anipamil
anipamil Basic information
- Product Name:
- anipamil
- Synonyms:
-
- anipamil
- 2-Dodecyl-5-[3-methoxyphenethyl(methyl)amino]-2-(3-methoxyphenyl)pentanenitrile
- 2-(3-methoxyphenyl)-2-[3-[2-(3-methoxyphenyl)ethyl-methylamino]propyl]tetradecanenitrile
- Benzeneacetonitrile, α-dodecyl-3-methoxy-α-[3-[[2-(3-methoxyphenyl)ethyl]methylamino]propyl]-
- anipamil USP/EP/BP
- Anipamilum [Latin]
- CAS:
- 83200-10-6
- MF:
- C34H52N2O2
- MW:
- 520.79
- EINECS:
- 2802135
- Mol File:
- 83200-10-6.mol
anipamil Chemical Properties
- storage temp.
- Store at -20°C
- solubility
- Acetone (Slightly), Methanol (Slightly)
- form
- Thick Oil to Gel
- color
- Pale Yellow
anipamil Usage And Synthesis
Originator
Anipamil,Onbio Inc.
Uses
A long-acting analog of Verapamil (V125000) with antiarrhythmic and antihypertensive activity.
Manufacturing Process
1,7-Bis-(3-ethoxyphenyl)-3-methylaza-7-cyano-nonadecane:
0.06 mole of 1-cyano-1-(3-methoxyphenyl)tridecane (prepared by phase
transfer-catalyzed alkylation of 3-methoxyphenylacetonitrile with 1-
bromododecane) and 0.06 mole of 1-chloro-4-methylaza-6-(3-
methoxyphenyl)hexane [prepared from N-methyl-β-(3-
methoxyphenyl)ethylamine and 1-bromo-3-chloropropane by a method similar
to that described in Arzneim.-Forsch. 28 (II) (1978), 2048] were dissolved in
100 ml of dry toluene in a three-necked flask provided with a stirrer, dropping
funnel, reflux condenser and thermometer. 9.3 g (0.07 mole) of a 30%
strength suspension of sodium amide in toluene were then added dropwise at
from 100° to 110°C, with stirring, and stirring was continued under reflux for
a further 90 minutes.
The resulting reaction solution was poured into 200 ml of ice water, and the
toluene phase was separated off and washed twice with water. The required
amount of hydrochloric acid was added to the toluene solution, the toluene
was distilled off under reduced pressure and the residue, which remained was
recrystallized from acetone to give 1,7-bis-(2-methoxyphenyl)-3-methylaza-7-
cyanononadecane hydrochloride or α-dodecyl-3-methoxy-α-[3-[[2-(3-
methoxyphenyl)ethyl]methylamino]propyl]benzene-acetonitrile (anipamil);
MP: 60°-69.5°C.
Therapeutic Function
Coronary vasodilator, Antihypertensive
in vivo
Anipamil (40 mg, p.o.)-treated 2K-1C rabbits reveal absent or negligible intimal thickening and a decrease of postnatal-type SMC from the underlying media. Anipamil inhibits the growth of SMC accompanied by the expression of SM-MyHC in all SMC, ie, the appearance of a more differentiated cell phenotype compared to control cultures[1]. In the arrhythmic assay, anipamil (1.0 mg/kg + 0.10 mg/kg/min infusion, n=8 or 5.0 mg/kg + 0.50 mg/kg/min infusion, n=12) reduces VT but not VF[2]. In rats with subtotal (five-sixths) nephrectomy treated with anipamil (0.5 mg/kg/day, p.o.), the mortality is less, and the mean arterial blood pressure is also more well controlled, and the serum creatinine concentration is lower than control group. The anipamil (2 mg/kg/day)-treated group exhibits significantly greater protection of renal function than does the hydralazine-treated group for the same level of blood pressure control[3].
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