{"Absorption, Distribution and Excretion":"Readily absorbed from the gastro-intestinal tract and buccal mucosa.","Aliases":["3-Methyl-2-phenylmorpholine","Oxazimedrine","Phenmetrazin","2-Phenyl-3-methylmorpholine","Psychamine A 66","Probese-P","Fenmetrazin","Fenmetrazina","Defenmetrazin","Phenmetrazinum","Morpholine, 3-methyl-2-phenyl-","3-Methyl-2-phenyltetrahydro-2H-1,4-oxazine","2-Phenyl-3-methyltetrahydro-1,4-oxazine","CHEBI:8067","Phenmetraline","Dtxcid603455","205-143-4","XA501VL3VR","Dexphenmetrazine","DEA No. 1631","2-Fenyl-3-methylmorfolin","HSDB 3156","Ncgc00164535-01","Ncgc00164535-02","Einecs 205-143-4","Brn 0140490","S-trans-Phenmetrazine","Schembl33984","Schembl7963497","Chembl1201208","HCA91912","SBB072145","Akos003662804","AB07481","DB00830","57919-12-7","AC-16023","ST081100","NS00002554","C07432"],"Biological Half-Life":"16 to 31 hours","Boiling Point":"138-140 °C @ 12 mm Hg","CAS":"134-49-6","ChemicalClasses":["2-phenylmorpholine"],"Chirality":"racemic","Color/Form":"Liquid","DTXSID":"5023455","Decomposition":"When heated to decomposition it emits toxic fumes of nitroxides.","Drug Indication":"Used as an anorectic in the treatment of obesity.","Drug Warnings":"As with other anorexigenic agents, prolonged admin of phenmetrazine is not indicated. ... Habituation has been reported with phenmetrazine; discontinuance of the drug, however, does not result in serious withdrawal symptoms although some patients may experience depression \u0026 fatigue. /Phenmetrazine hydrochloride/","DurationOfAction":"","EliminationHalfLife":"16 – 31 hours","Erowid Experience Reports":[],"Esters":[],"European Community (EC) Number":"205-143-4","Formating":[],"HMDB ID":"HMDB0014968","Health Effects":"Using large amounts of these drugs can result in a condition known as amphetamine psychosis -- which can result in auditory, visual and tactile hallucinations, intense paranoia, irrational thoughts and beliefs, delusions, and mental confusion.","HeavyAtomCount":13,"Human Drugs":"Pharmaceuticals","IUPACName":"3-methyl-2-phenylmorpholine","InChI":"InChI=1S/C11H15NO/c1-9-11(13-8-7-12-9)10-5-3-2-4-6-10/h2-6,9,11-12H,7-8H2,1H3","InChIKey":"OOBHFESNSZDWIU-UHFFFAOYSA-N","Interactions":"A double blind controlled study in psychiatric patients indicated that chlorpromazine reduced the ability of phenmetrazine to produce a weight loss /mechanism not established/. Another study in 30 obese psychiatric patients yielded similar results. Thus, it does appear that chlorpromazine (and possibly other phenothiazines) can reduce the efficacy of phenmetrazine, such as it is.","MeSH Headers":[{"Id":"M0016512","Link":"https://id.nlm.nih.gov/mesh/M0016512.html","Name":"Phenmetrazine","Ref":44},{"Id":"DescTree","Link":"https://www.nlm.nih.gov/mesh/meshhome.html","Name":"MeSH Tree","Ref":46},{"Id":"PubMed from MeSH","Link":"https://www.nlm.nih.gov/mesh/meshhome.html","Name":null,"Ref":61},{"Id":"M0001063","Link":"https://id.nlm.nih.gov/mesh/M0001063.html","Name":"Central Nervous System Stimulants","Ref":62},{"Id":"M0001614","Link":"https://id.nlm.nih.gov/mesh/M0001614.html","Name":"Appetite Depressants","Ref":63},{"Id":"M0020947","Link":"https://id.nlm.nih.gov/mesh/M0020947.html","Name":"Sympathomimetics","Ref":64}],"MeSH Pharmacological Classification":[{"Id":"M0001063","Link":"https://id.nlm.nih.gov/mesh/M0001063.html","Name":"Central Nervous System Stimulant","Ref":62},{"Id":"M0001614","Link":"https://id.nlm.nih.gov/mesh/M0001614.html","Name":"Appetite Depressant","Ref":63},{"Id":"M0020947","Link":"https://id.nlm.nih.gov/mesh/M0020947.html","Name":"Sympathomimetic","Ref":64}],"Mechanism of Action":"Phenmetrazine is thought to block the reuptake of norepinephrine and dopamine into the presynaptic neuron leading to an increase in the release of these monoamines into the extraneuronal space. Dopamine integrates incoming sensory stimuli, initiates and controls fine movement (nigro-neostriatal pathway), controls emotional behavior (midbrain mesolimbic-forebrain system) and controls hypothalamic-pituitary endocrine system (tubero-infundibular system). It is this latter effect on the tubero-infundibular systm that seems to lead to reduced food intake. Phenmetrazine also acts as a monoamine oxidase inhibitor.","Melting Point":"139 °C","Metabolism/Metabolites":"Primarily hepatic (via CYP3A