{"ATC Code":"R - Respiratory system","Abbreviation":"PPA","Aliases":["Propadrine","Rhindecon","Mucron","Super Odrinex","Phenylpropanolamina","Phenylpropanolaminum","Phenylfenesin","Rinexin","Fansia","Fenilpropanolamina"],"Biological Half-Life":"2.1 to 3.4 hours.","CAS":"14838-15-4","ChEBI":"CHEBI:80680","ChEMBL":"CHEMBL136560","ChemicalClasses":["phenylethanolamine"],"Chirality":"racemic","Classes":["Sympathomimetic"],"Color/Form":"White, crystalline powder","Decomposition":"When heated to decomposition it emits very toxic fumes of nitroxides.","Dosing Info":[],"Drug Indication":"For the treatment of nasal congestion, control of urinary incontinence, priapism and obesity.","Drug Warnings":"The Food and Drug Administration (FDA) is issuing a public health advisory concerning phenylpropanolamine hydrochloride. This drug is widely used as a nasal decongestant (in over-the-counter and prescription drug products) and for weight control (in over-the-counter drug products). FDA is taking steps to remove phenylpropanolamine from all drug products and has requested that all drug companies discontinue marketing products containing phenylpropanolamine.  Phenylpropanolamine has been marketed for many years. A recent study reported that taking phenylpropanolamine increases the risk of hemorrhagic stroke (bleeding into the brain or into tissue surrounding the brain) in women. Men may also be at risk. Although the risk of hemorrhagic stroke is very low, FDA recommends that consumers not use any products that contain phenylpropanolamine.","DrugClasses":["depressant"],"DurationOfAction":"Oral: 3\u0026nbsphours","EINECS":"211-850-9","EliminationHalfLife":"4 (3.7–4.9)\u0026nbsphours","European Community (EC) Number":"207-755-7","FullSalts":["Phenylpropanolamine hydrochloride","Phenylpropanolamine maleate","Phenylpropanolamine bitartrate","Phenylpropanolamine sulfate"],"HeavyAtomCount":11,"IUPACName":"(1R,2S)-2-amino-1-phenylpropan-1-ol","InChI":"InChI=1S/C9H13NO/c1-7(10)9(11)8-5-3-2-4-6-8/h2-7,9,11H,10H2,1H3/t7-,9-/m0/s1","InChIKey":"DLNKOYKMWOXYQA-CBAPKCEASA-N","MeSH Pharmacological Classification":"Agents that are used to suppress appetite. (See all compounds classified as Appetite Depressants.)","Melting Point":"190-194 °C","MolecularFormula":"C\u003csub\u003e9\u003c/sub\u003eH\u003csub\u003e13\u003c/sub\u003eNO","MolecularWeight":"151.21 g/mol","Odor":"Slight aromatic odor","Opticalactivity":"( + / - )","Pharmacodynamics":"Phenylpropanolamine (PPA), a sympathomimetic agent structurally similar to pseudoephedrine, is used to treat nasal congestion. Phenylpropanolamine is found in appetite suppressant formulations and with guaifenesinin in cough-cold formulations. In 2000, the FDA requested that all drug companies discontinue marketing products containing phenylpropanolamine, due to an increased risk of hemorrhagic stroke in women who used phenylpropanolamine.","PrevSalts":["hydrochloride","maleate","bitartrate","sulfate"],"PubChemId":10297,"Record Description":["(-)-norephedrine is an amphetamine that is propylbenzene substituted by a hydroxy group at position 1 and by an amino group at position 2 (the 1R,2S-stereoisomer). It is a plant alkaloid. It has a role as a plant metabolite. It is a member of amphetamines and a phenethylamine alkaloid.","Phenylpropanolamine is a sympathomimetic agent that acts as a nonselective adrenergic receptor agonist and norepinephrine reuptake inhibitor. It has been used as a decongestant and appetite suppressant. Currently, it is withdrawn from the market in Canada and the United States due to the risk for hemorrahgic strokes.","(-)-Norephedrine has been reported in Catha edulis, Ephedra sinica, and Thymus quinquecostatus with data available.","Phenylpropanolamine is an alpha- and beta-adrenergic receptor agonist with sympathomimetic activity. Phenylpropanolamine (PPA) binds to and activates alpha- and beta-adrenergic receptors in the mucosa of the respiratory tract resulting in vasoconstriction and reduction in swelling of nasal mucous membranes and reduction