盐酸酚苄明

盐酸酚苄明

中文名称盐酸酚苄明
中文同义词N-(1-甲基-2-苯氧乙基)-N-(2-氯乙基)苯甲胺盐酸盐;盐酸苯氧苄胺;盐酸酚苄明;苯苄胺;苯氧苄胺;酚苄胺;酚苄明盐酸盐;N-(2-氯乙基)-N-(1-甲基-2-苯氧乙基)苄胺盐酸盐
英文名称Phenoxybenzamine hydrochloride
英文同义词Benzenemethanamine, N-(2-chloroethyl)-N-(1-methyl-2-phenoxyethyl)-, hydrochloride;PHENOXYBENZAMINEHYDROCHLORIDE,USP;Bensylyt;BENZYLAMINE,N-(2-CHLOROETHYL)-N-(1-METHYL-2-PHENOXYETHYL)-HYDROCHLORIDE;fenossibenzamina;fenoxybenzamin;n-(2-chloroethyl)-n-(1-methyl-2-phenoxyethyl)-benzenemethanaminhydrochlo;n-(2-chloroethyl)-n-(1-methyl-2-phenoxyethyl)-benzylaminhydrochloride
CAS号63-92-3
分子式C18H22ClNO.ClH
分子量340.29
EINECS号200-569-7
相关类别原料药;医药原料;G蛋白偶联受体&G蛋白;中间体;小分子抑制剂;Amines;Aromatics;DIBENZYLINE;医用原料;细胞生物学试剂;科研试剂;原料;化学试剂;日用化学品;医药原料药;Intermediates & Fine Chemicals;Pharmaceuticals
Mol文件63-92-3.mol
结构式盐酸酚苄明 结构式

盐酸酚苄明 性质

熔点137.5°C
储存条件15-25°C
溶解度溶于乙醇、DMSO、二甲基甲酰胺(DMF)等有机溶剂。
酸度系数(pKa)pKa 4.4 (Uncertain)
形态粉末
颜色白色
水溶解性<0.01 g/100 mL at 18.5 ºC
Merck14,7256
稳定性自购买之日起 2 年内保持稳定。 DMSO 或蒸馏水中的溶液可在 -20°C 下储存长达 3 个月。
InChI1S/C18H22ClNO.ClH/c1-16(15-21-18-10-6-3-7-11-18)20(13-12-19)14-17-8-4-2-5-9-17;/h2-11,16H,12-15H2,1H3;1H
InChIKeyVBCPVIWPDJVHAN-UHFFFAOYSA-N
SMILESCl[H].CC(COc1ccccc1)N(CCCl)Cc2ccccc2
CAS 数据库63-92-3(CAS DataBase Reference)
(IARC)致癌物分类2B (Vol. 24, Sup 7) 1987
EPA化学物质信息N-(2-Chloroethyl)-N-(1-methyl-2-phenoxyethyl)benzylamine hydrochloride (63-92-3)

盐酸酚苄明 用途与合成方法

Phenoxybenzamine HCl (NSC 37448, NCI-c01661)是一种非选择性,不可逆α受体拮抗剂,IC50为550 nM。
TargetValue
α-adrenergic receptor

