aliases":["α-Methyltryptamine","Indopan","α-Methyl-β-indoleethylamine","1-(1H-Indol-3-yl)-2-propanamine","α-Methyl-1H-indole-3-ethanamine","α-Methyl-3-indoleethanamine","Indole, 3-(2-aminopropyl)-","Ro 3-0926","αMT","1H-Indole-3-ethanamine, α-methyl-","164 E","206-073-7","3-(2-Aminopropyl)indole","IT-403(D)","U 14164 E","α-Methyl-β-indolaethylamine","It-290(d,l)","U-14164e(d,l)","SPIRALS","164E","U 14","It-290(dl)","2-(1H-indol-3-yl)-1-methylethylamine","u-14164e(dl)","α-Methyltryptamine-"],"CAS":"299-26-3","ChEBI":"CHEBI:59020","ChEMBL":"CHEMBL30713","ChemicalClasses":["α-alkyltryptamine"],"Chirality":"racemic","Classes":["Psychedelic"],"DEA no":7432,"EINECS":"206-073-7","Erowid Experience Reports":[],"Esters":[],"European Community (EC) Number":"206-073-7","Formating":["alpha-methyltryptamine"],"HMDB ID":"HMDB0245770","HeavyAtomCount":13,"IUPACName":"1-(1H-indol-3-yl)propan-2-amine","InChI":"InChI=1S/C11H14N2/c1-8(12)6-9-7-13-11-5-3-2-4-10(9)11/h2-5,7-8,13H,6,12H2,1H3","InChIKey":"QSQQQURBVYWZKJ-UHFFFAOYSA-N","Melting Point":"98-100 °C","MolecularFormula":"C\u003csub\u003e11\u003c/sub\u003eH\u003csub\u003e14\u003c/sub\u003eN\u003csub\u003e2\u003c/sub\u003e","MolecularWeight":"174.24 g/mol","Opticalactivity":"( + / - )","Pharmacodynamics":"With 20-30 milligrams, euphoria, empathy and psychedelic effects are noticeable. Side effects reported have included anxiety, restlessness, tachycardia, muscle tension, jaw tightness, headache, nausea, vomiting, and pupil dilation.","PubChemId":9287,"Record Description":["\u0026#945;-Methyltryptamine (abbreviated as \u0026#945;MT, AMT) is a psychedelic, stimulant, and entactogen drug of the tryptamine class. It was originally developed as an antidepressant by workers at Upjohn in the 1960s,[4] and was used briefly as an antidepressant in Russia under the trade name Indopan before being discontinued. \u0026#945;MT has been shown as a reversible inhibitor of the enzyme monoamine oxidase (MAO) in-vitro and in-vivo. In rats the potency of \u0026#945;MT as an MAO-A inhibitor in the brain was approximately equal to that of harmaline at equimolar doses.[note 1] Dexamphetamine did not enhance the 5-hydroxytryptophan-induced rise of serotonin at any level.","Wikipedia|TiHKAL|Tryptamines","Wikipedia|List of designer