3-(3-ethyl-1-methylazepan-3-yl)phenol hydrochloride

• ChemBase编号: 154801
• 分子式: C15H24ClNO
• 平均质量: 269.81016
• 单一同位素质量: 269.15464207
• SMILES: CCC1(CCCCN(C1)C)c1cccc(c1)O.Cl
• Canonical SMILES: CCC1(CCCCN(C1)C)c1cccc(c1)O.Cl
• InChI: InChI=1S/C15H23NO.ClH/c1-3-15(9-4-5-10-16(2)12-15)13-7-6-8-14(17)11-13;/h6-8,11,17H,3-5,9-10,12H2,1-2H3;1H
• InChIKey: MPJUSISYVXABBH-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 3-(3-ethyl-1-methylazepan-3-yl)phenol hydrochloride
• IUPAC传统名: meptazinol hydrochloride
• 别名: 3-(3-ethylhexahydro-1-methyl-1H-azepin-3-yl)-phenol hydrochloride; IL-22811 hydrochloride; WY-22811 hydrochloride; Meptazinol hydrochloride; 3-(3-Ethylhexahydro-1-methyl-1H-azepin-3-yl)phenol; 1-Methyl-3-ethyl-3-(m-hydroxy-phenyl)hexahydro-1H-azepine; Meptazinol Hydrochloride; Meptazinol HCl

登记号

• CAS号: 59263-76-2
• EC号: 261-683-0
• MDL号: MFCD00941476
• PubChem SID: 162248939
• PubChem CID: 65483

理论计算性质

• Acid pKa: 10.227932
• 质子受体: 2
• 质子供体: 1
• LogD (pH = 5.5): 0.16047607
• LogD (pH = 7.4): 1.5519505
• Log P: 3.0681393
• 摩尔折射率: 72.2777 cm^3
• 极化性: 28.251764 Å^3
• 极化表面积: 23.47 Å^2
• 可自由旋转的化学键: 2
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: DMSO; H2O: >10 mg/mL; Methanol; Water
• 外观: white to off-white powder; White to Off-WHite Solid
• 熔点: 250-252°C

安全信息

• 保存条件: Refrigerator
• RTECS编号: SL4250000
• 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
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H302

药理学性质

• 作用靶点: Others

产品相关信息

• 纯度: ≥98% (HPLC)
• 成盐信息: HCl
• Empirical Formula (Hill Notation): C15H23NO· HCl

详细说明

Sigma Aldrich - M2824

Biochem/physiol Actions
Meptazinol entered the human pharmaceutical market as a racemic mixture in the 1980s for use as an analgesic. Its pharmacology is not completely understood; however, its analgesic properties are mostly due to its partial agonism at the mu1 opioid receptor. Due to its partial agonism, Meptazinol antagonizes morphine dependence in vivo. Its advantage over other opiates is its reduced capacity to cause addition and respiratory depression, also due to its intrinsic activity as a partial agonist. Meptazinol has been found to have additional activity as an acetylcholinesterase (AChE) inhibitor, particularly in its (-) enantiomeric form, which may partially explain its analgesic properties. AChE inhibitors are used to treat Alzheimer′s disease, providing additional interest in this compound.

Toronto Research Chemicals - M225080

Mixed opioid agonist-antagonist. Analgesic (narcotic).

参考文献

• Davies, G., et al.: Eur. J. Clin. Pharmacol., 23, 535 (1982)
• Johnson, Holmes, B., et al.: Drugs, 30, 285 (1982)
• R.E., et al.: Clin. Pharmacol. Ther., 41, 426 (1982)