{"Abbreviation":["NOHMA","N-OH-MA"],"Aliases":["N-Hydroxy-Methamphetamine","Benzeneethanamine, N-hydroxy-N,α-dimethyl-","N-Hydroxy-N,a-dimethyl-benzeneethanamine","Schembl4282486","N-Hydroxy-N-methyl-1-phenylpropan-2-amine"],"CAS":"52271-36-0","ChemicalClasses":["amphetamine"],"Chirality":"racemic","Classes":["Stimulant"],"DTXSID":"90966646","DurationOfAction":"","EliminationHalfLife":"","Erowid Experience Reports":[],"Esters":[],"Formating":[],"HeavyAtomCount":12,"IUPACName":"N-methyl-N-(1-phenylpropan-2-yl)hydroxylamine","InChI":"InChI=1S/C10H15NO/c1-9(11(2)12)8-10-6-4-3-5-7-10/h3-7,9,12H,8H2,1-2H3","InChIKey":"PCDVFYKROPOLBF-UHFFFAOYSA-N","MeSH Headers":[{"Id":"M0153493","Link":"https://id.nlm.nih.gov/mesh/M0153493.html","Name":"N-hydroxymethamphetamine","Ref":8},{"Id":"DescTree","Link":"https://www.nlm.nih.gov/mesh/meshhome.html","Name":"MeSH Tree","Ref":10},{"Id":"PubMed from MeSH","Link":"https://www.nlm.nih.gov/mesh/meshhome.html","Name":null,"Ref":15}],"MolecularFormula":"C\u003csub\u003e10\u003c/sub\u003eH\u003csub\u003e15\u003c/sub\u003eNO","MolecularWeight":"165.23 g/mol","PubChemId":6452608,"PubChemTitle":"N-Hydroxymethamphetamine","Reddit Experience Reports":[],"RefChem":"163542","RefCount":2,"RefCur":"","References":[{"Name":"Wikipedia","Urls":[{"Link":"https://en.wikipedia.org/wiki/N-Hydroxymethamphetamine","Name":"N-Hydroxymethamphetamine","Sub":false}]},{"Name":"Wikidata","Urls":[{"Link":"https://www.wikidata.org/wiki/Q82949063","Name":"N-Hydroxymethamphetamine","Sub":false}]},{"Name":"PubChem","Urls":[{"Link":"https://pubchem.ncbi.nlm.nih.gov/compound/6452608","Name":"N-Hydroxymethamphetamine","Sub":false}]},{"Name":"Common Chemistry","Urls":[{"Link":"https://commonchemistry.cas.org/detail?cas_rn=52271-36-0","Name":"N-Hydroxymethamphetamine","Sub":false}]},{"Name":"EPA DSSTox","Urls":[{"Link":"https://comptox.epa.gov/dashboard/chemical/details/DTXSID90966646","Name":"N-Hydroxymethamphetamine","Sub":false}]}],"Refs":["National Center for Biotechnology Information. PubChem Compound Summary for CID 6452608, N-Hydroxymethamphetamine. Accessed August 22, 2026. \u003ca href=https://pubchem.ncbi.nlm.nih.gov/compound/6452608\u003ehttps://pubchem.ncbi.nlm.nih.gov/compound/6452608\u003c/a\u003e"],"SMILES":"CC(CC1=CC=CC=C1)N(C)O","SaltData":[],"Salts":[],"Scheduling":[],"StereoisomerData":[{"ChemicalClasses":["amphetamine"],"SMILES":"C[C@H](CC1=CC=CC=C1)N(C)O","Structure":"\u003csvg xmlns=\"http://www.w3.org/2000/svg\" preserveAspectRatio=\"none\" style=\"display:block\" viewBox=\"0 0 81.407 49.988\"\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=\"#ff0d0d\" stroke=\"#000\" stroke-linecap=\"round\" stroke-linejoin=\"round\" stroke-width=\".8\"\u003e\u003cpath fill=\"#fff\" stroke=\"none\" d=\"M0 0h82v50H0z\"/\u003e\u003cg class=\"mol\"\u003e\u003cg class=\"bond\"\u003e\u003cpath d=\"M54.304 26.013h-.8M54.59 28.19h-1.372M54.876 30.367h-1.943M55.162 32.544h-2.515M55.447 34.721h-3.086M55.733 36.898h-3.658M56.019 39.075H51.79M56.305 41.253h-4.801\"/\u003e\u003c/g\u003e\u003cpath d=\"m53.904 26.013-13.198-7.62M40.706 18.393l-13.198 7.62\" class=\"bond\"/\u003e\u003cg class=\"bond\"\u003e\u003cpath d=\"m27.508 26.013-13.203-7.629M25.07 27.42 14.304 