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

• ChemBase编号: 492
• 分子式: C9H13NO2
• 平均质量: 167.20502
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: 3-[(1R,2S)-2-amino-1-hydroxypropyl]phenol
• IUPAC传统名: metaraminol
• 商标名: Aramine; Icoral B; Metaradrine; Pressonex; Pressorol
• 别名: Metaraminolum [Latin]; Metaraminolum [INN-Latin]; Metaraminol Bitartrate; M-Hydroxypropadrine; M-Hydroxyphenylpropanolamine; M-Hydroxy Norephedrine; L-Metaraminol; Hydroxynorephedrine; Metaraminol

登记号

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

理论计算性质

JChem

• Acid pKa: 9.031579
• 质子受体: 3
• 质子供体: 3
• LogD (pH = 5.5): -2.383171
• LogD (pH = 7.4): -1.2987354
• Log P: -0.045079757
• 摩尔折射率: 46.8936 cm^3
• 极化性: 18.594221 Å^3
• 极化表面积: 66.48 Å^2
• 可自由旋转的化学键: 2
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: -0.59
• LOG S: -1.12
• 溶解度: 1.28e+01 g/l

分子性质

理化性质

• 溶解度: 1000 g/L
• 疏水性(logP): 0.6

详细说明

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

参考文献

• 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