Verapamil 维拉帕米

CAS 52-53-9 MFCD00056240

化学结构图

52-53-9
SMILES: COc1ccc(CCN(C)CCCC(C#N)(c2ccc(OC)c(OC)c2)C(C)C)cc1OC

化学属性

Mol. FormulaC27H38N2O4
Mol. Weight454.67
Refractive index1.5448
Boiling Point243-246 °C (1.3 Pa)
Appearance 粘稠的淡黄色油状液体。沸点243-246℃（1.3Pa），折光率（nD25）1.5448。溶于苯、醚，易溶于低级醇、丙酮、乙酸乙酯、氯仿，难溶于已烷，不溶于水。其盐酸盐（[152-11-4]）为白色至类白色结晶性粉末。熔点138.5-140.5℃（分解）。易溶于甲醇、二甲基甲酰胺，溶于乙醇、异丙醇、丙酮、乙酸乙酯，不溶于氯仿。无臭，味苦。

别名和识别编码

Chemical NameVerapamil
MDL NumberMFCD00056240
Chemical Name Translation维拉帕米
Synonym alpha-[3-[[2-(3,4-dimethoxyphenyl)ethyl]-methylamino]propyl]-3,4-dimethoxy-alp alpha-((n-methyl-n-homoveratryl)-gamma-aminopropyl)-3,4-dimethoxyphenylaceto Benzeneacetonitrile, alpha-[3-[[2-(3,4-dimethoxyphenyl)ethyl]methylamino]propyl]-3,4-dimethoxy-alpha-(1-methylethyl)- 维拉帕米 VERAPAMIL Iproveratril -2-isopropyl- alpha-isopropyl-alpha-[(n-methyl-n-homoveratryl)-gamma-aminopropyl]-3,4-dimeth Dilacoran alpha-((N-Methyl-N-homoveratryl)-gamma-aminopropyl)-3,4-dimethoxyphenylacetonitrile (+/-) VERAPAMIL 5-((3,4-dimethoxyphenethyl)methylamino)-2-(3,4-dimethoxyphenyl)-2-isopropylval benzeneacetonitrile,alpha-(3-((2-(3,4-dimethoxyphenyl)ethyl)methylamino)propy eronitrile 2-(3,4-Dimethoxyphenyl)-5-[[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino]-2-isopropylpentanenitrile aleronitrile 5-((3,4-dimethoxyphenethyl)methylamino)-2-(3,4-dimethoxyphenyl)-2-isopropylv Verapamil 5-((3,4-二甲氧基苯乙基)甲基氨基)-2-(3,4-二甲氧基苯基)-2-异丙基戊腈 CP-16533-1 异博定 4-dimethoxy-alpha-(1-methylethyl)-l)- D-365 2-isopropyl- 戊脉胺 Vasolan Isoptin 5-((3,4-Dimethoxyphenethyl)methylamino)-2-(3,4-dimethoxyphenyl)-2-isopropylvaleronitrile
CAS Number52-53-9
EC Number200-145-1
Wiswesser Line Notation1OR BO1 DXCN&Y1&1&3N1&2R CO1 DO1
LabNetwork Molecule IDLN01346584
PubChem Substance ID2520
InChIInChI=1S/C27H38N2O4/c1-20(2)27(19-28,22-10-12-24(31-5)26(18-22)33-7)14-8-15-29(3)16-13-21-9-11-23(30-4)25(17-21)32-6/h9-12,17-18,20H,8,13-16H2,1-7H3
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相关文献及参考

  • [2]. Krikler DM. Verapamil in arrhythmia. Br J Clin Pharmacol. 1986;21 Suppl 2:183S-189S.
  • [3]. Rehnqvist N,et al. Effects of metoprolol vs verapamil in patients with stable angina pectoris. The Angina Prognosis Study in Stockholm (APSIS). Eur Heart J. 1996 Jan;17(1):76-81.
  • [4]. Kubo Y, et al. Blood-to-Retina Transport of Fluorescence-Labeled Verapamil at the Blood-Retinal Barrier. Pharm Res. 2018 Mar 12;35(5):93.
  • [5]. Zhou P, et al. Anti-arrhythmic effect of Verapamil is accompanied by preservation of cx43 protein in rat heart. PLoS One. 2013 Aug 12;8(8):e71567.
  • [1]. Gowarty JL, et al. Verapamil as a culprit of palbociclib toxicity. J Oncol Pharm Pract. 2019 Apr;25(3):743-746.
  • [1]. Gowarty JL, et al. Verapamil as a culprit of palbociclib toxicity. J Oncol Pharm Pract. 2019 Apr;25(3):743-746.
  • [2]. Krikler DM. Verapamil in arrhythmia. Br J Clin Pharmacol. 1986;21 Suppl 2:183S-189S.
  • [3]. Rehnqvist N,et al. Effects of m

