Verapamil HCl

Modify Date: 2024-01-02 23:12:54

Verapamil HCl Structure
Verapamil HCl structure
 Common Name Verapamil HCl
CAS Number 152-11-4 Molecular Weight 491.063
Density 1.058g/cm3 Boiling Point 586.1ºC at 760 mmHg
Molecular Formula C27H39ClN2O4 Melting Point 142 °C (dec.)(lit.)
MSDS Chinese USA Flash Point 308.3ºC
Symbol GHS06
GHS06		 Signal Word Danger

 Use of Verapamil HCl


Verapamil hydrochloride is a calcium channel antagonist.

 Names

Name (±)-Verapamil hydrochloride
Synonym More Synonyms

 Verapamil HCl Biological Activity

Description Verapamil hydrochloride is a calcium channel antagonist.
Related Catalog
Target

Calcium channel[1]

In Vitro Verapamil (hydrochloride) is an L-type calcium channel antagonist. The combination of Bortezomib and Verapamil (70 µM) markedly declines the viability of the JK-6L, RPMI 8226, and ARH-77 cell lines after 16 hours of culture[1]. The enzyme hydrolase activity of recombinant human carboxylesterase (CES2) is substantially inhibited by Verapamil with Ki of 3.84±0.99μM[2].
In Vivo Verapamil, a calcium channel antagonist, is injected i.v. into a femoral vein prior to ischemia. Verapamil (1 mg/kg) significantly decreases the incidence of ventricular arrhythmias including premature ventricular contractions (PVC), ventricular tachycardia (VT) and ventricular fibrillation (VF) for 45-min coronary artery occlusion. Total arrhythmia scores are significantly increased when the heart is subjected to ischemia (P<0.01 vs. sham). Verapamil (1 mg/kg) significantly prevented the enhancement of total arrhythmia scores induced by ischemia (P<0.01 vs. ischemia). Results indicate that Verapamil exerts an anti-arrhythmic property[3].
Cell Assay Cells (1×105) are treated with 10 nM Bortezomib and/or 70 µM Verapamil for 16 hours and incubated for another 4 hours with Alamar-Blue. Activity of the mitochondrial dehydrogenase results in conversion of the coloring, which is followed by measurement of the absorption using a spectrophotometer[1].
Animal Admin Rats[3] Adult male Sprague-Dawley (SD) rats (250−350 g) are used. Verapamil (1 mg/kg) is injected i.v. into a femoral vein 10 min prior to ischemia. A sham group undergoes the same surgical procedures, except the suture underneath the LAD is left untied. In another series of experiment, arrhythmia is induced by Bay K8644, an L-type calcium channel agonist, at a dose of 0.1 mg/kg given i.v. into the FV. Verapamil (1 mg/kg) is administered 10 min prior to Bay K8644. All injections are performed within 30 sec.
References

[1]. Meister S, et al. Calcium channel blocker Verapamil enhances endoplasmic reticulum stress and cell death induced by proteasome inhibition in myeloma cells. Neoplasia. 2010 Jul;12(7):550-61.

[2]. Yanjiao X, et al. Evaluation of the inhibitory effects of antihypertensive drugs on human carboxylesterase in vitro. Drug Metab Pharmacokinet. 2013;28(6):468-74.

[3]. 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.

 Chemical & Physical Properties

Density 1.058g/cm3
Boiling Point 586.1ºC at 760 mmHg
Melting Point 142 °C (dec.)(lit.)
Molecular Formula C27H39ClN2O4
Molecular Weight 491.063
Flash Point 308.3ºC
Exact Mass 490.259827
PSA 63.95000
LogP 5.89508
Storage condition Refrigerator (+4°C)
Water Solubility soluble

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
YV8320000
CHEMICAL NAME :
Valeronitrile, 5-((3,4-dimethoxyphenethyl)methylamino)-2-(3,4-dimeth oxyphenyl)-2-isopropy l-, monohydrochloride
CAS REGISTRY NUMBER :
152-11-4
LAST UPDATED :
199707
DATA ITEMS CITED :
32
MOLECULAR FORMULA :
C27-H38-N2-O4.Cl-H
MOLECULAR WEIGHT :
491.13
WISWESSER LINE NOTATION :
1OR BO1 DXCNY1&1&3N1&2R CO1 DO1 &GH