drugs|Empathogens|Tryptamines"],"RefCount":3,"RefCur":"","References":[{"Name":"Wikipedia","Urls":[{"Link":"https://en.wikipedia.org/wiki/α-Methyltryptamine","Name":"α-Methyltryptamine","Sub":false}]},{"Name":"DrugBank","Urls":[{"Link":"https://go.drugbank.com/drugs/DB01446","Name":"α-Methyltryptamine","Sub":false}]},{"Name":"PubChem","Urls":[{"Link":"https://pubchem.ncbi.nlm.nih.gov/compound/9287","Name":"α-Methyltryptamine","Sub":false}]},{"Name":"ChEMBL","Urls":[{"Link":"https://www.ebi.ac.uk/chembl/explore/compound/CHEMBL30713","Name":"α-Methyltryptamine","Sub":false}]},{"Name":"ChEBI","Urls":[{"Link":"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:59020","Name":"α-Methyltryptamine","Sub":false}]},{"Name":"Common Chemistry","Urls":[{"Link":"https://commonchemistry.cas.org/detail?cas_rn=299-26-3","Name":"α-Methyltryptamine","Sub":false}]},{"Name":"HMDB","Urls":[{"Link":"https://hmdb.ca/metabolites/HMDB0245770","Name":"α-Methyltryptamine","Sub":false}]},{"Name":"KEGG","Urls":[{"Link":"https://www.kegg.jp/entry/C20127","Name":"α-Methyltryptamine","Sub":false}]},{"Name":"UNII","Urls":[{"Link":"https://gsrs.ncats.nih.gov/ginas/app/ui/substances/BIK35ACJ0Q","Name":"α-Methyltryptamine","Sub":false}]},{"Name":"EPA DSSTox","Urls":[{"Link":"https://comptox.epa.gov/dashboard/chemical/details/DTXSID00861850","Name":"α-Methyltryptamine","Sub":false}]}],"Refs":["National Center for Biotechnology Information. PubChem Compound Summary for CID 9287, α-Methyltryptamine. Accessed July 14, 2025. \u003ca href=https://pubchem.ncbi.nlm.nih.gov/compound/9287\u003ehttps://pubchem.ncbi.nlm.nih.gov/compound/9287\u003c/a\u003e","U.S. Food and Drug Administration; National Center for Advancing Translational Sciences. α-Methyltryptamine. UNII: BIK35ACJ0Q. Global Substance Registration System. Accessed July 14, 2025. \u003ca href=https://gsrs.ncats.nih.gov/ginas/app/beta/substances/BIK35ACJ0Q\u003ehttps://gsrs.ncats.nih.gov/ginas/app/beta/substances/BIK35ACJ0Q\u003c/a\u003e"],"SMILES":"CC(CC1=CNC2=CC=CC=C21)N","SaltData":[],"Salts":[],"Slang":["Spirals "],"StereoisomerData":[{"Aliases":null,"PubChemId":null,"SMILES":"C[C@@H](N)Cc1c[nH]c2ccccc12","Structure":"\u003csvg xmlns=\"http://www.w3.org/2000/svg\" preserveAspectRatio=\"none\" style=\"display:block\" viewBox=\"0 0 93.723 46.26\"\u003e\u003crect width=\"100%\" height=\"100%\" fill=\"#fff\"/\u003e\u003cdesc\u003eGenerated by the Chemistry Development Kit (http://github.com/cdk)\u003c/desc\u003e\u003cg fill=\"#3050f8\" stroke=\"#000\" stroke-linecap=\"round\" stroke-linejoin=\"round\" stroke-width=\".7\"\u003e\u003cpath fill=\"#fff\" stroke=\"none\" d=\"M0 0h94v47H0z\"/\u003e\u003cg class=\"mol\"\u003e\u003cg class=\"bond\"\u003e\u003cpath d=\"M71.554 25.011h-.701M71.842 27.552l-1.283-.002M72.131 30.092l-1.867-.002M72.419 32.633l-2.45-.003M72.708 35.173l-3.034-.004M72.996 37.713l-3.617-.004M73.285 40.254l-4.2-.006\"/\u003e\u003c/g\u003e\u003cpath