21.2\"/\u003e\u003c/g\u003e\u003cpath d=\"m14.305 18.384-13.199 7.62\" class=\"bond\"/\u003e\u003cg class=\"bond\"\u003e\u003cpath d=\"m1.106 26.004.005 15.249M3.545 27.412l.004 12.433\"/\u003e\u003c/g\u003e\u003cpath d=\"m1.111 41.253 13.203 7.628\" class=\"bond\"/\u003e\u003cg class=\"bond\"\u003e\u003cpath d=\"m14.314 48.881 13.199-7.62M14.315 46.065l10.759-6.212\"/\u003e\u003c/g\u003e\u003cpath d=\"m27.508 26.013.005 15.248M53.904 26.013l9.92-5.727M70.381 20.286l9.92 5.727M67.103 14.292V7.345\" class=\"bond\"/\u003e\u003cpath fill=\"#3050f8\" stroke=\"none\" d=\"M65.209 15.892h.911l2.215 4.185v-4.185h.661v5.001h-.911l-2.221-4.185v4.185h-.655z\" class=\"atom\"/\u003e\u003cg stroke=\"none\" class=\"atom\"\u003e\u003cpath d=\"M67.105 1.108q-.738 0-1.172.553-.429.548-.429 1.495 0 .946.429 1.494.434.547 1.172.547.739 0 1.167-.547.429-.548.429-1.494 0-.947-.429-1.495-.428-.553-1.167-.553m0-.548q1.054 0 1.679.708.631.703.631 1.888 0 1.178-.631 1.887-.625.702-1.679.702-1.053 0-1.684-.702-.631-.703-.631-1.887t.631-1.888Q66.052.56 67.105.56M69.987.649h.678v2.048h2.459V.649h.673V5.65h-.673V3.269h-2.459V5.65h-.678z\"/\u003e\u003c/g\u003e\u003cpath stroke=\"#3050f8\" d=\"m63.824 20.286-4.96 2.864M70.381 20.286l4.96 2.864M67.103 14.292v-3.473\" class=\"hi\"/\u003e\u003cpath stroke=\"#ff0d0d\" d=\"M67.103 7.345v3.474M67.103 7.345v3.474\" class=\"hi\"/\u003e\u003c/g\u003e\u003c/g\u003e\u003c/svg\u003e","Title":"(R)-N-Hydroxymethamphetamine"},{"ChemicalClasses":["amphetamine"],"SMILES":"C[C@@H](CC1=CC=CC=C1)N(C)O","Structure":"\u003csvg xmlns=\"http://www.w3.org/2000/svg\" preserveAspectRatio=\"none\" style=\"display:block\" viewBox=\"0 0 81.407 49.988\"\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=\"#ff0d0d\" stroke=\"#000\" stroke-linecap=\"round\" stroke-linejoin=\"round\" stroke-width=\".8\"\u003e\u003cpath fill=\"#fff\" stroke=\"none\" d=\"M0 0h82v50H0z\"/\u003e\u003cg class=\"mol\"\u003e\u003cpath fill=\"#000\" stroke=\"none\" d=\"M54.304 26.013h-.8l-2 15.24h4.801z\" class=\"bond\"/\u003e\u003cpath d=\"m53.904 26.013-13.198-7.62M40.706 18.393l-13.198 7.62\" class=\"bond\"/\u003e\u003cg class=\"bond\"\u003e\u003cpath d=\"m27.508 26.013-13.203-7.629M25.07 27.42 14.304 21.2\"/\u003e\u003c/g\u003e\u003cpath d=\"m14.305 18.384-13.199 7.62\" class=\"bond\"/\u003e\u003cg class=\"bond\"\u003e\u003cpath d=\"m1.106 26.004.005 15.249M3.545 27.412l.004 12.433\"/\u003e\u003c/g\u003e\u003cpath d=\"m1.111 41.253 13.203 7.628\" class=\"bond\"/\u003e\u003cg class=\"bond\"\u003e\u003cpath d=\"m14.314 48.881 13.199-7.62M14.315 46.065l10.759-6.212\"/\u003e\u003c/g\u003e\u003cpath d=\"m27.508 26.013.005 15.248M53.904 26.013l9.92-5.727M70.381 20.286l9.92 5.727M67.103 14.292V7.345\" class=\"bond\"/\u003e\u003cpath fill=\"#3050f8\" stroke=\"none\" d=\"M65.209 15.892h.911l2.215 4.185v-4.185h.661v5.001h-.911l-2.221-4.185v4.185h-.655z\" class=\"atom\"/\u003e\u003cg stroke=\"none\" class=\"atom\"\u003e\u003cpath d=\"M67.105 1.108q-.738 0-1.172.553-.429.548-.429 1.495 0 .946.429 1.494.434.547 1.172.547.739 0 1.167-.547.429-.548.429-1.494 0-.947-.429-1.495-.428-.553-1.167-.553m0-.548q1.054 0 1.679.708.631.703.631 1.888 0 1.178-.631 1.887-.625.702-1.679.702-1.053 0-1.684-.702-.631-.703-.631-1.887t.631-1.888Q66.052.56 