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Substance Name: Verapamil [USAN:INN:BAN]
RN: 52-53-9
UNII: CJ0O37KU29
InChIKey: SGTNSNPWRIOYBX-UHFFFAOYSA-N

Note

  • A calcium channel blocker that is a class IV anti-arrhythmia agent.

Molecular Formula

  • C27-H38-N2-O4

Molecular Weight

  • 454.607
 

Classification Codes

  • Anti-Arrhythmia Agents
  • Calcium Channel Blockers
  • Cardiovascular Agents
  • Drug / Therapeutic Agent
  • Human Data
  • Membrane Transport Modulators
  • Reproductive Effect
  • Vasodilator (Coronary)
  • Vasodilator Agents

Names and Synonyms

Name of Substance

  • Verapamil
  • Verapamil [USAN:INN:BAN]

MeSH Heading

  • Verapamil

Synonyms

  • 5-((3,4-Dimethoxyphenethyl)methylamino)-2-(3,4-dimethoxyphenyl)-2-isopropylvaleronitrile
  • alpha-((N-Methyl-N-homoveratryl)-gamma-aminopropyl)-3,4-dimethoxyphenylacetonitrile
  • alpha-(3-((2-(3,4-Dimethoxyphenyl)ethyl)-methylamino)propyl)-3,4-dimethoxy-alpha-(1-methylethyl)benzeneacetonitrile
  • alpha-Isopropyl-alpha-((N-methyl-N-homoveratryl)-gamma-aminopropyl)-3,4-dimethoxyphenylacetonitrile
  • Benzeneacetonitrile, alpha-(3-((2-(3,4-dimethoxyphenyl)ethyl)methylamino) propyl)-3,4-dimethoxy-alpha-(1-methylethyl)-
  • Benzeneacetonitrile, alpha-(3-((2-(3,4-dimethoxyphenyl)ethyl)methylamino)propyl)-3,4-dimethoxy-alpha-(1-methylethyl)-
  • CCRIS 6749
  • CP 16533-1
  • CP-16,533-1
  • CP-16533-1
  • D 365
  • D-365
  • Dexverapamil
  • Dilacoran
  • dl-Verapamil
  • EINECS 200-145-1
  • EINECS 260-462-6
  • Falicard
  • Finoptin
  • HSDB 3928
  • Iproveratril
  • Isoptimo
  • Isoptine
  • Lekoptin
  • NSC 135784
  • NSC 272306NA
  • R,S-Verapamil
  • UNII-CJ0O37KU29
  • Valeronitrile, 5-((3,4-dimethoxyphenethyl)methylamino)-2-(3,4-dimethoxyphenyl)-2-isopropyl-
  • Vasolan
  • Verapamil
  • Verapamilo
  • Verapamilo [INN-Spanish]
  • Verapamilum
  • Verapamilum [INN-Latin]

Systematic Names

  • Benzeneacetonitrile, alpha-(3-((2-(3,4-dimethoxyphenyl)ethyl)methylamino)propyl)-3,4-dimethoxy-alpha-(1-methylethyl)-
  • Valeronitrile, 5-((3,4-dimethoxyphenethyl)methylamino)-2-(3,4-dimethoxyphenyl)-2-isopropyl-
  • Verapamil

Registry Numbers

CAS Registry Number

  • 52-53-9

FDA UNII

  • CJ0O37KU29

Other Registry Numbers

  • 1007128-78-0
  • 56949-77-0
  • 7482-85-1

System Generated Number

  • 0000052539

Structure Descriptors

InChI

1S/C27H38N2O4/c1-20(2)27(19-28,22-10-12-24(31-5)26(18-22)33-7)14-8-15-29(3)16-13-21-9-11-23(30-4)25(17-21)32-6/h9-12,17-18,20H,8,13-16H2,1-7H3

InChIKey

SGTNSNPWRIOYBX-UHFFFAOYSA-N

Smiles

c1([C@@](CCC[N@@](CCc2cc(c(OC)cc2)OC)C)(C(C)C)C#N)cc(c(OC)cc1)OC

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
child TDLo intravenous 250ug/kg/5M-C (0.25mg/kg) CARDIAC: ARRHYTHMIAS (INCLUDING CHANGES IN CONDUCTION) American Heart Journal. Vol. 106, Pg. 145, 1983.
man LDLo oral 83mg/kg (83mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

CARDIAC: CARDIOMYOPATHY INCLUDING INFARCTION

VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION
American Journal of Emergency Medicine. Vol. 7, Pg. 624, 1989.
man LDLo oral 2gm/kg (2000mg/kg) VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION

