3-[(1R,2S)-2-amino-1-hydroxypropyl]phenol

• ChemBase ID: 492
• Molecular Formular: C9H13NO2
• Molecular Mass: 167.20502
• Monoisotopic Mass: 167.09462866
• SMILES: O[C@@H]([C@@H](N)C)c1cc(O)ccc1
• Canonical SMILES: C[C@@H]([C@@H](c1cccc(c1)O)O)N
• 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-[(1R,2S)-2-amino-1-hydroxypropyl]phenol
• IUPAC Traditional name: metaraminol
• Brand Name: Aramine; Icoral B; Metaradrine; Pressonex; Pressorol
• Synonyms: Metaraminolum [Latin]; Metaraminolum [INN-Latin]; Metaraminol Bitartrate; M-Hydroxypropadrine; M-Hydroxyphenylpropanolamine; M-Hydroxy Norephedrine; L-Metaraminol; Hydroxynorephedrine; Metaraminol

Database IDs

• CAS Number: 54-49-9
• PubChem SID: 160963955; 46505593
• PubChem CID: 5906

CALCULATED PROPERTIES

JChem

• Acid pKa: 9.031579
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): -2.383171
• LogD (pH = 7.4): -1.2987354
• Log P: -0.045079757
• Molar Refractivity: 46.8936 cm^3
• Polarizability: 18.594221 Å^3
• Polar Surface Area: 66.48 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -0.59
• LOG S: -1.12
• Solubility (Water): 1.28e+01 g/l

PROPERTIES

Physical Property

• Solubility: 1000 g/L
• Hydrophobicity(logP): 0.6

DETAILS

DrugBank - DB00610

• Drug Groups: approved
• Description: 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. [PubChem]
• Indication: For the treatment and prevention of hypotension due to hemorrhage, spinal anesthesia, and shock associated with brain damage
• Pharmacology: 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 α1-adrenergic receptors but appears to have no effect on β-adrenergic receptors. It acts by increasing the force of the heart's pumping action as well as constricting peripheral blood vessels.
• Toxicity: LD₅₀=240 mg/kg (rat, oral); LD₅₀=99 mg/kg (mouse, oral)
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic
• Absorption: The effect starts 1-2 min after IV injection, 10 min after IM injection, 5-20 min after subcutaneous injection.
• Protein Binding: Approximately 45%
• References: McDonald M, Santucci RA: Successful management of stuttering priapism using home self-injections of the alpha-agonist metaraminol. Int Braz J Urol. 2004 Mar-Apr;30(2):121-2. [Pubmed] ; Koga S, Shiraishi K, Saito Y: Post-traumatic priapism treated with metaraminol bitartrate: case report. J Trauma. 1990 Dec;30(12):1591-3. [Pubmed] ; Block T, Sturm W, Ernst G, Staehler G, Schmiedt E: [Metaraminol in therapy of various forms of priapism] Urologe A. 1988 Jul;27(4):225-9. [Pubmed]
• External Links: Wikipedia; RxList

REFERENCES

• McDonald M, Santucci RA: Successful management of stuttering priapism using home self-injections of the alpha-agonist metaraminol. Int Braz J Urol. 2004 Mar-Apr;30(2):121-2. Pubmed
• Koga S, Shiraishi K, Saito Y: Post-traumatic priapism treated with metaraminol bitartrate: case report. J Trauma. 1990 Dec;30(12):1591-3. Pubmed
• Block T, Sturm W, Ernst G, Staehler G, Schmiedt E: [Metaraminol in therapy of various forms of priapism] Urologe A. 1988 Jul;27(4):225-9. Pubmed