The IC 50 (100 nM) derived from the blockade of [ 3 H]yohimbine binding by Phenoxybenzamine hydrochloride is significantly less than the IC 50 (550 nM) for the corresponding reversal by Phenoxybenzamine hydrochloride of the effects of norepinephrine on cyclic AMP accumulation. Phenoxybenzamine hydrochloride (50 nM) in conbination with Phenoxybenzamine hydrochloridetolamine (1000 nM) enhances Phenoxybenzamine hydrochlorideylephrine-induced contraction compared with pretreatment with Phenoxybenzamine hydrochloride (50 nM) alone in endothelium-intact aortae. Combined treatment with either dexmedetomidine (300 or 1000 nM) and Phenoxybenzamine hydrochloride (50 nM) or Phenoxybenzamine hydrochloridetolamine (1000 nM) and Phenoxybenzamine hydrochloride (50 nM) enhance Phenoxybenzamine hydrochlorideylephrine-induced contraction compared with Phenoxybenzamine hydrochloride alone (50 nM). In addition, combined treatment with Phenoxybenzamine hydrochloridetolamine and Phenoxybenzamine hydrochloride enhances Phenoxybenzamine hydrochlorideylephrine-induced contraction compared with dexmedetomidine (1000 nM) and Phenoxybenzamine hydrochloride combined treatment. ​Combined treatment with high concentrations of dexmedetomidine (1000 nM) and Phenoxybenzamine hydrochloride enhances Phenoxybenzamine hydrochlorideylephrine-induced contraction compared with combined treatment with low concentrations of dexmedetomidine (300 nM) and Phenoxybenzamine hydrochloride. Phenoxybenzamine hydrochloride (0.1-100 μM) inhibits glioma proliferation, migration, and invasion and suppresses the tumorigenesis capacity. Phenoxybenzamine hydrochloride also inhibits self-renewal of glioma stem-like cells. Phenoxybenzamine hydrochloride activates LINGO-1 and inhibits the TrkB-Akt pathway. Phenoxybenzamine hydrochloride (0.1 μM-1 mM) preserves primary neurons within the CA1, CA3 and dentate gyrus and produces a robust neuroprotective effect, and prevents neuronal death from OGD in all regions of the hippocampus when delivered at 2, 4, and 8 h post-OGD at 100 μM.

Phenoxybenzamine hydrochloride (20 nM, s.c.) effectively suppresses the tumorigenesis of glioma cells in mice and the cell density in Phenoxybenzamine hydrochloride-U87MG xenografts decreases significantly. Phenoxybenzamine hydrochloride (1 mg/kg, i.v.) treated rats shows significant improvements in NSS and foot fault scoring.

化学性质 
白色结晶性粉末。熔点137.5-140℃。溶于乙醇、氯仿、丙二醇,略溶于苯,微溶于冷水。其游离碱熔点38-40℃,溶于苯。
用途 
α-受体阴断剂,选择性强,作用持久。主要用于嗜铬细胞瘤、雷诺氏综合症、物足发绀及冻疮后遗症。
用途 
用于治疗嗜铬细胞瘤、雷诺氏综合症、手足发绀及冻疮后遗症等
生产方法 
2-[benzyl(1-methyl-2-phenoxyethyl)amino]ethanol

101-45-1

盐酸酚苄明

63-92-3

在25-30℃条件下,将N-(苯氧基异丙基)-N-苄基乙醇胺溶解于二氯甲烷(810 mL)中。随后,在0-5℃下缓慢滴加亚硫酰氯(70.0 g, 0.588 mol)。反应混合物于25-30℃持续搅拌2小时。反应完成后,于30-35℃下进行减压浓缩。将浓缩后的残余物于25-30℃溶解于丙酮(570 mL)中,促使固体形成。通过过滤收集固体,并用冷却的丙酮(190 mL)洗涤。最后,将固体于45-50℃下进行真空干燥,得到125.4 g高纯度的苯氧基苯甲胺盐酸盐,呈白色固体(HPLC纯度 > 99%)。

参考文献:

[1] Patent: WO2018/130942, 2018, A1. Location in patent: Page/Page column 10; 12

安全信息

危险品标志Xn
危险类别码22-40
安全说明22-36/37/39-45
WGK Germany3
RTECS号DP3750000
海关编码2922299000
存储类别11 - 可燃固体
危险性类别急性毒性 类别4 经口
致癌性 类别2
更新日期产品编号产品名称CAS号包装价格
2025/12/22HY-B0431A盐酸酚苄明
Phenoxybenzamine hydrochloride
63-92-3500mg300元
2025/12/22HY-B0431A盐酸酚苄明
Phenoxybenzamine hydrochloride
63-92-310mM * 1mLin DMSO330元
"盐酸酚苄明"相关产品信息
甲磺隆 苯甲胺盐酸盐 二苯甲胺 三甲胺盐酸盐 1-金刚烷乙胺 甲基纤维素 苄嘧磺隆 苯甲醇 α-氨基乙苯 盐酸拓扑替康 尼泊金甲酯 乙酸苄酯 羟乙基甲基纤维素 苄胺 甲氧苄啶 甲醇 盐酸苯海拉明 丙烯酸甲酯
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