安全信息

RTECSYV8300000 
TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Human - woman
DOSE/DURATION           : 80 mg/kg
TOXIC EFFECTS :
   Behavioral - coma
   Cardiac - pulse rate increase, without fall in BP
   Vascular - BP lowering not characterized in autonomic section
REFERENCE :
   HETOEA Human & Experimental Toxicology.  (Macmillan Press Ltd., Brunel Road,
   Houndmills, Basingstoke, Hampshire, RG21 2XS, UK) V.9- 1990-
   Volume(issue)/page/year: 16,35,1997

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Human - man
DOSE/DURATION           : 46 mg/kg
TOXIC EFFECTS :
   Sense Organs and Special Senses (Eye) - ptosis
   Cardiac - EKG changes not diagnostic of specified effects
   Vascular - BP lowering not characterized in autonomic section
REFERENCE :
   CTOXAO Clinical Toxicology.  (New York, NY)  V.1-18, 1968-81.  For publisher
   information, see JTCTDW.  Volume(issue)/page/year: 17,395,1980

TYPE OF TEST            : LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Human - man
DOSE/DURATION           : 83 mg/kg
TOXIC EFFECTS :
   Behavioral - convulsions or effect on seizure threshold
   Cardiac - cardiomyopathy including infarction
   Vascular - BP lowering not characterized in autonomic section
REFERENCE :
   AJEMEN American Journal of Emergency Medicine.  (WB Saunders, Philadelphia,
   PA)  V.1-    1983-  Volume(issue)/page/year: 7,624,1989

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intravenous
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 1520 ug/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   EJTXAZ European Journal of Toxicology and Environmental Hygiene.  (Paris,
   France)  V.7-

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - rat
DOSE                    : 60 mg/kg
SEX/DURATION            : female 10-12 day(s) after conception
TOXIC EFFECTS :
   Reproductive - Fertility - post-implantation mortality (e.g. dead and/or
   resorbed implants per total number of implants)
   Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death,
   e.g., stunted fetus)
   Reproductive - Specific Developmental Abnormalities - cardiovascular
   (circulatory) system
REFERENCE :
   REPTED Reproductive Toxicology.  (Pergamon Press Inc., Maxwell House,
   Fairview Park, Elmsford, NY 10523)  V.1-    1987-  Volume(issue)/page/year:
   11,207,1997

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Human - man
DOSE                    : 51 mg/kg
SEX/DURATION            : male 30 day(s) pre-mating
TOXIC EFFECTS :
   Reproductive - Paternal Effects - breast development
REFERENCE :
   MJAUAJ Medical Journal of Australia.  (Australasian Medical Pub. Co. Ltd.,
   71-79 Arundel St., Glebe, N.S.W., Australia)  V.1-    1914-
   Volume(issue)/page/year: 161,328,1994

其他信息

  • MOL 文件:52-53-9.mol
  • 方法一:二甲氧基苯乙腈与溴异丙烷进行烃化反应后，与1，3-氯溴丙烷进行氯丙基化反应，然后与3，4-二甲氧基苯乙胺缩合制成维拉帕米。
  • Sigma Aldrich:52-53-9(sigmaaldrich)
  • 上游原料:氰化苄 --> 苯甲醚 --> 2-溴丙烷 --> 正丙基溴 --> 3,4-二甲氧基苯乙胺
  • MSDS 信息:(2R)-2-(3,4-Dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-isopropylpentanenitrile(52-53-9).msds
  • 用途一:选择性冠脉扩张剂。主要用于阵发性室外上性心动过速，对心房纤颤或心房扑动仅能减慢心室率，仅有少数转为窦性心率，也用于心绞痛、高血压和肥厚型梗塞性心肌病。

系列性分类

  1. Medical Research Areas
  2. Metabolism
  3. Cytochrome P450  (细胞色素P450)

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