CAS 152-11-4|Verapamil HCl

Introduction：Basic information about CAS 152-11-4|Verapamil HCl, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. Verapamil HCl BiologicalActivity
3. Chemical & Physical Properties
4. Toxicological Information
CHEMICAL IDENTIFICATION
HEALTH HAZARD DATA
ACUTE TOXICITY DATA
MUTATION DATA
5. Safety Information
6. Customs
7. Articles96
8. Synonyms

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	ChineseUSA	Flash Point	308.3ºC
Symbol	GHS06	Signal Word	Danger

Names

Name	(±)-Verapamil hydrochloride
Synonym	More Synonyms

Verapamil HCl BiologicalActivity

Description	Verapamil hydrochloride is a calcium channel antagonist.
Related Catalog	Signaling Pathways >>Membrane Transporter/Ion Channel >>Calcium ChannelResearch Areas >>Cardiovascular Disease
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
InChIKey	DOQPXTMNIUCOSY-UHFFFAOYSA-N
SMILES	COc1ccc(CCN(C)CCCC(C#N)(c2ccc(OC)c(OC)c2)C(C)C)cc1OC.Cl
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
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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