67.105.56M69.987.649h.678v2.048h2.459V.649h.673V5.65h-.673V3.269h-2.459V5.65h-.678z\"/\u003e\u003c/g\u003e\u003cpath stroke=\"#3050f8\" d=\"m63.824 20.286-4.96 2.864M70.381 20.286l4.96 2.864M67.103 14.292v-3.473\" class=\"hi\"/\u003e\u003cpath stroke=\"#ff0d0d\" d=\"M67.103 7.345v3.474M67.103 7.345v3.474\" class=\"hi\"/\u003e\u003c/g\u003e\u003c/g\u003e\u003c/svg\u003e","Title":"(S)-N-Hydroxymethamphetamine"}],"StereoisomerType":"enantiomer","Stereoisomers":["(R)-N-Hydroxymethamphetamine","(S)-N-Hydroxymethamphetamine"],"Structure":"\u003csvg xmlns=\"http://www.w3.org/2000/svg\" preserveAspectRatio=\"none\" style=\"display:block\" viewBox=\"0 0 81.407 49.988\"\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=\"#ff0d0d\" stroke=\"#000\" stroke-linecap=\"round\" stroke-linejoin=\"round\" stroke-width=\".8\"\u003e\u003cpath fill=\"#fff\" stroke=\"none\" d=\"M0 0h82v50H0z\"/\u003e\u003cg class=\"mol\"\u003e\u003cpath d=\"M53.904 41.253v-15.24M53.904 26.013l-13.198-7.62M40.706 18.393l-13.198 7.62\" class=\"bond\"/\u003e\u003cg class=\"bond\"\u003e\u003cpath d=\"m27.508 26.013-13.203-7.629M25.07 27.42 14.304 21.2\"/\u003e\u003c/g\u003e\u003cpath d=\"m14.305 18.384-13.199 7.62\" class=\"bond\"/\u003e\u003cg class=\"bond\"\u003e\u003cpath d=\"m1.106 26.004.005 15.249M3.545 27.412l.004 12.433\"/\u003e\u003c/g\u003e\u003cpath d=\"m1.111 41.253 13.203 7.628\" class=\"bond\"/\u003e\u003cg class=\"bond\"\u003e\u003cpath d=\"m14.314 48.881 13.199-7.62M14.315 46.065l10.759-6.212\"/\u003e\u003c/g\u003e\u003cpath d=\"m27.508 26.013.005 15.248M53.904 26.013l9.92-5.727M70.381 20.286l9.92 5.727M67.103 14.292V7.345\" class=\"bond\"/\u003e\u003cpath fill=\"#3050f8\" stroke=\"none\" d=\"M65.209 15.892h.911l2.215 4.185v-4.185h.661v5.001h-.911l-2.221-4.185v4.185h-.655z\" class=\"atom\"/\u003e\u003cg stroke=\"none\" class=\"atom\"\u003e\u003cpath d=\"M67.105 1.108q-.738 0-1.172.553-.429.548-.429 1.495 0 .946.429 1.494.434.547 1.172.547.739 0 1.167-.547.429-.548.429-1.494 0-.947-.429-1.495-.428-.553-1.167-.553m0-.548q1.054 0 1.679.708.631.703.631 1.888 0 1.178-.631 1.887-.625.702-1.679.702-1.053 0-1.684-.702-.631-.703-.631-1.887t.631-1.888Q66.052.56 67.105.56M69.987.649h.678v2.048h2.459V.649h.673V5.65h-.673V3.269h-2.459V5.65h-.678z\"/\u003e\u003c/g\u003e\u003cpath stroke=\"#3050f8\" d=\"m63.824 20.286-4.96 2.864M70.381 20.286l4.96 2.864M67.103 14.292v-3.473\" class=\"hi\"/\u003e\u003cpath stroke=\"#ff0d0d\" d=\"M67.103 7.345v3.474M67.103 7.345v3.474\" class=\"hi\"/\u003e\u003c/g\u003e\u003c/g\u003e\u003c/svg\u003e","Subjective Effects":{"Cognitive Effects":["Analysis enhancement","Ego inflation","Focus enhancement","Increased music appreciation","Motivation enhancement","Thought acceleration","Wakefulness","Disinhibition","Suggestibility suppression","Cognitive euphoria","Compulsive redosing","Mania"],"Physical Effects":["Increased libido","Stamina enhancement","Stimulation","Appetite suppression","Dehydration","Dry mouth","Restless legs","Shakiness","Teeth grinding","Abnormal heartbeat","Increased blood pressure","Increased heart rate","Vasoconstriction"],"Visual Effects":[]},"Title":"N-Hydroxymethamphetamine","Wikidata":"Q82949063","Wikipedia":"N-Hydroxymethamphetamine","XLogP":2.2}