{"ATC Code":"R - Respiratory system","Abbreviation":"","Aliases":["(-)-NORPSEUDOEPHEDRINE","Norpseudoephedrine","37577-07-4","l-Pseudonorephedrine","NORPSEUDOEPHEDRINE, (-)-","QQ0FVC4PXS","(R,R)-(-)-Norpseudoephedrine","l-Nor-psi-ephedrine","NORPSEUDOEPHEDRINE, L-","(-)-threo-2-Amino-2-methyl-1-phenylethanol"],"Biological Half-Life":"2.1 to 3.4 hours.","CAS":"14838-15-4","ChEBI":"CHEBI:8104","ChEMBL":"CHEMBL1788114","Chirality":"absolute","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"],"European Community (EC) Number":"238-900-2","IUPACName":"(1R,2R)-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+/m1/s1","InChIKey":"DLNKOYKMWOXYQA-APPZFPTMSA-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":"UNSPECIFIED","PD":"PD017909","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.","PubChemId":162265,"Record Description":["Phenylpropanolamine is an amphetamine in which the parent 1-phenylpropan-2-amine skeleton is substituted at position 1 with an hydroxy group. A decongestant and appetite suppressant, it is commonly used in prescription and over-the-counter cough and cold preparations. It has a role as a sympathomimetic agent and a nasal decongestant.","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.","Norpseudoephedrine has been reported in Catha edulis and Ephedra sinica 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.","Phenylpropanolamine is an amphetamine in which the parent 1-phenylpropan-2-amine skeleton is substituted at position 1 with an hydroxy group. A decongestant and appetite suppressant, it is commonly used in prescription and over-the-counter cough and cold preparations. It has a role as a sympathomimetic agent and a nasal decongestant.","L-Norpseudoephedrine, or (−)-norpseudoephedrine, is a psychostimulant drug of the amphetamine family. It is one of the four optical isomers of phenylpropanolamine, the other three being cathine ((+)-norpseudoephedrine), (−)-norephedrine, and (+)-norephedrine; as well as one of the two enantiomers of norpseudoephedrine (the other, of course, being cathine).[1] Similarly to cathine, L-norpseudoephedrine acts as a releasing agent of norepinephrine (EC50 = 30 nM) and to a lesser extent of dopamine (EC50 = 294 nM).[2] Due to the 10-fold difference in its potency for inducing the release of the two neurotransmitters however, L-norpseudoephedrine could be called a modestly selective or preferential norepinephrine releasing agent, similarly to related compounds like ephedrine and pseudoephedrine."],"References":[{"name":"Wikipedia","url":"https://en.wikipedia.org/wiki/L-Norpseudoephedrine"},{"name":"Wikidata","url":"https://www.wikidata.org/wiki/Q6456100"},{"name":"DrugBank","url":"https://go.drugbank.com/drugs/DB00397"},{"name":"PubChem","url":"https://pubchem.ncbi.nlm.nih.gov/compound/162265"},{"name":"ChemSpider","url":"https://www.chemspider.com/Chemical-Structure.142493.html"},{"name":"ChEMBL","url":"https://www.ebi.ac.uk/chembl/explore/compound/CHEMBL1788114"},{"name":"ChEBI","url":"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:8104"},{"name":"Probes \u0026 Drugs","url":"https://www.probes-drugs.org/compound/PD017909"},{"name":"Common Chemistry","url":"https://commonchemistry.cas.org/detail?cas_rn=14838-15-4"},{"name":"KEGG","url":"https://www.kegg.jp/entry/C07911"},{"name":"UNII","url":"https://gsrs.ncats.nih.gov/ginas/app/ui/substances/QQ0FVC4PXS"},{"name":"EPA DSSTox","url":"https://comptox.epa.gov/dashboard/chemical/details/DTXSID001045718"}],"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","Solubility":"Freely soluble","StructureBase64":"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Uses":"Adrenergic alpha-Agonists; Adrenergic Agents; Appetite Depressants; Nasal Decongestants; Sympathomimetics","Title":"L-Norpseudoephedrine","UNII":"QQ0FVC4PXS","Wikidata":"Q6456100","XLogP":0.8}