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Substance Name: Mepivacaine [INN:BAN]
RN: 96-88-8
UNII: B6E06QE59J
InChIKey: INWLQCZOYSRPNW-UHFFFAOYSA-N

Note

  • A local anesthetic that is chemically related to BUPIVACAINE but pharmacologically related to LIDOCAINE. It is indicated for infiltration, nerve block, and epidural anesthesia. Mepivacaine is effective topically only in large doses and therefore should not be used by this route. (From AMA Drug Evaluations, 1994, p168)

Molecular Formula

  • C15-H22-N2-O

Molecular Weight

  • 246.3518
 

Classification Codes

  • Anesthetics
  • Anesthetics, Local
  • Central Nervous System Agents
  • Central Nervous System Depressants
  • Drug / Therapeutic Agent
  • Peripheral Nervous System Agents
  • Reproductive Effect
  • Sensory System Agents

Names and Synonyms

Name of Substance

  • Mepivacaine
  • Mepivacaine [INN:BAN]

MeSH Heading

  • Mepivacaine

Synonyms

  • (+-)-1-Methyl-2',6'-pipecoloxylidide
  • 5-22-01-00223 (Beilstein Handbook Reference)
  • BRN 0211230
  • EINECS 202-543-0
  • Isocaine
  • Mepihexal
  • Mepivacaina
  • Mepivacaina [INN-Spanish]
  • Mepivacaine
  • Mepivacainum
  • Mepivacainum [INN-Latin]
  • N-Methyl-2-pipecolic acid, 2,6-dimethylanilide
  • N-Methyl-2-pipecolic acid, 2,6-xylidide
  • N-Methylhexahydro-2-picolinic acid, 2,6-dimethylanilide
  • Scandicain
  • Scandicaine
  • UNII-B6E06QE59J

Systematic Names

  • 2',6'-Pipecoloxylidide, 1-methyl-
  • 2-Piperidinecarboxamide, N-(2,6-dimethylphenyl)-1-methyl-
  • N-(2,6-Dimethylphenyl)-1-methylpiperidine-2-carboxamide

Registry Numbers

CAS Registry Number

  • 96-88-8

FDA UNII

  • B6E06QE59J

Other Registry Number

  • 22801-44-1

Related Registry Number

  • 1722-62-9 (mono-hydrochloride)

System Generated Number

  • 0000096888

Structure Descriptors

InChI

1S/C15H22N2O/c1-11-7-6-8-12(2)14(11)16-15(18)13-9-4-5-10-17(13)3/h6-8,13H,4-5,9-10H2,1-3H3,(H,16,18)

InChIKey

INWLQCZOYSRPNW-UHFFFAOYSA-N

Smiles

Cc1cccc(c1NC(=O)C2CCCCN2C)C

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intravenous 35mg/kg (35mg/kg)   Acta Pharmacologica et Toxicologica. Vol. 31, Pg. 273, 1972.
mouse LD50 oral > 5gm/kg (5000mg/kg)   Drugs in Japan Vol. 6, Pg. 845, 1982.
mouse LD50 subcutaneous 270mg/kg (270mg/kg)   Acta Anaesthesiologica Scandinavica. Vol. 9, Pg. 1, 1965.
mouse LDLo intraperitoneal 135mg/kg (135mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: TREMOR
Toho Igakkai Zasshi. Journal of Medical Society of Toho University. Vol. 9, Pg. 38, 1962.
rabbit LDLo intravenous 53mg/kg (53mg/kg)   Acta Pharmacologica et Toxicologica. Vol. 31, Pg. 273, 1972.
rat LD50 intravenous 30mg/kg (30mg/kg)   Annual Review of Pharmacology. Vol. 9, Pg. 503, 1969.
rat LD50 oral > 5gm/kg (5000mg/kg)   Drugs in Japan Vol. 6, Pg. 845, 1982.
rat LD50 subcutaneous 500mg/kg (500mg/kg)   Acta Pharmacologica et Toxicologica. Vol. 31, Pg. 273, 1972.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 150.5 deg C   EXP
pKa Dissociation Constant 7.7 (none)   EXP
log P (octanol-water) 1.95 (none)   EXP
Water Solubility 7000 mg/L 23 EXP
Vapor Pressure 2.18E-07 mm Hg 25 EST
Henry's Law Constant 7.67E-11 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 1.21E-10 cm3/molecule-sec 25 EST

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