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化合物简介
Cinnarizine is a medication derivative of piperazine, and characterized as an antihistamine and a calcium channel blocker, it is also known to promote cerebral blood flow, and so is used to treat cerebral apoplexy, post-trauma cerebral symptoms, and cerebral arteriosclerosis. However, it is more commonly prescribed for nausea and vomiting due to motion sickness or other sources such as chemotherapy, vertigo, or Ménière's disease. Cinnarizine was first synthesized by Janssen Pharmaceutica in 1955. The nonproprietary name is derived from the cinnamyl substituent on one of the nitrogen atoms, combined with the generic ending \"-rizine\" for \"antihistaminics/cerebral (or peripheral) vasodilators\". It is not available in the United States or Canada. It is manufactured and marketed in Bangladesh under the trade name Suzaraon by Rephco Pharmaceuticals Limited. It has also been cited as one of the most used drugs for seasickness within the British Royal Navy.
基本信息
CAS:298-57-7
中文别名:1-反式-肉桂基-4-二苯基甲基哌嗪;1-二苯甲基-4-(3-苯基-2-丙烯基)哌嗪;肉桂嗪;
英文别名:1-trans-Cinnamyl-4-diphenylmethylpiperazine;Stugeron;Cinnarizine;
分子式:C26H28N2
分子量:368.514
精确质量:368.225
Psa:6.48
Logp:4.9828
中文别名:1-反式-肉桂基-4-二苯基甲基哌嗪;1-二苯甲基-4-(3-苯基-2-丙烯基)哌嗪;肉桂嗪;
英文别名:1-trans-Cinnamyl-4-diphenylmethylpiperazine;Stugeron;Cinnarizine;
分子式:C26H28N2
分子量:368.514
精确质量:368.225
Psa:6.48
Logp:4.9828
编号系统
UNII:3DI2E1X18L
物化性质
外观与性状:白色粉末
密度:1.093g/cm3
沸点:509.2ºC at 760mmHg
熔点:117-120ºC
闪点:229.8ºC
折射率:1.649
储存条件:Refrigerator
蒸汽压:2.35E-10mmHg at 25°C
密度:1.093g/cm3
沸点:509.2ºC at 760mmHg
熔点:117-120ºC
闪点:229.8ºC
折射率:1.649
储存条件:Refrigerator
蒸汽压:2.35E-10mmHg at 25°C
安全信息
RTECS号:TL3430000
安全说明:S22; S24/25; S36; S26
WGK Germany:2
危险类别码:R20/22
海关编码:2933599090
危险品标志:Xn
安全说明:S22; S24/25; S36; S26
WGK Germany:2
危险类别码:R20/22
海关编码:2933599090
危险品标志:Xn
生产方法及用途
生产方法
由无水哌嗪与溴代二苯甲烷制取二苯甲基哌嗪,再与苯丙烯氯缩合而得。二苯甲烷在光照下加热,滴加溴素,在130℃保温1h,即得溴代二苯甲烷,C13H11Br,[776-74-9],熔点45℃。将溴代二苯甲烷滴加到哌嗪甲苯液中,于80-90℃搅拌3h,冷却后用水洗涤反应液,再用10%稀盐酸萃取,将酸层碱化析出沉淀,过滤烘干,得二苯甲基哌嗪。将其溶解在95%乙醇中,加入碳酸钠,在65℃左右滴加苯丙烯氯,滴完后,加热回流4h,趁热过滤,滤液放置过液,析出结晶,过滤,得脑益嗪粗品,经精制,得熔点117-119℃的成品。以二苯甲烷计,总收率48.2%。 长效多功能的血管收缩拮抗剂,能扩张血管,改善血循环,预防血管脆化,可用于治疗脑血管疾病,对颈性眩晕等引起的头痛,头晕失眠、记忆力减退,偏瘫,肢体麻木无力,言语不清等症也有疗效。
用途
长效多功能的血管收缩拮抗剂,能扩张血管,改善血循环,预防血管脆化,可用于治疗脑血管疾病,对颈性眩晕等引起的头痛,头晕失眠、记忆力减退,偏瘫,肢体麻木无力,言语不清等症也有疗效。
由无水哌嗪与溴代二苯甲烷制取二苯甲基哌嗪,再与苯丙烯氯缩合而得。二苯甲烷在光照下加热,滴加溴素,在130℃保温1h,即得溴代二苯甲烷,C13H11Br,[776-74-9],熔点45℃。将溴代二苯甲烷滴加到哌嗪甲苯液中,于80-90℃搅拌3h,冷却后用水洗涤反应液,再用10%稀盐酸萃取,将酸层碱化析出沉淀,过滤烘干,得二苯甲基哌嗪。将其溶解在95%乙醇中,加入碳酸钠,在65℃左右滴加苯丙烯氯,滴完后,加热回流4h,趁热过滤,滤液放置过液,析出结晶,过滤,得脑益嗪粗品,经精制,得熔点117-119℃的成品。以二苯甲烷计,总收率48.2%。 长效多功能的血管收缩拮抗剂,能扩张血管,改善血循环,预防血管脆化,可用于治疗脑血管疾病,对颈性眩晕等引起的头痛,头晕失眠、记忆力减退,偏瘫,肢体麻木无力,言语不清等症也有疗效。
用途
长效多功能的血管收缩拮抗剂,能扩张血管,改善血循环,预防血管脆化,可用于治疗脑血管疾病,对颈性眩晕等引起的头痛,头晕失眠、记忆力减退,偏瘫,肢体麻木无力,言语不清等症也有疗效。
合成路线
上游原料
下游产品
图谱
Predict 1H proton NMR

13C NMR : Predict

1H NMR : Predict

Mass spectrum (electron ionization)