d=\"m71.204 25.011 10.053-5.788M71.204 25.011l-13.189-7.636M58.015 17.375l-13.208 7.604\" class=\"bond\"/\u003e\u003cg class=\"bond\"\u003e\u003cpath d=\"m43.225 40.097 1.582-15.118M40.985 38.08l1.213-11.599\"/\u003e\u003c/g\u003e\u003cpath d=\"m43.225 40.097-11.56 2.451M26.227 39.59l-5.542-9.534\" class=\"bond\"/\u003e\u003cg class=\"bond\"\u003e\u003cpath d=\"m5.771 26.881 14.914 3.175M7.655 24.788l12.161 2.589\"/\u003e\u003c/g\u003e\u003cpath d=\"M5.771 26.881 1.054 12.38\" class=\"bond\"/\u003e\u003cg class=\"bond\"\u003e\u003cpath d=\"M11.252 1.054 1.054 12.38M12.122 3.733l-8.313 9.232\"/\u003e\u003c/g\u003e\u003cpath d=\"m11.252 1.054 14.914 3.175\" class=\"bond\"/\u003e\u003cg class=\"bond\"\u003e\u003cpath d=\"M30.883 18.73 26.166 4.229M28.128 18.145 24.282 6.321\"/\u003e\u003c/g\u003e\u003cpath d=\"M44.807 24.979 30.883 18.73M20.685 30.056 30.883 18.73\" class=\"bond\"/\u003e\u003cg stroke=\"none\" class=\"atom\"\u003e\u003cpath d=\"M86.352 19.857h-.721l-2.619-4.066h-.03l.03.595q.024.357.024.733v2.738h-.566v-4.899h.715l2.607 4.054h.03l-.018-.328-.024-.476q-.006-.262-.006-.482v-2.768h.578zM90.658 19.857h-.619v-2.286h-2.512v2.286h-.614v-4.899h.614v2.071h2.512v-2.071h.619zM93.163 21.346H91.22v-.3l.771-.778q.222-.222.372-.393.153-.175.232-.339.078-.168.078-.365 0-.243-.146-.368-.143-.128-.371-.128-.215 0-.379.075-.161.075-.329.207l-.193-.243q.172-.146.393-.246.225-.101.508-.101.41 0 .65.208.239.207.239.575 0 .228-.097.432-.092.2-.264.396-.168.197-.393.418l-.614.604v.018h1.486z\"/\u003e\u003c/g\u003e\u003cg stroke=\"none\" class=\"atom\"\u003e\u003cpath d=\"M30.296 45.7h-.721l-2.619-4.066h-.03l.03.596q.024.357.024.732V45.7h-.566v-4.899h.715l2.607 4.054h.03l-.018-.328-.024-.476q-.006-.262-.006-.482v-2.768h.578zM25.853 45.7h-.619v-2.286h-2.513V45.7h-.613v-4.899h.613v2.071h2.513v-2.071h.619z\"/\u003e\u003c/g\u003e\u003cpath stroke=\"#3050f8\" d=\"m81.257 19.223-5.026 2.894M31.665 42.548l5.78-1.225M31.665 42.548l5.78-1.225M26.227 39.59l-2.771-4.767M26.227 39.59l-2.771-4.767\" class=\"hi\"/\u003e\u003c/g\u003e\u003c/g\u003e\u003c/svg\u003e","Title":"(R)-α-Methyltryptamine","UNII":null},{"Aliases":null,"PubChemId":null,"SMILES":"C[C@H](N)Cc1c[nH]c2ccccc12","Structure":"\u003csvg xmlns=\"http://www.w3.org/2000/svg\" preserveAspectRatio=\"none\" style=\"display:block\" viewBox=\"0 0 93.723 46.26\"\u003e\u003crect width=\"100%\" height=\"100%\" fill=\"#fff\"/\u003e\u003cdesc\u003eGenerated by the Chemistry Development Kit (http://github.com/cdk)\u003c/desc\u003e\u003cg fill=\"#3050f8\" stroke=\"#000\" stroke-linecap=\"round\" stroke-linejoin=\"round\" stroke-width=\".7\"\u003e\u003cpath