{"Abbreviation":"4-MA","Aliases":["Aptrol","p-Methylamphetamine","p-Methylamfetamine","P-TAP","PAL-313","-α,4-Dimethylbenzeneethanamine","Benzeneethanamine, α,4-dimethyl-, (+-)-","1-p-Tolyl-2-propylamine","4-12-00-02834","p-.α.-Dimethylphenethylamine"],"CAS":"64-11-9","ChEMBL":"CHEMBL166183","ChemicalClasses":["amphetamine"],"Chirality":"racemic","Classes":["Stimulant"],"DrugClasses":[],"EliminationHalfLife":"6–12 hours","Erowid Experience Reports":[{"Id":"114344","Title":"Massive Visuals and Satori"}],"FullSalts":["4-Methylamphetamine hemisulfate"],"HMDB ID":"HMDB0246503","HeavyAtomCount":11,"IUPACName":"1-(4-methylphenyl)propan-2-amine","InChI":"InChI=1S/C10H15N/c1-8-3-5-10(6-4-8)7-9(2)11/h3-6,9H,7,11H2,1-2H3","InChIKey":"ZDHZDWSHLNBTEB-UHFFFAOYSA-N","MolecularFormula":"C\u003csub\u003e10\u003c/sub\u003eH\u003csub\u003e15\u003c/sub\u003eN","MolecularWeight":"149.23 g/mol","Opticalactivity":"( + / - )","PD":"PD057774","PrevSalts":["hemisulfate"],"PubChemId":199116,"Record Description":["4-Methylamphetamine has been reported in Thymus quinquecostatus with data available.","4-Methylamphetamine (4-MA; PAL-313; Aptrol; p-TAP) is a stimulant and anorectic drug of the phenethylamine and amphetamine chemical classes.In vitro, it acts as a potent and balanced serotonin, norepinephrine, and dopamine releasing agent with Ki affinity values of 53.4nM, 22.2nM, and 44.1nM at the serotonin, norepinephrine, and dopamine transporters, respectively.","Wikipedia|List of designer drugs|Empathogens|Amphetamines"],"RefCount":3,"References":[{"Name":"Wikipedia","Urls":[{"Link":"https://en.wikipedia.org/wiki/4-Methylamphetamine","Name":"4-Methylamphetamine","Sub":false}]},{"Name":"Wikidata","Urls":[{"Link":"https://www.wikidata.org/wiki/Q685310","Name":"4-Methylamphetamine","Sub":false},{"Link":"https://www.wikidata.org/wiki/Q27253458","Name":"(+)-4-Methylamphetamine","Sub":true},{"Link":"https://www.wikidata.org/wiki/Q27281304","Name":"(-)-4-Methylamphetamine","Sub":true}]},{"Name":"PubChem","Urls":[{"Link":"https://pubchem.ncbi.nlm.nih.gov/compound/199116","Name":"4-Methylamphetamine","Sub":false},{"Link":"https://pubchem.ncbi.nlm.nih.gov/compound/36689297","Name":"(+)-4-Methylamphetamine","Sub":true},{"Link":"https://pubchem.ncbi.nlm.nih.gov/compound/18602795","Name":"(-)-4-Methylamphetamine","Sub":true}]},{"Name":"ChEMBL","Urls":[{"Link":"https://www.ebi.ac.uk/chembl/explore/compound/CHEMBL166183","Name":"4-Methylamphetamine","Sub":false}]},{"Name":"Probes \u0026 Drugs","Urls":[{"Link":"https://www.probes-drugs.org/compound/PD057774","Name":"4-Methylamphetamine","Sub":false}]},{"Name":"Common Chemistry","Urls":[{"Link":"https://commonchemistry.cas.org/detail?cas_rn=64-11-9","Name":"4-Methylamphetamine","Sub":false},{"Link":"https://commonchemistry.cas.org/detail?cas_rn=81601-14-1","Name":"(+)-4-Methylamphetamine","Sub":true},{"Link":"https://commonchemistry.cas.org/detail?cas_rn=788775-45-1","Name":"(-)-4-Methylamphetamine","Sub":true}]},{"Name":"HMDB","Urls":[{"Link":"https://hmdb.ca/metabolites/HMDB0246503","Name":"4-Methylamphetamine","Sub":false}]},{"Name":"UNII","Urls":[{"Link":"https://gsrs.ncats.nih.gov/ginas/app/ui/substances/9E273KL7HS","Name":"4-Methylamphetamine","Sub":false},{"Link":"https://gsrs.ncats.nih.gov/ginas/app/ui/substances/20FWH19YGI","Name":"(+)-4-Methylamphetamine","Sub":true},{"Link":"https://gsrs.ncats.nih.gov/ginas/app/ui/substances/J7DV880HGB","Name":"(-)-4-Methylamphetamine","Sub":true}]},{"Name":"EPA DSSTox","Urls":[{"Link":"https://comptox.epa.gov/dashboard/chemical/details/DTXSID50945351","Name":"4-Methylamphetamine","Sub":false}]}],"Refs":["National Center for Biotechnology Information. PubChem Compound Summary for CID 199116, 4-Methylamphetamine. Accessed June 25, 2025. \u003ca href=https://pubchem.ncbi.nlm.nih.gov/compound/199116\u003ehttps://pubchem.ncbi.nlm.nih.gov/compound/199116\u003c/a\u003e","U.S. Food and Drug Administration; National Center for Advancing Translational Sciences. 4-Methylamphetamine. UNII: 9E273KL7HS. Global Substance Registration System. Accessed June 25, 2025. \u003ca href=https://gsrs.ncats.nih.gov/ginas/app/beta/substances/9E273KL7HS\u003ehttps://gsrs.ncats.nih.gov/ginas/app/beta/substances/9E273KL7HS\u003c/a\u003e"],"SMILES":"CC1=CC=C(C=C1)CC(C)N","Salts":["hemisulfate"],"SaltsAcidCount":[0],"SaltsAmineCount":[2],"SaltsUNII":["04XMA0R4NF"],"Scheduling":[{"gov":"Canada","ref":[],"schedule":"Schedule I substance"},{"gov":"United Kingdom","ref":[],"schedule":"Class A substance"},{"gov":"Germany","ref":[],"schedule":"Anlage II substance"},{"gov":"United States","ref":[],"schedule":"List of Schedule II drugs (US)|Schedule II (isomer of Methamphetamine) substance"}],"StereoisomerRacemic":"(RS)-4-Methylamphetamine","Stereoisomers":["(+)-4-Methylamphetamine","(-)-4-Methylamphetamine"],"StereoisomersUNII":["20FWH19YGI","J7DV880HGB"],"StoreUNII":["9E273KL7HS"],"StructureBase64":"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","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"],"Sensory Effects":[]},"Title":"4-Methylamphetamine","UNII":"9E273KL7HS","Wikidata":"Q685310","Wikipedia":"4-Methylamphetamine","XLogP":2.1}