(1R,2S)-2-(methylamino)-1-phenylpropan-1-ol

• ChemBase编号: 1189
• 分子式: C10H15NO
• 平均质量: 165.2322
• 单一同位素质量: 165.11536411
• SMILES: O[C@@H]([C@@H](NC)C)c1ccccc1
• Canonical SMILES: CN[C@H]([C@@H](c1ccccc1)O)C
• InChI: InChI=1S/C10H15NO/c1-8(11-2)10(12)9-6-4-3-5-7-9/h3-8,10-12H,1-2H3/t8-,10-/m0/s1
• InChIKey: KWGRBVOPPLSCSI-WPRPVWTQSA-N

名称和登记号

名称

• IUPAC标准名: (1R,2S)-2-(methylamino)-1-phenylpropan-1-ol
• IUPAC传统名: ephedrine
• 别名: (1R,2S)-2-甲氨基-苯丙烷-1-醇; (-)-麻黄碱; (-)-麻黄碱; (1R,2S)-(-)-α-(1-甲基氨基乙基)苄醇; (1R,2S)-(-)-2-甲氨基-1-苯丙醇; L-盐酸麻黄碱; (1R,2S)-(-)-麻黄碱; (1R,2S)-2-Methylamino-1-phenyl-1-propanol; (-)-Ephedrine; (1R,2S)-(-)-Ephedrine Sulfate; (αR)-,α-[(1S)-1-(Methylamino)ethyl]benzenemethanol Hemisulfate; (-)-erythro-1-Hydroxy-2-(methylamino)-1-phenylpropane Sulfate; (-)-Ephedrine Sulfate; (1R,2S)-1-Phenyl-2-methylaminopropanol-1 Sulfate; Ephedrine Sulphate; Isofedrol; l-Ephedrine Sulfate; (-)-erythro-Ephedrine Sulfate; Ephedrine; (-)-Ephedrine; (1R,2S)-(-)-α-(1-Methylaminoethyl)benzyl alcohol; (1R,2S)-(-)-2-Methylamino-1-phenyl-1-propanol; L-α-(1-Methylaminoethyl)benzyl alcohol; (1R,2S)-(-)-Ephedrine

登记号

• CAS号: 299-42-3; 134-72-5
• EC号: 206-080-5
• MDL号: MFCD00064257
• Beilstein号: 2208730
• PubChem SID: 46507538; 24848190; 160964651; 24868714
• PubChem CID: 9294; 5032
• CHEBI ID: 15407
• ATC码: R01AB05; R03CA02; C01CA26; QG04BX90; R01AA03; S01FB02
• CHEMBL: 211456
• Chemspider ID: 8935
• DrugBank ID: DB01364
• IUPHAR配体索引: 556
• KEGG ID: D00124
• 美国药典/FDA物质标识码: GN83C131XS
• 维基百科标题: Ephedrine

理论计算性质

JChem

• Acid pKa: 13.889531
• 质子受体: 2
• 质子供体: 2
• LogD (pH = 5.5): -1.8580045
• LogD (pH = 7.4): -0.7786886
• Log P: 1.3178347
• 摩尔折射率: 49.6873 cm^3
• 极化性: 19.85273 Å^3
• 极化表面积: 32.26 Å^2
• 可自由旋转的化学键: 3
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 1.0
• LOG S: -1.3
• 溶解度: 8.26e+00 g/l

分子性质

理化性质

• 溶解度: 63.6 mg/mL at 30 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]
• 熔点: ~36 °C; 37-39 °C(lit.)
• 沸点: 255 °C(lit.)
• 闪点: 186.8 °F; 86 °C
• 密度: 1.124 g/mL at 25 °C(lit.)
• 比旋光度: [α]20/D -42±1°, c = 4.5% in 2% HCl; [α]21/D -41°, c = 5 in 1 M HCl
• 疏水性(logP): 1.13 [AVDEEF,A (1997)]

安全信息

• RTECS编号: KB0700000
• 欧盟危险性物质标志: 有害性(Harmful) (Xn)
• 德国WGK号: 1
• 危险公开号: 22
• 安全公开号: 22-25
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H302
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves
• 保存温度: 2-8°C

药理学性质

• 给药途径: oral, IV, IM, SC
• 生物利用度: 85%
• 排泄: 22-99% renal
• 半衰期: 3–6 hours
• 代谢: minimal hepatic
• 法定药品分级: Behind the Counter (BTC) (US); P (UK); S4 (Australia); Schedule VI (Canada)
• 妊娠期药物分类: A (Australia); A (US)

产品相关信息

• 纯度: ≥98.0% (NT); 98%
• 级别: purum
• 杂质: ≤0.5% water
• 线性分子式: C6H5CH[CH(NHCH3)CH3]OH
• Empirical Formula (Hill Notation): C10H15NO

详细说明

DrugBank - DB01364

• Drug Groups: approved
• Description: An alpha- and beta-adrenergic agonist that may also enhance release of norepinephrine. It has been used in the treatment of several disorders including asthma, heart failure, rhinitis, and urinary incontinence, and for its central nervous system stimulatory effects in the treatment of narcolepsy and depression. It has become less extensively used with the advent of more selective agonists. [PubChem]
• Indication: Ephedrine commonly used as a stimulant, appetite suppressant, concentration aid, decongestant, and to treat hypotension associated with anaesthesia.
• Pharmacology: Ephedrine is similar in structure to the derivatives amphetamine and methamphetamine. Chemically, it is an alkaloid derived from various plants in the genus Ephedra (family Ephedraceae). It works mainly by increasing the activity of noradrenaline on adrenergic receptors.
• Toxicity: Cardiovascular: tachycardia, cardiac arrhythmias, angina pectoris, vasoconstriction with hypertension
• Absorption: 85%
• Half Life: 3-6 hours
• Elimination: mainly renal
• External Links: Wikipedia; RxList; Drugs.com

Sigma Aldrich - 134910

包装
5, 25, 100 g in glass bottle
Application
通用手性合成子，1用于催化2以及制备光学纯亚砜3和噁唑烷。4

Sigma Aldrich - 45261

Other Notes
可能实行销售限制

Toronto Research Chemicals - E575010

(-)-erythro-Ephedrine Sulfate is the sulfate salt of the α- and β-adrenergic agonist Ephedrine. (-)-erythro-Ephedrine is a sympathomimetic amine with stimulant properties. (-)-erythro-Ephedrine Sulfate is a bronchodilator used in the treatment of asthma.

参考文献

• Familiar, R.G. et al.: J. Pharmac. Sci, 56, 768 (1967)
• Weinberger, M. et al.: J. Pediat., 84, 421 (1967)
• Vidrio, H. et al.: J. Pharmacol. Exp. Therap., 187, 308 (1967)