fill=\"#fff\" stroke=\"none\" d=\"M0 0h94v47H0z\"/\u003e\u003cg class=\"mol\"\u003e\u003cpath fill=\"#000\" stroke=\"none\" d=\"M71.554 25.011h-.701l-1.768 15.237h4.2z\" class=\"bond\"/\u003e\u003cpath d=\"m71.204 25.011 10.053-5.788M71.204 25.011l-13.189-7.636M58.015 17.375l-13.208 7.604\" class=\"bond\"/\u003e\u003cg class=\"bond\"\u003e\u003cpath d=\"m43.225 40.097 1.582-15.118M40.985 38.08l1.213-11.599\"/\u003e\u003c/g\u003e\u003cpath d=\"m43.225 40.097-11.56 2.451M26.227 39.59l-5.542-9.534\" class=\"bond\"/\u003e\u003cg class=\"bond\"\u003e\u003cpath d=\"m5.771 26.881 14.914 3.175M7.655 24.788l12.161 2.589\"/\u003e\u003c/g\u003e\u003cpath d=\"M5.771 26.881 1.054 12.38\" class=\"bond\"/\u003e\u003cg class=\"bond\"\u003e\u003cpath d=\"M11.252 1.054 1.054 12.38M12.122 3.733l-8.313 9.232\"/\u003e\u003c/g\u003e\u003cpath d=\"m11.252 1.054 14.914 3.175\" class=\"bond\"/\u003e\u003cg class=\"bond\"\u003e\u003cpath d=\"M30.883 18.73 26.166 4.229M28.128 18.145 24.282 6.321\"/\u003e\u003c/g\u003e\u003cpath d=\"M44.807 24.979 30.883 18.73M20.685 30.056 30.883 18.73\" class=\"bond\"/\u003e\u003cg stroke=\"none\" class=\"atom\"\u003e\u003cpath d=\"M86.352 19.857h-.721l-2.619-4.066h-.03l.03.595q.024.357.024.733v2.738h-.566v-4.899h.715l2.607 4.054h.03l-.018-.328-.024-.476q-.006-.262-.006-.482v-2.768h.578zM90.658 19.857h-.619v-2.286h-2.512v2.286h-.614v-4.899h.614v2.071h2.512v-2.071h.619zM93.163 21.346H91.22v-.3l.771-.778q.222-.222.372-.393.153-.175.232-.339.078-.168.078-.365 0-.243-.146-.368-.143-.128-.371-.128-.215 0-.379.075-.161.075-.329.207l-.193-.243q.172-.146.393-.246.225-.101.508-.101.41 0 .65.208.239.207.239.575 0 .228-.097.432-.092.2-.264.396-.168.197-.393.418l-.614.604v.018h1.486z\"/\u003e\u003c/g\u003e\u003cg stroke=\"none\" class=\"atom\"\u003e\u003cpath d=\"M30.296 45.7h-.721l-2.619-4.066h-.03l.03.596q.024.357.024.732V45.7h-.566v-4.899h.715l2.607 4.054h.03l-.018-.328-.024-.476q-.006-.262-.006-.482v-2.768h.578zM25.853 45.7h-.619v-2.286h-2.513V45.7h-.613v-4.899h.613v2.071h2.513v-2.071h.619z\"/\u003e\u003c/g\u003e\u003cpath stroke=\"#3050f8\" d=\"m81.257 19.223-5.026 2.894M31.665 42.548l5.78-1.225M31.665 42.548l5.78-1.225M26.227 39.59l-2.771-4.767M26.227 39.59l-2.771-4.767\" class=\"hi\"/\u003e\u003c/g\u003e\u003c/g\u003e\u003c/svg\u003e","Title":"(S)-α-Methyltryptamine","UNII":null}],"StereoisomerType":"enantiomer","Stereoisomers":["(R)-α-Methyltryptamine","(S)-α-Methyltryptamine"],"Structure":"\u003csvg xmlns=\"http://www.w3.org/2000/svg\" preserveAspectRatio=\"none\" style=\"display:block\" viewBox=\"0 0 93.723 