SENSE ORGANS AND SPECIAL SENSES: OTHER CHANGES: OLFACTION

CARDIAC: OTHER CHANGES
Chest. Vol. 75, Pg. 200, 1979.
man TDLo intravenous 71ug/kg (0.071mg/kg) CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
American Heart Journal. Vol. 111, Pg. 622, 1986.
man TDLo intravenous 1429ug/kg/5M- (1.429mg/kg) LUNGS, THORAX, OR RESPIRATION: CYANOSIS

CARDIAC: PULSE RATE

SKIN AND APPENDAGES (SKIN): SWEATING: OTHER
New England Journal of Medicine. Vol. 306, Pg. 238, 1982.
man TDLo oral 3429ug/kg (3.429mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

CARDIAC: PULSE RATE

LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA
Critical Care Medicine. Vol. 19, Pg. 436, 1991.
man TDLo oral 42857ug/kg (42.857mg/kg) VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION

CARDIAC: EKG CHANGES NOT DIAGNOSTIC OF ABOVE
European Heart Journal. Vol. 2, Pg. 239, 1981.
man TDLo oral 46mg/kg (46mg/kg) CARDIAC: EKG CHANGES NOT DIAGNOSTIC OF ABOVE

SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE

VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION
Clinical Toxicology. Vol. 17, Pg. 395, 1980.
man TDLo oral 48mg/kg/2W-I (48mg/kg) LIVER: "HEPATITIS (HEPATOCELLULAR NECROSIS), DIFFUSE" New England Journal of Medicine. Vol. 306, Pg. 612, 1982.
mouse LD50 intraperitoneal 43mg/kg (43mg/kg)   Journal of Drug Research. Vol. 15(1-2), Pg. 121, 1984.
mouse LD50 intravenous 1520ug/kg (1.52mg/kg)   European Journal of Toxicology and Environmental Hygiene. Vol. 8, Pg. 188, 1975.
mouse LD50 oral 130mg/kg (130mg/kg)   Farmakologiya i Toksikologiya Vol. 54(2), Pg. 40, 1991.
mouse LD50 subcutaneous 30770ug/kg (30.77mg/kg)   Journal of Pharmacy and Pharmacology. Vol. 34, Pg. 329, 1982.
rat LD50 intravenous 7250ug/kg (7.25mg/kg)   Pharmaceutical Chemistry Journal Vol. 22, Pg. 123, 1988.
rat LD50 oral 163mg/kg (163mg/kg)   European Journal of Medicinal Chemistry--Chimie Therapeutique. Vol. 25, Pg. 351, 1990.
women LDLo oral 1364ug/kg (1.364mg/kg) LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA

CARDIAC: OTHER CHANGES

LIVER: FATTY LIVER DEGERATION
Archives of Toxicology. Vol. 37, Pg. 89, 1977.
women LDLo oral 192mg/kg (192mg/kg) BEHAVIORAL: COMA

CARDIAC: PULSE RATE

VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION
Netherlands Journal of Medicine. Vol. 26, Pg. 130, 1983.
women LDLo oral 300mg/kg (300mg/kg) CARDIAC: EKG CHANGES NOT DIAGNOSTIC OF ABOVE

CARDIAC: PULSE RATE

VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION
Medical Journal of Australia. Vol. 158, Pg. 202, 1993.
women TDLo oral 48mg/kg (48mg/kg) CARDIAC: EKG CHANGES NOT DIAGNOSTIC OF ABOVE

VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
Clinical Cardiology. Vol. 5, Pg. 219, 1982.
women TDLo oral 64mg/kg (64mg/kg) VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION

CARDIAC: CHANGE IN RATE

CARDIAC: PULSE RATE
British Medical Journal. Vol. 2, Pg. 1127, 1978.
women TDLo oral 80mg/kg (80mg/kg) VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION

BEHAVIORAL: COMA

CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP
Human & Experimental Toxicology. Vol. 16, Pg. 35, 1997.
women TDLo oral 128mg/kg (128mg/kg) CARDIAC: ARRHYTHMIAS (INCLUDING CHANGES IN CONDUCTION)

BEHAVIORAL: GENERAL ANESTHETIC

KIDNEY, URETER, AND BLADDER: URINE VOLUME DECREASED
International Journal of Cardiology. Vol. 1, Pg. 101, 1981.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point < 25 deg C   EXP
pKa Dissociation Constant 8.92 (none)   EXP
log P (octanol-water) 3.79 (none)   EXP
Water Solubility 4.470 mg/L 25 EST
Vapor Pressure 2.79E-11 mm Hg 25 EST
Henry's Law Constant 8.79E-15 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 1.86E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.