Metaraminol

Metaraminol
Systematic (IUPAC) name
	(1R,2S)-3-[-2-amino-1-hydroxy-propyl]phenol
Clinical data
AHFS/Drugs.com	International Drug Names
Pregnancy; category	AU: C; US: C (Risk not ruled out); ;
Legal status	UK: POM (Prescription only);
Routes of; administration	Intravenous
Pharmacokinetic data
Bioavailability	n/a
Protein binding	~45%
Metabolism	Hepatic
Identifiers
CAS Number	54-49-9 ; 33402-03-8 (bitartrate)
ATC code	C01CA09
PubChem	CID 5906
IUPHAR/BPS	7229
DrugBank	DB00610
ChemSpider	5695
UNII	818U2PZ2EH
KEGG	D08192
ChEBI	CHEBI:6794
ChEMBL	CHEMBL1201319
Chemical data
Formula	C9H13NO2
Molar mass	167.205 g/mol
	SMILES O[C@H](c1cc(O)ccc1)[C@@H](N)C ;
	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 ; Key:WXFIGDLSSYIKKV-RCOVLWMOSA-N ;
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Metaraminol (INN; trade names Aramine, Metaramin, and Pressonex), also known as metaradrine, a stereoisomer of meta-hydroxynorephedrine (3,β-dihydroxyamphetamine), is a potent sympathomimetic amine used in the prevention and treatment of hypotension, particularly as a complication of anesthesia. It is an α₁-adrenergic receptor agonist with some β effect.^[1]

Metaraminol is also used in the treatment of priapism. Although not approved for this use, it appears to be effective.^[2]^[3]^[4]

References[edit]

^ Kee VR. Hemodynamic pharmacology of intravenous vasopressors. Crit Care Nurse. 2003 Aug;23(4):79-82. PMID 12961786
^ McDonald M, Santucci R (2004). "Successful management of stuttering priapism using home self-injections of the alpha-agonist metaraminol.". Int Braz J Urol 30 (2): 121–2. doi:10.1590/S1677-55382004000200007. PMID 15703094.
^ Koga S, Shiraishi K, Saito Y (1990). "Post-traumatic priapism treated with metaraminol bitartrate: case report.". J Trauma 30 (12): 1591–3. doi:10.1097/00005373-199012000-00029. PMID 2258979.
^ Block T, Sturm W, Ernst G, Staehler G, Schmiedt E (1988). "[Metaraminol in therapy of various forms of priapism]". Urologe A 27 (4): 225–9. PMID 3140463.

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