Metaraminol
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|---|---|
| Systematic (IUPAC) name | |
| (1R,2S)-3-[-2-amino-1-hydroxy-propyl]phenol | |
| Clinical data | |
| AHFS/Drugs.com | International Drug Names |
| Pregnancy cat. | C(AU) C(US) |
| Legal status | POM (UK) |
| Routes | Intravenous |
| Pharmacokinetic data | |
| Bioavailability | n/a |
| Protein binding | ~45% |
| Metabolism | Hepatic |
| Identifiers | |
| CAS number | 54-49-9  |
| ATC code | C01CA09 |
| PubChem | CID 5906 |
| DrugBank | APRD00555 |
| ChemSpider | 5695 |
| UNII | 818U2PZ2EH |
| KEGG | D08192 |
| ChEBI | CHEBI:6794 |
| ChEMBL | CHEMBL1201319  |
| Chemical data | |
| Formula | C9H13NO2 |
| Mol. mass | 167.205 g/mol |
| SMILES | eMolecules & PubChem |
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Metaraminol (INN, trade name Aramine) 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]
[edit] Chemistry
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.
- 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.
- G. Erhart, L. Stein, DE 571229 (1930).
- G. Erhart, L. Stein, U.S. Patent 1,948,162 (1934).
- W. H. Hartung, U.S. Patent 1,995,709 (1935).
- I. G. Farbenindustrie AG, GB 396951 (1932).
[edit] See also
[edit] References
- ^ 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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