Verapamil

Modify Date: 2026-07-01 10:48:03

Verapamil structure	Common Name	Verapamil
	CAS Number	52-53-9	Molecular Weight	454.602
	Density	1.1±0.1 g/cm3	Boiling Point	586.2±50.0 °C at 760 mmHg
	Molecular Formula	C₂₇H₃₈N₂O₄	Melting Point	25°C
	MSDS	N/A	Flash Point	308.3±30.1 °C

Use of Verapamil

Verapamil ((±)-Verapamil) is a calcium channel blocker and a potent and orally active first-generation P-glycoprotein (P-gp) inhibitor. Verapamil also inhibits CYP3A4. Verapamil has the potential for high blood pressure, heart arrhythmias and angina treatment[1][2][3].

This table lists Chinese names, IUPAC names and various aliases of this chemical substance.

Name	2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile
Synonym	More Synonyms

This table contains bioactivity, target information and biological‑assay experimental data of this compound.

Description	Verapamil ((±)-Verapamil) is a calcium channel blocker and a potent and orally active first-generation P-glycoprotein (P-gp) inhibitor. Verapamil also inhibits CYP3A4. Verapamil has the potential for high blood pressure, heart arrhythmias and angina treatment[1][2][3].
Related Catalog	Signaling Pathways >> Membrane Transporter/Ion Channel >> Calcium Channel Signaling Pathways >> Metabolic Enzyme/Protease >> Cytochrome P450 Signaling Pathways >> Membrane Transporter/Ion Channel >> P-glycoprotein Research Areas >> Metabolic Disease
Target	Calcium channel[1] Permeability-glycoprotein (P-gp)[1] CYP3A4[1]
In Vitro	The EverFluor FL Verapamil (EFV) uptake by TR-iBRB2 cells is inhibited by cationic drugs, and inhibits by verapamil in a concentration-dependent manner with an IC50 of 98.0 μM[4].
In Vivo	Intravenous Verapamil is highly effective in the termination of paroxysmal reciprocating atrioventricular tachycardia, whether associated with preexcitation or involving the atrioventricular node alone[2]. Given orally it is useful for the prophylaxis of atrioventricular reentry tachycardia, and also in modulating the atrioventricular nodal response in atrial fibrillation[2].
References	[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 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.

This table shows physicochemical parameters including melting point, boiling point, density, solubility and optical rotation. Missing data is marked as N/A.

Density	1.1±0.1 g/cm3
Boiling Point	586.2±50.0 °C at 760 mmHg
Melting Point	25°C
Molecular Formula	C₂₇H₃₈N₂O₄
Molecular Weight	454.602
Flash Point	308.3±30.1 °C
Exact Mass	454.283173
PSA	63.95000
LogP	3.90
Vapour Pressure	0.0±1.6 mmHg at 25°C
Index of Refraction	1.526
InChIKey	SGTNSNPWRIOYBX-UHFFFAOYSA-N
SMILES	COc1ccc(CCN(C)CCCC(C#N)(c2ccc(OC)c(OC)c2)C(C)C)cc1OC

This table summarizes toxicological test data, acute & chronic toxicity and ecological hazard parameters for this chemical.

CHEMICAL IDENTIFICATION

RTECS NUMBER :: YV8300000

CHEMICAL NAME :: Valeronitrile, 5-((3,4-dimethoxyphenethyl)methylamino)-2-(3,4-dimeth oxyphenyl)-2-isopropy l-

CAS REGISTRY NUMBER :: 52-53-9

LAST UPDATED :: 199801

DATA ITEMS CITED :: 19

MOLECULAR FORMULA :: C27-H38-N2-O4

MOLECULAR WEIGHT :: 454.67

WISWESSER LINE NOTATION :: 1OR BO1 DXCN&Y1&1&3N1&2R CO1 DO1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

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 :: 2 gm/kg

TOXIC EFFECTS :: Sense Organs and Special Senses (Olfaction) - effect, not otherwise specified Cardiac - other changes Vascular - BP lowering not characterized in autonomic section

REFERENCE :: CHETBF Chest. (American College of Chest Physicians, 911 Busse Hwy, Park Ridge, IL 60068) V.57- 1970- Volume(issue)/page/year: 75,200,1979