46.26\"\u003e\u003crect width=\"100%\" height=\"100%\" fill=\"#fff\"/\u003e\u003cdesc\u003eGenerated by the Chemistry Development Kit (http://github.com/cdk)\u003c/desc\u003e\u003cg fill=\"#3050f8\" stroke=\"#000\" stroke-linecap=\"round\" stroke-linejoin=\"round\" stroke-width=\".7\"\u003e\u003cpath fill=\"#fff\" stroke=\"none\" d=\"M0 0h94v47H0z\"/\u003e\u003cg class=\"mol\"\u003e\u003cpath d=\"m71.185 40.251.019-15.24M71.204 25.011l-13.189-7.636M58.015 17.375l-13.208 7.604\" class=\"bond\"/\u003e\u003cg class=\"bond\"\u003e\u003cpath d=\"m43.225 40.097 1.582-15.118M40.985 38.08l1.213-11.599\"/\u003e\u003c/g\u003e\u003cpath d=\"m43.225 40.097-11.56 2.451M26.227 39.59l-5.542-9.534\" class=\"bond\"/\u003e\u003cg class=\"bond\"\u003e\u003cpath d=\"m5.771 26.881 14.914 3.175M7.655 24.788l12.161 2.589\"/\u003e\u003c/g\u003e\u003cpath d=\"M5.771 26.881 1.054 12.38\" class=\"bond\"/\u003e\u003cg class=\"bond\"\u003e\u003cpath d=\"M11.252 1.054 1.054 12.38M12.122 3.733l-8.313 9.232\"/\u003e\u003c/g\u003e\u003cpath d=\"m11.252 1.054 14.914 3.175\" class=\"bond\"/\u003e\u003cg class=\"bond\"\u003e\u003cpath d=\"M30.883 18.73 26.166 4.229M28.128 18.145 24.282 6.321\"/\u003e\u003c/g\u003e\u003cpath d=\"M20.685 30.056 30.883 18.73M44.807 24.979 30.883 18.73M71.204 25.011l10.053-5.788\" class=\"bond\"/\u003e\u003cg stroke=\"none\" class=\"atom\"\u003e\u003cpath d=\"M30.296 45.7h-.721l-2.619-4.066h-.03l.03.596q.024.357.024.732V45.7h-.566v-4.899h.715l2.607 4.054h.03l-.018-.328-.024-.476q-.006-.262-.006-.482v-2.768h.578zM25.853 45.7h-.619v-2.286h-2.513V45.7h-.613v-4.899h.613v2.071h2.513v-2.071h.619z\"/\u003e\u003c/g\u003e\u003cg stroke=\"none\" class=\"atom\"\u003e\u003cpath d=\"M86.352 19.857h-.721l-2.619-4.066h-.03l.03.595q.024.357.024.733v2.738h-.566v-4.899h.715l2.607 4.054h.03l-.018-.328-.024-.476q-.006-.262-.006-.482v-2.768h.578zM90.658 19.857h-.619v-2.286h-2.512v2.286h-.614v-4.899h.614v2.071h2.512v-2.071h.619zM93.163 21.346H91.22v-.3l.771-.778q.222-.222.372-.393.153-.175.232-.339.078-.168.078-.365 0-.243-.146-.368-.143-.128-.371-.128-.215 0-.379.075-.161.075-.329.207l-.193-.243q.172-.146.393-.246.225-.101.508-.101.41 0 .65.208.239.207.239.575 0 .228-.097.432-.092.2-.264.396-.168.197-.393.418l-.614.604v.018h1.486z\"/\u003e\u003c/g\u003e\u003cpath stroke=\"#3050f8\" d=\"m31.665 42.548 5.78-1.225M31.665 42.548l5.78-1.225M26.227 39.59l-2.771-4.767M26.227 39.59l-2.771-4.767M81.257 19.223l-5.026 2.894\" class=\"hi\"/\u003e\u003c/g\u003e\u003c/g\u003e\u003c/svg\u003e","Subjective Effects":null,"Title":"α-Methyltryptamine","UNII":"BIK35ACJ0Q","Wikipedia":"α-Methyltryptamine","XLogP":2}