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Substance Name: Dibucaine [USP]
RN: 85-79-0
UNII: L6JW2TJG99
InChIKey: PUFQVTATUTYEAL-UHFFFAOYSA-N

Note

  • A local anesthetic of the amide type now generally used for surface anesthesia. It is one of the most potent and toxic of the long-acting local anesthetics and its parenteral use is restricted to spinal anesthesia. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1006)

Molecular Formula

  • C20-H29-N3-O2

Molecular Weight

  • 343.4681
 

Classification Codes

  • Anesthetic (Local)
  • Anesthetics
  • Anesthetics, Local
  • Central Nervous System Agents
  • Central Nervous System Depressants
  • Drug / Therapeutic Agent
  • Human Data
  • Peripheral Nervous System Agents
  • Sensory System Agents
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Names and Synonyms

Name of Substance

  • Cinchocaine [INN]
  • Dibucaine
  • Dibucaine [USP]

MeSH Heading

  • Dibucaine

Synonyms

  • 2-Butoxy-N-(2-(diethylamino)ethyl)cinchoninamide
  • 2-Butoxy-N-(beta-diethylaminoethyl)cinchoninamide
  • 2-Butoxyquinoline-4-carboxylic acid diethylaminoethylamide
  • 2-N-Butoxy-N-(2-diethylaminoethyl)cinchoninamide
  • 4-22-00-02284 (Beilstein Handbook Reference)
  • 4-Quinolinecarboxamide, 2-butoxy-N-(2-(diethylamino)ethyl)-
  • alpha-Butyloxycinchonic acid-gamma-diethylethylenediamine
  • alpha-Butyloxycinchoninic acid diethylethylenediamide
  • BRN 0275489
  • Cincainum
  • Cinchocaine
  • Cinchocainum
  • Cinchocainum [INN-Latin]
  • Cinchoninamide, 2-butoxy-N-(2-(diethylamino)ethyl)-
  • Cincocaina
  • Cincocaina [DCIT]
  • Cincocainio
  • Cincocainio [INN-Spanish]
  • Dermacaine
  • Dibucain
  • Dibucaine
  • Dibucaine Base
  • Dibucainum
  • EINECS 201-632-1
  • HSDB 3312
  • N-(2-(Diethylamino)ethyl)-2-butoxycinchoninamide
  • NSC 159055
  • Nupercainal
  • Nupercainal (VAN)
  • Nupercaine
  • Percamine
  • Sovcaine
  • UNII-L6JW2TJG99

Systematic Names

  • 4-Quinolinecarboxamide, 2-butoxy-N-(2-(diethylamino)ethyl)-
  • Cinchocaine
  • Cinchoninamide, 2-butoxy-N-(2-(diethylamino)ethyl)-

Registry Numbers

CAS Registry Number

  • 85-79-0

FDA UNII

  • L6JW2TJG99

System Generated Number

  • 0000085790

Structure Descriptors

InChI

1S/C20H29N3O2/c1-4-7-14-25-19-15-17(16-10-8-9-11-18(16)22-19)20(24)21-12-13-23(5-2)6-3/h8-11,15H,4-7,12-14H2,1-3H3,(H,21,24)

InChIKey

PUFQVTATUTYEAL-UHFFFAOYSA-N

Smiles

c12c(cc(nc1cccc2)OCCCC)C(=O)NCCN(CC)CC

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
child LDLo oral 50mg/kg (50mg/kg)   "Toxicology of Drugs and Chemicals," Deichmann, W.B., New York, Academic Press, Inc., 1969Vol. -, Pg. 209, 1969.
frog LDLo intraspinal 4mg/kg (4mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 45, Pg. 291, 1932.
guinea pig LDLo subcutaneous 112mg/kg (112mg/kg)   Physiological Reviews. Vol. 12, Pg. 190, 1932.
mouse LD50 intraperitoneal 24500ug/kg (24.5mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 10, Pg. 925, 1960.
mouse LD50 subcutaneous 28500ug/kg (28.5mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 10, Pg. 925, 1960.
mouse LDLo intravenous 6mg/kg (6mg/kg)   Journal of the American Pharmaceutical Association, Scientific Edition. Vol. 39, Pg. 4, 1950.
rabbit LD50 intravenous 2500ug/kg (2.5mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD Proceedings of the Society for Experimental Biology and Medicine. Vol. 29, Pg. 368, 1932.
rabbit LD50 subcutaneous 8500ug/kg (8.5mg/kg) BEHAVIORAL: EXCITEMENT

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Proceedings of the Society for Experimental Biology and Medicine. Vol. 29, Pg. 368, 1932.
rabbit LDLo intraspinal 2100ug/kg (2.1mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 54, Pg. 137, 1935.
rat LDLo intraperitoneal 7mg/kg (7mg/kg)   Toxicology and Applied Pharmacology. Vol. 1, Pg. 156, 1959.

Physical Properties

Physical Property Value Units Temp (deg C) Source
pKa Dissociation Constant 8.85 (none)   EXP
log P (octanol-water) 4.4 (none)   EXP
Water Solubility 42 mg/L 21 EXP
Vapor Pressure 1.36E-10 mm Hg 25 EST
Henry's Law Constant 9.10E-16 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 1.45E-10 cm3/molecule-sec 25 EST

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