{"ATC Code":"C - Cardiovascular system","Abbreviation":"Metaradrine","Aliases":["Hydroxynorephedrine","m-Hydroxypropadrine","Pressonex","m-Hydroxy norephedrine","1-Metaraminol","(-)-Erythro-metaraminol","Pressorol","m-Hydroxyphenylpropanolamine","Icoral B","Metaraminolum"],"CAS":"54-49-9","ChEBI":"CHEBI:6794","ChEMBL":"CHEMBL1201319","ChemicalClasses":["phenylethanolamine"],"Chirality":"absolute","Classes":["Sympathomimetic"],"Decomposition":"When heated to decomposition it emits toxic fumes of nitroxides.","Dosing Info":[],"Drug Indication":"For the treatment and prevention of hypotension due to hemorrhage, spinal anesthesia, and shock associated with brain damage","Drug Warnings":"VET: CONTINUED USE MAY DEPLETE NOREPINEPHRINE STORES.","DrugClasses":[],"EliminationHalfLife":"","FullSalts":["Metaraminol bitartrate"],"HMDB ID":"HMDB0014748","HeavyAtomCount":12,"Human Drugs":"Pharmaceuticals","IUPACName":"3-[(1R,2S)-2-amino-1-hydroxypropyl]phenol","InChI":"InChI=1S/C9H13NO2/c1-6(10)9(12)7-3-2-4-8(11)5-7/h2-6,9,11-12H,10H2,1H3/t6-,9-/m0/s1","InChIKey":"WXFIGDLSSYIKKV-RCOVLWMOSA-N","MeSH Pharmacological Classification":"Drugs that mimic the effects of stimulating postganglionic adrenergic sympathetic nerves. Included here are drugs that directly stimulate adrenergic receptors and drugs that act indirectly by provoking the release of adrenergic transmitters. (See all compounds classified as Sympathomimetics.)","Melting Point":"107.5 °C","MolecularFormula":"C\u003csub\u003e9\u003c/sub\u003eH\u003csub\u003e13\u003c/sub\u003eNO\u003csub\u003e2\u003c/sub\u003e","MolecularWeight":"167.20 g/mol","Opticalactivity":"UNSPECIFIED","Pharmacodynamics":"Metaraminol is a potent sympathomimetic amine that increases both systolic and diastolic blood pressure. Metaraminol is indicated for prevention and treatment of the acute hypotensive state occurring with spinal anesthesia. It is also indicated as adjunctive treatment of hypotension due to hemorrhage, reactions to medications, surgical complications, and shock associated with brain damage due to trauma or tumor. Metaraminol acts on both \u0026alpha;1-adrenergic receptors but appears to have no effect on \u0026beta;-adrenergic receptors. It acts by increasing the force of the heart's pumping action as well as constricting peripheral blood vessels.","Physical Description":"Solid","PrevSalts":["bitartrate"],"PubChemId":5906,"Record Description":["Metaraminol is a member of the class of phenylethanolamines that is 2-amino-1-phenylethanol substituted by a methyl group at position 2 and a phenolic hydroxy group at position 1. A sympathomimetic agent , it is used in the treatment of hypotension. It has a role as an alpha-adrenergic agonist, a sympathomimetic agent and a vasoconstrictor agent.","An adrenergic agonist that acts predominantly at alpha adrenergic receptors and also stimulates the release of norepinephrine. It has been used primarily as a vasoconstrictor in the treatment of hypotension.","METARAMINOL is a small molecule drug with a maximum clinical trial phase of IV (across all indications) that was first approved in 1954 and is indicated for cardiovascular disease and has 2 investigational indications.","A sympathomimetic agent that acts predominantly at alpha-1 adrenergic receptors. It has been used primarily as a vasoconstrictor in the treatment of HYPOTENSION.","Metaraminol is a member of the class of phenylethanolamines that is 2-amino-1-phenylethanol substituted by a methyl group at position 2 and a phenolic hydroxy group at position 1. A sympathomimetic agent , it is used in the treatment of hypotension. It has a role as an alpha-adrenergic agonist, a sympathomimetic agent and a vasoconstrictor agent."],"References":[{"Name":"Wikipedia","Urls":[{"Link":"https://en.wikipedia.org/wiki/Metaraminol","Name":"Metaraminol","Sub":false}]},{"Name":"Wikidata","Urls":[{"Link":"https://www.wikidata.org/wiki/Q409981","Name":"Metaraminol","Sub":false}]},{"Name":"DrugBank","Urls":[{"Link":"https://go.drugbank.com/drugs/DB00610","Name":"Metaraminol","Sub":false}]},{"Name":"PubChem","Urls":[{"Link":"https://pubchem.ncbi.nlm.nih.gov/compound/5906","Name":"Metaraminol","Sub":false}]},{"Name":"ChEMBL","Urls":[{"Link":"https://www.ebi.ac.uk/chembl/explore/compound/CHEMBL1201319","Name":"Metaraminol","Sub":false}]},{"Name":"ChEBI","Urls":[{"Link":"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:6794","Name":"Metaraminol","Sub":false}]},{"Name":"Common Chemistry","Urls":[{"Link":"https://commonchemistry.cas.org/detail?cas_rn=54-49-9","Name":"Metaraminol","Sub":false}]},{"Name":"HMDB","Urls":[{"Link":"https://hmdb.ca/metabolites/HMDB0014748","Name":"Metaraminol","Sub":false}]},{"Name":"KEGG","Urls":[{"Link":"https://www.kegg.jp/entry/C07146","Name":"Metaraminol","Sub":false}]},{"Name":"UNII","Urls":[{"Link":"https://gsrs.ncats.nih.gov/ginas/app/ui/substances/818U2PZ2EH","Name":"Metaraminol","Sub":false}]},{"Name":"EPA DSSTox","Urls":[{"Link":"https://comptox.epa.gov/dashboard/chemical/details/DTXSID8023268","Name":"Metaraminol","Sub":false}]}],"SMILES":"C[C@@H]([C@@H](C1=CC(=CC=C1)O)O)N","Salts":["bitartrate"],"SaltsAcidCount":[0],"SaltsAmineCount":[1],"SaltsUNII":["ZC4202M9P3"],"Scheduling":[{"gov":"Australia","schedule":"S4 substance"},{"gov":"United Kingdom","schedule":"prescription only substance"},{"gov":"United States","schedule":"prescription only substance"}],"Solubility":"SOLUBILITY IN ALCOHOL: 1 G/100 ML /BITARTRATE/","StoreUNII":["818U2PZ2EH"],"StructureBase64":"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Uses":"Adrenergic alpha-Agonists; Adrenergic Agents; Sympathomimetics; Vasoconstrictor Agents","Title":"Metaraminol","UNII":"818U2PZ2EH","Wikidata":"Q409981","Wikipedia":"Metaraminol","XLogP":-0.4}