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - woman

DOSE/DURATION :: 64 mg/kg

TOXIC EFFECTS :: Cardiac - pulse rate Cardiac - change in rate Vascular - BP lowering not characterized in autonomic section

REFERENCE :: BMJOAE British Medical Journal. (British Medical Assoc., BMA House, Tavistock Sq., London WC1H 9JR, UK) V.1- 1857- Volume(issue)/page/year: 2,1127,1978

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - man

DOSE/DURATION :: 48 mg/kg/2W-I

TOXIC EFFECTS :: Liver - hepatitis (hepatocellular necrosis), diffuse

REFERENCE :: NEJMAG New England Journal of Medicine. (Massachusetts Medical Soc., 10 Shattuck St., Boston, MA 02115) V.198- 1928- Volume(issue)/page/year: 306,612,1982

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 :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - man

DOSE/DURATION :: 3429 ug/kg

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold Cardiac - pulse rate Lungs, Thorax, or Respiration - acute pulmonary edema

REFERENCE :: CCMDC7 Critical Care Medicine. (Williams & Wilkins, 428 E. Preston Street, Baltimore, MD 21202) V.1- 1973- Volume(issue)/page/year: 19,436,1991

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Human - man

DOSE/DURATION :: 1429 ug/kg/5M-C

TOXIC EFFECTS :: Cardiac - pulse rate Lungs, Thorax, or Respiration - cyanosis Skin and Appendages - sweating

REFERENCE :: NEJMAG New England Journal of Medicine. (Massachusetts Medical Soc., 10 Shattuck St., Boston, MA 02115) V.198- 1928- Volume(issue)/page/year: 306,238,1982

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Human - man

DOSE/DURATION :: 71 ug/kg

TOXIC EFFECTS :: Cardiac - pulse rate increase, without fall in BP Lungs, Thorax, or Respiration - dyspnea

REFERENCE :: AHJOA2 American Heart Journal. (C.V. Mosby Co., 11830 Westline Industrial Dr., St. Louis, MO 63146) V.1- 1925- Volume(issue)/page/year: 111,622,1986

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Human - child

DOSE/DURATION :: 250 ug/kg/5M-C

TOXIC EFFECTS :: Cardiac - arrhythmias (including changes in conduction)

REFERENCE :: AHJOA2 American Heart Journal. (C.V. Mosby Co., 11830 Westline Industrial Dr., St. Louis, MO 63146) V.1- 1925- Volume(issue)/page/year: 106,145,1983

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 163 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: EJMCA5 European Journal of Medicinal Chemistry--Chimie Therapeutique. (Editions Scientifiques Elsevier, 29 rue Buffon, F-75005, Paris, France) V.9- 1974- Volume(issue)/page/year: 25,351,1990

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 7250 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: PCJOAU Pharmaceutical Chemistry Journal (English Translation). Translation of KHFZAN. (Plenum Pub. Corp., 233 Spring St., New York, NY 10013) No.1- 1967- Volume(issue)/page/year: 22,123,1988

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 130 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: FATOAO Farmakologiya i Toksikologiya (Moscow). For English translation, see PHTXA6 and RPTOAN. (V/O Mezhdunarodnaya Kniga, 113095 Moscow, USSR) V.2- 1939- Volume(issue)/page/year: 54(2),40,1991

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 43 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JDGRAX Journal of Drug Research. (National Organization for Drug Research and Control, POB 29, Cairo, Egypt) V.2- 1969- Volume(issue)/page/year: 15(1-2),121,1984

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 30770 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JPPMAB Journal of Pharmacy and Pharmacology. (Pharmaceutical Soc. of Great Britain, 1 Lambeth High St., London SEI 7JN, UK) V.1- 1949- Volume(issue)/page/year: 34,329,1982

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.7-9, 1974-76. For publisher information, see TOERD9. Volume(issue)/page/year: 8,188,1975 ** REPRODUCTIVE DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

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

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

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 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X4662 No. of Facilities: 65 (estimated) No. of Industries: 1 No. of Occupations: 2 No. of Employees: 14268 (estimated) No. of Female Employees: 7372 (estimated)

This table covers safety warnings, protective measures, incompatible substances and disposal guidelines for this compound.

