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(+/-)-Verapamil hydrochloride

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(+/-)-Verapamil hydrochloride Basic information
(+/-)-Verapamil hydrochloride Chemical Properties
  • Melting point:142 °C (dec.)(lit.)
  • Density 1.0596 (rough estimate)
  • refractive index 1.6290 (estimate)
  • Flash point:9℃
  • storage temp. 2-8°C
  • solubility H2O: >30 mg/mL
  • pka8.6(at 25℃)
  • form solid
  • color white
  • Water Solubility soluble
  • Merck 14,9950
  • BRN 3647093
  • CAS DataBase Reference152-11-4(CAS DataBase Reference)
Safety Information
  • Hazard Codes T,F
  • Risk Statements 25-23/24/25-39/23/24/25-11
  • Safety Statements 45-36/37/39-36/37-16
  • RIDADR UN 2811 6.1/PG 3
  • WGK Germany 3
  • RTECS YV8320000
  • 8-10
  • HazardClass 6.1(b)
  • PackingGroup III
  • HS Code 29269090
  • ToxicityLD50 in mice, rats (mg/kg): 7.6, 16 i.v.; 68, 107 s.c.; 68, 67 i.p.; 163, 114 orally (Haas, Hrtfelder)
MSDS
(+/-)-Verapamil hydrochloride Usage And Synthesis
  • Chemical Propertieswhite to off-white powder
  • OriginatorIsoptin,Knoll ,W. Germany ,1963
  • Usesanalgesic, antipyretic
  • UsesBromhexine metabolite, sodium channel blocker, decongestent secretolytic agent for respiratory diseases
  • Manufacturing Process177.2 g (1 mol) of veratryl cyanide are dissolved in 1 liter of toluene in a three-neck flask. 42.9 g (1.1 mols) of pulverized sodium amide are added. The mixture is heated to boiling under reflux for one hour while stirring and excluding moisture. A solution of the base (N-methyl-N-homoveratryl)-γ- aminochloropropane, freshly prepared from 339.2 g (1.1 mols) of the hydrochloride, in 1.2 liters of toluene is added drop by drop into this boiling mixture within two hours while stirring vigorously. Heating and stirring are continued for four more hours. After cooling, the reaction mixture is poured into 3 liters of ice water while stirring, The mixture is acidified with 20% hydrochloric acid. The acidified aqueous layer is separated, neutralized by the addition of sodium hydroxide solution, and rendered alkaline by the addition of concentrated potassium carbonate solution. The precipitated oily base is taken up in benzene. On evaporating the solvent, 402 g of the crude base are obtained in the form of a reddish-brown, viscous oil.
    The crude base is dissolved in a mixture of 550 ml of isopropanol and 650 ml of ethyl acetate; Gaseous hydrogen chloride is introduced into the solution until it is of weakly acidic reaction. On allowing the mixture to stand at 0°C, 365 g of α-[(N-methyl-N-homoveratryl)-γ-amino-propyl]-3,4-dimethoxyphenyl acetonitrile hydrochloride precipitate as a slightly yellowish crystal powder of the melting point 136°C to 139°C (corr.). Yield: 81% of the theoretical yield. The pure, white hydrochloride melting at 140°C to 142°C (corr.) is obtained on recrystallizing the crude salt twice from isopropanol with the addition of decolorizing carbon. The salt is very soluble in water. The base prepared from the hydrochloride in the form of an almost colorless, very viscous oil boils at 233°C to 235°C/0.01 mm Hg; nD25= 1.5532. Dioxalate, melting point: 123°C to 125°C (corr.), on recrystallization from acetone and isopropanol.
    61.9 g (0.15 mol) of α-[(N-methyl-N-homoveratryl)-γ-aminopropyl]-3,4- dimethoxyphenyl acetonitrile are dissolved in 300 ml of toluene. The solution is heated to boiling under reflux with 8.5 g (1.45 x 0.15 mols) of pulverized sodium amide for one hour while stirring. Thereafter, a solution of 31.4 g (1.7 x 0.15 mols) of isopropyl bromide in 50 ml of toluene is added drop by drop thereto within 90 minutes and the mixture is kept boiling for four more hours while stirring. The cooled reaction mixture is allowed to run into 1.5 liters of ice water and the mixture is acidified with 20% hydrochloric acid. The aqueous layer is separated and is rendered alkaline by the addition of a solution of potassium carbonate. The base is taken up in warm benzene. The solvent is evaporated and the residue is distilled in a vacuum. 62.6 g of α- isopropyl-α-[(N-methyl-N-homoveratryl)-γ-aminopropy]-3,4-dimethoxyphenyl acetonitrile are obtained in the form of a light yellow, very viscous oil. Boiling point: 232°C to 235°C/0.01 mm Hg; n D 25 = 1.5460. Yield: 91.8% of the theoretical yield. Hydrochloride: melting point: 139.5°C to 140.5°C (corr.), on recrystallization from a mixture of isopropanol and ethyl acetate.
  • brand nameCalan (Searle); Covera (Searle); Isoptin (FSC); Isoptin (Par); Verelan (Elan).
  • Therapeutic Function Coronary vasodilator, Antiarrhythmic
  • Biological ActivityL-type calcium channel blocker. Vasodilator, adrenergic antagonist.
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