Metaraminol

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Metaraminol
Metaraminol Structural Formulae.png
Systematic (IUPAC) name
(1R,2S)-3-[-2-amino-1-hydroxy-propyl]phenol
Clinical data
AHFS/Drugs.com International Drug Names
Pregnancy cat.
Legal status
Routes Intravenous
Pharmacokinetic data
Bioavailability n/a
Protein binding ~45%
Metabolism Hepatic
Identifiers
CAS number 54-49-9 YesY
33402-03-8 (bitartrate)
ATC code C01CA09
PubChem CID 5906
DrugBank DB00610
ChemSpider 5695 YesY
UNII 818U2PZ2EH YesY
KEGG D08192 YesY
ChEBI CHEBI:6794 YesY
ChEMBL CHEMBL1201319 N
Chemical data
Formula C9H13NO2 
Mol. mass 167.205 g/mol
 N (what is this?)  (verify)

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.

Metaraminol is also used in the treatment of priapism. Although not approved for this use, it appears to be effective.[1][2][3]

Synthesis[edit]

Metaraminol, L-1-(3-hydroxyphenyl)-2-aminopropan-1-ol, is synthesized in two ways. The first way is synthetic, and it is from 3-hydroxypropiophenone. The hydroxyl group is protected by alkylation with benzyl chloride, giving 3-benzyloxypropiophenone. Upon reaction with butyl nitrite, it undergoes nitrosation into the isonitrosoketone, which by reduction using hydrogen over Raney nickel turns into 1-(3-benzyloxyphenyl)-2-aminopropan-1-ol, the protecting benzyl group is removed by reduction using hydrogen over palladium catalyst, to give racemic metaraminol. The desired L-isomer is isolated with the help of (+)-tartaric acid.

Metaraminol synthesis: G. Erhart, L. Stein, DE 555404  (1930). E. W. Zeh, U.S. Patent 1,951,229 (1934).

The second way is semisynthetic, consisting of fermentation of D-glucose in the presence of 3-acetoxybenzaldehyde, which forms (–)-1-hydroxy-1-(3-hydroxyphenyl)-acetone, the carbonyl group of which is reduced by hydrogen over a palladium catalyst in the presence of ammonia, giving metaraminol.

Metaraminol synthesis 2: Bockmuhl Max, Ehrhart Gustav, Stein Leonhard DE 571229  (1930). U.S. Patent 1,948,162 (1934). W. H. Hartung, U.S. Patent 1,995,709 (1935). IG Farben, GB 396951  (1932).

See also[edit]

References[edit]

  1. ^ 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. 
  2. ^ 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. 
  3. ^ 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.