[(2S)-2-hydroxy-3-(naphthalen-1-yloxy)propyl](propan-2-yl)amine hydrochloride

• ChemBase编号: 133757
• 分子式: C16H22ClNO2
• 平均质量: 295.80438
• 单一同位素质量: 295.13390663
• SMILES: CC(C)NC[C@@H](COc1cccc2c1cccc2)O.Cl
• Canonical SMILES: O[C@H](COc1cccc2c1cccc2)CNC(C)C.Cl
• InChI: InChI=1S/C16H21NO2.ClH/c1-12(2)17-10-14(18)11-19-16-9-5-7-13-6-3-4-8-15(13)16;/h3-9,12,14,17-18H,10-11H2,1-2H3;1H/t14-;/m0./s1
• InChIKey: ZMRUPTIKESYGQW-UQKRIMTDSA-N

名称和登记号

名称

• IUPAC标准名: [(2S)-2-hydroxy-3-(naphthalen-1-yloxy)propyl](propan-2-yl)amine hydrochloride
• IUPAC传统名: [(2S)-2-hydroxy-3-(naphthalen-1-yloxy)propyl](isopropyl)amine hydrochloride
• 别名: (S)-1-异丙基氨基-3-(1-萘氧基)-2-丙醇 盐酸盐; (S)-(-)-普奈洛尔 盐酸盐; (S)-1-Isopropylamino-3-(1-naphthyloxy)-2-propanol hydrochloride; (S)-(-)-Propranolol hydrochloride; (2S)-1-[(1-Methylethyl)amino]-3-(1-naphthalenyloxy)-2-propanol Hydrochloride; S-(-)-1-Isopropylamino-3-(1-naphthoxy)-2-propanol Hydrochloride; (-)-Propranolol Hydrochloride; (S)-(-)-Propranolol Hydrochloride; L-(-)-Propranolol Hydrochloride; l-Propranolol Chlorhydrate; l-Propranolol Hydrochloride; (S)-Propranolol Hydrochloride

登记号

• CAS号: 4199-10-4
• EC号: 224-096-0
• MDL号: MFCD00064547
• Beilstein号: 3574966
• PubChem SID: 162228034; 24278657; 24887925
• PubChem CID: 165193

理论计算性质

• Acid pKa: 14.08793
• 质子受体: 3
• 质子供体: 2
• LogD (pH = 5.5): -0.6095358
• LogD (pH = 7.4): 0.3584574
• Log P: 2.583696
• 摩尔折射率: 76.8257 cm^3
• 极化性: 31.766071 Å^3
• 极化表面积: 41.49 Å^2
• 可自由旋转的化学键: 6
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: 45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: soluble8.0 mg/mL; DMSO: <14.5 mg/mL; ethanol: soluble10 mg/mL; H2O: soluble50 mg/mL (With heat. Aqueous solutions are most stable at pH 3.0 and decompose rapidly at basic pH. Decomposition is accompanied by discoloration of the solution.)
• 外观: powder
• 熔点: 193-195 °C(lit.); 193-197 °C
• 比旋光度: [α]20/D -25±2°, c = 1% in ethanol; [α]20/D -26°, c = 1 in ethanol; [α]25/D -25.5°, c = 1.0 in ethanol(lit.)

安全信息

• 欧盟危险性物质标志: 有害性(Harmful) (Xn)
• 德国WGK号: 3
• 危险公开号: 20/21/22
• 安全公开号: 36
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H302-H312-H332
• GHS警示性声明: P280
• 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

• 相关基因信息: human ... ADRB1(153), ADRB2(154), ADRB3(155), HTR1A(3350), HTR1B(3351), HTR1D(3352), HTR1E(3354), HTR1F(3355)

产品相关信息

• 纯度: ≥98% (TLC); ≥99.0% (AT); 98%
• 级别: puriss.
• 光学纯度: enantiomeric ratio: ≥99:1 (HPLC)
• 线性分子式: C10H7OCH2CH(OH)CH2NHCH(CH3)2·HCl

详细说明

Sigma Aldrich - P8688

包装
100, 500 mg in glass bottle
Biochem/physiol Actions
Active β-adrenoceptor blocking enantiomer, as measured by inhibition of isoprenaline-induced tachycardia; Propranolol is also non-specific 5-HT1A, 5-HT1B and 5-HT1C serotonin receptor antagonist. The stereoselective association of mianserin and propranolol with the 5HT1A, 5HT1B and 5HT1C sites may prove useful in the characterization of these sites

Sigma Aldrich - 82066

Other Notes
β-adrenergic blocker1

Toronto Research Chemicals - P831795

The S-enantiomer of Propranolol (P831800). β-Adrenergic blocker. Antihypertensive; antianginal; antiarrhythmic (class II).

参考文献

• Bond, et al.: Nature, 213, 721 (1967)
• Hansteen, V., et al.: Br. Med. J., 284, 155 (1967)
• Diamond, S., et al.: J. Clin. Pharmacol., 28, 193 (1967)