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
96 mg/kg
TOXIC EFFECTS :
Cardiac - pulse rate increase, without fall in BP Vascular - BP lowering not characterized in autonomic section Lungs, Thorax, or Respiration - acute pulmonary edema
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
72 mg/kg/14H-I
TOXIC EFFECTS :
Cardiac - EKG changes not diagnostic of specified effects Cardiac - pulse rate Vascular - BP lowering not characterized in autonomic section
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
58 mg/kg
TOXIC EFFECTS :
Cardiac - EKG changes not diagnostic of specified effects Vascular - BP lowering not characterized in autonomic section Lungs, Thorax, or Respiration - acute pulmonary edema
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - infant
DOSE/DURATION :
80 mg/kg
TOXIC EFFECTS :
Behavioral - coma Cardiac - pulse rate Lungs, Thorax, or Respiration - dyspnea
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
89 mg/kg
TOXIC EFFECTS :
Cardiac - arrhythmias (including changes in conduction) Vascular - BP lowering not characterized in autonomic section Nutritional and Gross Metabolic - changes in calcium
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
14400 ug/kg
TOXIC EFFECTS :
Vascular - regional or general arteriolar constriction
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
3429 ug/kg
TOXIC EFFECTS :
Cardiac - arrhythmias (including changes in conduction) Gastrointestinal - necrotic changes
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
135 mg/kg
TOXIC EFFECTS :
Sense Organs and Special Senses (Eye) - mydriasis (pupillary dilation) Behavioral - coma Lungs, Thorax, or Respiration - cyanosis
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
26 mg/kg
TOXIC EFFECTS :
Cardiac - pulse rate Vascular - BP lowering not characterized in autonomic section Lungs, Thorax, or Respiration - dyspnea
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
143 ug/kg/4H-C
TOXIC EFFECTS :
Vascular - BP lowering not characterized in autonomic section
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
68571 mg/kg
TOXIC EFFECTS :
Cardiac - arrhythmias (including changes in conduction) Cardiac - pulse rate Vascular - regional or general arteriolar or venous dilation
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
71 ug/kg/5M-C
TOXIC EFFECTS :
Behavioral - excitement Cardiac - arrhythmias (including changes in conduction) Cardiac - pulse rate increase, without fall in BP
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Human - infant
DOSE/DURATION :
1026 ug/kg
TOXIC EFFECTS :
Cardiac - pulse rate Vascular - BP lowering not characterized in autonomic section
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
200 ug/kg/15S-C
TOXIC EFFECTS :
Cardiac - cardiomyopathy including infarction Lungs, Thorax, or Respiration - dyspnea
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
256 ug/kg/1H-I
TOXIC EFFECTS :
Cardiac - arrhythmias (including changes in conduction)
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
108 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
60 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
107 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
16 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intramuscular
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
47 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
163 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
41 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
68 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
5795 ug/kg
TOXIC EFFECTS :
Sense Organs and Special Senses (Eye) - ptosis Gastrointestinal - hypermotility, diarrhea
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intramuscular
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
45 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
>400 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intramuscular
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
25 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - guinea pig
DOSE/DURATION :
140 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
128 mg/kg
SEX/DURATION :
male 28 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Paternal Effects - impotence
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
264 mg/kg
SEX/DURATION :
female 1-22 day(s) after conception lactating female 22 day(s) post-birth
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Specific Developmental Abnormalities - cardiovascular (circulatory) system Reproductive - Specific Developmental Abnormalities - blood and lymphatic systems (including spleen and marrow)

MUTATION DATA

TYPE OF TEST :
Cytogenetic analysis
TEST SYSTEM :
Human Lymphocyte
DOSE/DURATION :
30 umol/L
REFERENCE :
MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 244,135,1990 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X5040 No. of Facilities: 174 (estimated) No. of Industries: 1 No. of Occupations: 3 No. of Employees: 3974 (estimated) No. of Female Employees: 2638 (estimated)

 Safety Information

Symbol GHS06
GHS06
Signal Word Danger
Hazard Statements H301 + H311 + H331
Precautionary Statements P261-P280-P301 + P310-P311
Personal Protective Equipment Eyeshields;Faceshields;Gloves;type P2 (EN 143) respirator cartridges
Hazard Codes T: Toxic;
Risk Phrases R23/24/25
Safety Phrases S45-S36/37/39-S36/37
RIDADR UN 2811 6.1/PG 3
WGK Germany 3
RTECS YV8320000
Packaging Group III
Hazard Class 6.1(b)
HS Code 2926909090

 Customs

HS Code 2926909090
Summary HS:2926909090 other nitrile-function compounds VAT:17.0% Tax rebate rate:9.0% Supervision conditions:none MFN tariff:6.5% General tariff:30.0%

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 Synonyms

2-(3,4-Dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(1-methylethyl)pentanonitrilhydrochlorid
2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(1-methylethyl)pentanenitrile hydrochloride
MFCD00069355
Izoptin Hydrochloride
Benzeneacetonitrile, α-[3-[[2-(3,4-dimethoxyphenyl)ethyl]methylamino]propyl]-3,4-dimethoxy-α-(1-methylethyl)-, hydrochloride (1:1)
(±)-Verapamil hydrochloride
2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile hydrochloride (1:1)
Verogalid ER
2-(3,4-Dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-isopropylpentanenitrile hydrochloride
a-[3-[[2-(3,4-Dimethoxyphenyl)ethyl]methylamino]propyl]-3,4-dimethoxy-a-(1-methylethyl)benzeneacetonitrile Monohydrochloride
Verapamil Hydrochloride (Isoptin, Iproveratril, Calan)
Verapamil hydrochloride,α-[3-[[2-(3,4-Dimethoxyphenyl)ethyl]methylamino]propyl]-3,4-dimethoxy-α-(1-methylethyl)benzeneacetonitrilehydrochloride
5-[(3,4-dimethoxyphenethyl)(methyl)amino]-2-(3,4-dimethoxyphenyl)-2-isopropylpentanenitrile hydrochloride
4-cyano-4-(3,4-dimethoxyphenyl)-N-[2-(3,4-dimethoxyphenyl)ethyl]-N,5-dimethylhexan-1-aminium chloride
benzeneacetonitrile, a-[3-[[2-(3,4-dimethoxyphenyl)ethyl]methylamino]propyl]-3,4-dimethoxy-a-(1-methylethyl)-, hydrochloride (1:1)
benzeneacetonitrile, α-[3-[[2-(3,4-dimethoxyphenyl)ethyl]methylamino]propyl]-3,4-dimethoxy-α-(1-methylethyl)-, monohydrochloride
dl-Verapamil Hydrochloride
2-(3,4-diméthoxyphényl)-5-{[2-(3,4-diméthoxyphényl)éthyl](méthyl)amino}-2-(1-méthyléthyl)pentanenitrile chlorhydrate
2-(3,4-Dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-isopropylpentanenitrile hydrochloride (1:1)
Veraptin
Arpamyl
Veracim
Verapamil hydrochloride
(‘±)-Verapamil hydrochloride
Vasolan
Verexamil
Drosteakard
EINECS 205-800-5
Lekoptin Retard
UNII:V3888OEY5R
Verapamil (hydrochloride)
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