and CYP2D6). Resistant to metabolism by monoamine oxidase. Metabolism involves deamination to para-hydroxyamphetamine and phenylacetone; this latter compound is subsequently oxidize to benzoic acid and excreted as glucuronide or glycine (hippuric acid) conjugate. Smaller amounts of amphetamine are converted to norephedrine by oxidation.","MolecularFormula":"C\u003csub\u003e11\u003c/sub\u003eH\u003csub\u003e15\u003c/sub\u003eNO","MolecularWeight":"177.24 g/mol","Non-Human Toxicity Values":"LD50 Rat oral 370 mg/kg","Pharmacodynamics":"Phenmetrazine is a sympathomimetic drug used primarily as an appetite depressant. Its actions and mechanisms are similar to dextroamphetamine. Amphetamines are non-catecholamine sympathomimetic amines with CNS stimulant activity. Phenmetrazine was originally sold under the tradename Preludin as an anorectic. It has since been removed from the market. It is by some considered to have a greater potential for addiction than the amphetamines, and has been abused in many countries, for example Sweden.","Physical Description":"Solid","PubChemId":4762,"PubChemTitle":"Phenmetrazine","Reagents":[],"RefChem":"860606","RefCount":3,"RefCur":"","References":[{"Name":"Wikipedia","Urls":[{"Link":"https://en.wikipedia.org/wiki/Phenmetrazine","Name":"Phenmetrazine","Sub":false}]},{"Name":"Wikidata","Urls":[{"Link":"https://www.wikidata.org/wiki/Q3329406","Name":"Phenmetrazine","Sub":false}]},{"Name":"DrugBank","Urls":[{"Link":"https://go.drugbank.com/DB00830","Name":"Phenmetrazine","Sub":false}]},{"Name":"PubChem","Urls":[{"Link":"https://pubchem.ncbi.nlm.nih.gov/compound/4762","Name":"Phenmetrazine","Sub":false}]},{"Name":"Common Chemistry","Urls":[{"Link":"https://commonchemistry.cas.org/detail?cas_rn=134-49-6","Name":"Phenmetrazine","Sub":false}]},{"Name":"HMDB","Urls":[{"Link":"https://hmdb.ca/metabolites/HMDB0014968","Name":"Phenmetrazine","Sub":false}]},{"Name":"KEGG","Urls":[{"Link":"https://www.kegg.jp/entry/C07432","Name":"Phenmetrazine","Sub":false}]},{"Name":"EPA DSSTox","Urls":[{"Link":"https://comptox.epa.gov/dashboard/chemical/details/DTXSID5023455","Name":"Phenmetrazine","Sub":false}]}],"Refs":["National Center for Biotechnology Information. PubChem Compound Summary for CID 4762, Phenmetrazine. Accessed May 18, 2026. \u003ca href=https://pubchem.ncbi.nlm.nih.gov/compound/4762\u003ehttps://pubchem.ncbi.nlm.nih.gov/compound/4762\u003c/a\u003e","Anvisa. RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial. Diário Oficial da União. March 31, 2023. Accessed May 18, 2026. \u003ca href=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992\u003ehttps://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992\u003c/a\u003e"],"SMILES":"CC1C(OCCN1)C2=CC=CC=C2","SaltData":[],"Salts":[],"Scheduling":[{"gov":"Australia","ref":[],"schedule":"S8 substance"},{"gov":"Brazil","ref":["2"],"schedule":"A3 substance"},{"gov":"Canada","ref":[],"schedule":"Schedule IV substance"},{"gov":"Germany","ref":[],"schedule":"Anlage II substance"},{"gov":"United Kingdom","ref":[],"schedule":"Class B substance"},{"act":"Controlled Substances Act (CSA)","gov":"United States","ref":[],"schedule":"Schedule I"},{"act":"Convention on Psychotropic Substances 1971","gov":"United Nations","ref":[],"schedule":"Schedule II drug"}],"Solubility":"\u003e5 mg/L","StereoisomerData":[{"SMILES":"C[C@H]1NCCO[C@@H]1C1=CC=CC=C1","Structure":"\u003csvg xmlns=\"http://www.w3.org/2000/svg\" preserveAspectRatio=\"none\" 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26.344h-.62v-2.286h-2.512v2.286h-.613v-4.9h.613v2.072h2.512v-2.072h.62z\"/\u003e\u003c/g\u003e\u003cpath stroke=\"#ff0d0d\" d=\"m40.621 12.584-.002 5.659M43.9 6.769l4.959-2.865\" class=\"hi\"/\u003e\u003cpath stroke=\"#3050f8\" d=\"m67.005 20.044.002-5.695M63.851 25.716l-5.022 2.901\" class=\"hi\"/\u003e\u003c/g\u003e\u003c/g\u003e\u003c/svg\u003e","Therapeutic Uses":"Adrenergic Agents; Adrenergic Uptake Inhibitors; Appetite Depressants; Central Nervous System Stimulants; Dopamine Agents; Dopamine Uptake Inhibitors; Sympathomimetics","Title":"Phenmetrazine","Toxicity Data":"Adult monkeys have an LD\u003csub\u003e50\u003c/sub\u003e of 15 to 20 mg/kg, whereas for young monkeys the LD\u003csub\u003e50\u003c/sub\u003e is only 5 mg/kg. (A308)","Wikidata":"Q3329406","Wikipedia":"Phenmetrazine","XLogP":1.4}