in tissue hyperemia, edema, and nasal congestion. This agent also stimulates the release of norepinephrine from its storage sites resulting in the effects already described. Finally, PPA indirectly stimulates beta-receptors producing tachycardia and a positive inotropic effect.","A sympathomimetic that acts mainly by causing release of NOREPINEPHRINE but also has direct agonist activity at some adrenergic receptors. It is most commonly used as a nasal vasoconstrictor and an appetite depressant.","See also: Phenylpropanolamine Hydrochloride (has salt form).","(-)-norephedrine is an amphetamine that is propylbenzene substituted by a hydroxy group at position 1 and by an amino group at position 2 (the 1R,2S-stereoisomer). It is a plant alkaloid. It has a role as a plant metabolite. It is a member of amphetamines and a phenethylamine alkaloid."],"References":[{"Name":"Wikipedia","Urls":[{"Link":"https://en.wikipedia.org/wiki/Phenylpropanolamine","Name":"Phenylpropanolamine","Sub":false}]},{"Name":"Wikidata","Urls":[{"Link":"https://www.wikidata.org/wiki/Q26840801","Name":"Phenylpropanolamine","Sub":false},{"Link":"https://www.wikidata.org/wiki/Q413147","Name":"(+)-Phenylpropanolamine","Sub":true}]},{"Name":"DrugBank","Urls":[{"Link":"https://go.drugbank.com/drugs/DB00397","Name":"Phenylpropanolamine","Sub":false}]},{"Name":"PubChem","Urls":[{"Link":"https://pubchem.ncbi.nlm.nih.gov/compound/10297","Name":"Phenylpropanolamine","Sub":false},{"Link":"https://pubchem.ncbi.nlm.nih.gov/compound/26934","Name":"(+)-Phenylpropanolamine","Sub":true}]},{"Name":"ChEMBL","Urls":[{"Link":"https://www.ebi.ac.uk/chembl/explore/compound/CHEMBL136560","Name":"Phenylpropanolamine","Sub":false},{"Link":"https://www.ebi.ac.uk/chembl/explore/compound/CHEMBL2092846","Name":"(+)-Phenylpropanolamine","Sub":true}]},{"Name":"ChEBI","Urls":[{"Link":"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:80680","Name":"Phenylpropanolamine","Sub":false},{"Link":"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:36","Name":"(+)-Phenylpropanolamine","Sub":true}]},{"Name":"Common Chemistry","Urls":[{"Link":"https://commonchemistry.cas.org/detail?cas_rn=14838-15-4","Name":"Phenylpropanolamine","Sub":false}]},{"Name":"KEGG","Urls":[{"Link":"https://www.kegg.jp/entry/C07911","Name":"Phenylpropanolamine","Sub":false},{"Link":"https://www.kegg.jp/entry/C02343","Name":"(+)-Phenylpropanolamine","Sub":true}]},{"Name":"UNII","Urls":[{"Link":"https://gsrs.ncats.nih.gov/ginas/app/ui/substances/33RU150WUN","Name":"Phenylpropanolamine","Sub":false},{"Link":"https://gsrs.ncats.nih.gov/ginas/app/ui/substances/7875H6443P","Name":"(+)-Phenylpropanolamine","Sub":true}]},{"Name":"EPA DSSTox","Urls":[{"Link":"https://comptox.epa.gov/dashboard/chemical/details/DTXSID4023466","Name":"Phenylpropanolamine","Sub":false},{"Link":"https://comptox.epa.gov/dashboard/chemical/details/DTXSID301313960","Name":"(+)-Phenylpropanolamine","Sub":true}]}],"Reported Fatal Dose":"/In adults:/ toxic dose /is 100 mg/ (although CNS and cardiovascular hyperadrenergic signs such as sweating and skin flushing may occur at a lower dose).","SMILES":"C[C@@H]([C@@H](C1=CC=CC=C1)O)N","Salts":["hydrochloride","maleate","bitartrate","sulfate"],"SaltsAcidCount":[1,1,0,1],"SaltsAmineCount":[1,1,1,2],"SaltsUNII":["8D5I63UE1Q","86ILV507ZN","B48FTC099P","TQA3O9M79V"],"Scheduling":[{"gov":"Australia","schedule":"S4 substance"},{"gov":"Brazil","schedule":"F3 substance"},{"gov":"Canada","schedule":"Schedule VI substance"}],"Solubility":"Freely soluble","StereoisomerRacemic":"(RS)-Phenylpropanolamine","Stereoisomers":["(+)-Phenylpropanolamine","(-)-Phenylpropanolamine","(-)-Phenylpropanolamine"],"StereoisomersUNII":["7875H6443P","",""],"StoreUNII":["33RU150WUN"],"StructureBase64":"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Uses":"Adrenergic alpha-Agonists; Adrenergic Agents; Appetite Depressants; Nasal Decongestants; Sympathomimetics","Title":"Phenylpropanolamine","UNII":"33RU150WUN","Wikidata":"Q26840801","Wikipedia":"Phenylpropanolamine","XLogP":0.8}