Hazard Codes	C
Risk Phrases	R14:Reacts violently with water. R34:Causes burns. R37:Irritating to the respiratory system.
Safety Phrases	S26-S36/37/39-S43-S45
RIDADR	UN 1939 8/PG 2
WGK Germany	3
Packaging Group	II
Hazard Class	8

This table presents publicly reported synthetic routes, reaction conditions, reactants and product information of the compound.

2-(3,4-dimethox...

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Literature: Wu, Lingyun; Hartwig, John F. Journal of the American Chemical Society, 2005 , vol. 127, # 45 p. 15824 - 15832

3-Methylbutanen...

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Literature: Wu, Lingyun; Hartwig, John F. Journal of the American Chemical Society, 2005 , vol. 127, # 45 p. 15824 - 15832

2-(2-[1,3]dioxo...

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Literature: Wu, Lingyun; Hartwig, John F. Journal of the American Chemical Society, 2005 , vol. 127, # 45 p. 15824 - 15832

This table lists upstream starting materials and downstream derivative products related to this chemical.

Precursor 4
CAS#:871703-17-2 2-(3,4-dimethox... CAS#:3490-06-0 N-Methylhomover... CAS#:625-28-5 3-Methylbutanen... CAS#:128776-24-9 2-(2-[1,3]dioxo...
DownStream 6
CAS#:27487-66-7 5-Amino-2-(3,4-... CAS#:34245-14-2 rac D 617 (Vera... CAS#:67018-85-3 Norverapamil CAS#:71539-08-7 pr 25
CAS#:38321-02-7 dexverapamil CAS#:36622-29-4 (S)-(-)-Verapam...

This table collects all English aliases, systematic names and CAS‑related synonyms of the compound.

eronitrile

aleronitrile

2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile

EINECS 200-145-1

5-[(3,4-Dimethoxyphenethyl)methylamino]-2-(3,4-dimethoxyphenyl)-2-isopropylvaleronitrile

R,S-Verapamil

a-((N-Methyl-N-homoveratryl)-g-aminopropyl)-3,4-dimethoxyphenylacetonitrile

Dilacoran

VPL

Vasolan

a-Isopropyl-a-[(N-methyl-N-homoveratryl)-g-aminopropyl]-3,4-dimethoxyphenylacetonitrile

Verapamil

2-isopropyl

MFCD00056240

(±)-Verapamil

D-365

CP 16533-1

2-(3,4-Dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-isopropylpentanenitrile

dl-Verapamil

a-[3-[[2-(3,4-Dimethoxyphenyl)ethyl]methylamino]propyl]-3,4-dimethoxy-a-(1-methylethyl)benzeneacetonitrile

This section contains frequently‑asked‑questions about this compound, including basic parameters, properties, storage conditions and corresponding answers.

Q: What is the English name of 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile?

A: The English name of 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile is 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile.

Q: What is the polar surface area (PSA) of 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile?

A: Polar surface area (PSA) of 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile is 63.95000.

Q: What is the molecular weight of 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile?

A: Molecular weight of 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile is 454.602.

Q: What are the downstream products of 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile?

A: Related downstream products(CAS) of 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile: 27487-66-7;34245-14-2;67018-85-3;71539-08-7;38321-02-7;36622-29-4.

Q: What is the SMILES notation of 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile?

A: SMILES notation of 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile is COc1ccc(CCN(C)CCCC(C#N)(c2ccc(OC)c(OC)c2)C(C)C)cc1OC.

Q: What are the uses of 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile?

A: Main uses of 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile: Verapamil ((±)-Verapamil) is a calcium channel blocker and a potent and orally active first-generation P-glycoprotein (P-gp) inhibitor. Verapamil also inhibits CYP3A4. Verapamil has the potential for high blood pressure, heart arrhythmias and angina treatment[1][2][3].

Q: What is the melting point of 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile?

A: Melting point of 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile is 25°C.

Q: What is the CAS number of 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile?

A: CAS number of 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile is 52-53-9.

Q: What is the safety information for 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile?

A: Safety information for 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile: S26-S36/37/39-S43-S45.

Q: What is the boiling point of 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile?

A: Boiling point of 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile is 586.2±50.0 °C at 760 mmHg.

This table lists manufacturers and suppliers of this compound, including vendor names and product supply reference information.

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