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Substance Name: Dibucaine hydrochloride [USP:JAN]
RN: 61-12-1
UNII: Z97702A5DG
InChIKey: IVHBBMHQKZBJEU-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.Cl-H

Molecular Weight

  • 379.929
 

Classification Codes

  • Anesthetic (Local)
  • Drug / Therapeutic Agent
  • Mutation Data
  • Skin / Eye Irritant
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Names and Synonyms

Name of Substance

  • Dibucaine hydrochloride [USP:JAN]

Synonyms

  • 2-Butoxy-N-(2-(diethylamino)ethyl)cinchoninamide monohydrochloride
  • 2-Butoxy-N-(2-diethylaminoethyl)cinchoninamide hydrochloride
  • 2-Butoxy-N-(2-diethylaminoethyl)cinchoninic acid amide hydrochloride
  • 2-N-Butoxy-N-(2-diethylaminoethyl)cinchoninamide hydrochloride
  • 4-Quinolinecarboxamide, 2-butoxy-N-(2-(diethylamino)ethyl)-, monohydrochloride
  • Benzolin (local anesthetic)
  • Butoxycinchoninic acid diethylethylenediamide hydrochloride
  • C 3225
  • Cincaine chloride
  • Cincaine hydrochloride
  • Cinchocaine hydrochloride
  • Cinchocainium chloride
  • Cinchokain hydrochlorid
  • Cinchokain hydrochlorid [Czech]
  • Dibucaine HCl
  • Dibucaine hydrochloride
  • EINECS 200-498-1
  • Heavy Solution Nupercaine
  • Nupercainal
  • Nupercaine
  • Nupercaine hydrochloride
  • Percain
  • Percaine
  • Percamin S
  • Sovcain
  • Sovcaine
  • Sovcainum
  • UNII-Z97702A5DG

Systematic Names

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

Registry Numbers

CAS Registry Number

  • 61-12-1

FDA UNII

  • Z97702A5DG

System Generated Number

  • 0000061121

Molecular Formulas

Molecular Formula

  • C20-H29-N3-O2.Cl-H

Molecular Formula Fragments

  • C20-H29-N3-O2
  • Cl-H
  • COMPONENT

Structure Descriptors

InChI

1S/C20H29N3O2.ClH/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);1H

InChIKey

IVHBBMHQKZBJEU-UHFFFAOYSA-N

Smiles

CCCCOc1cc(c2ccccc2n1)C(=O)NCCN(CC)CC.Cl

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
bird - wild LD50 oral 42mg/kg (42mg/kg)   Toxicology and Applied Pharmacology. Vol. 21, Pg. 315, 1972.
frog LDLo parenteral 55mg/kg (55mg/kg) CARDIAC: OTHER CHANGES

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

PERIPHERAL NERVE AND SENSATION: SPASTIC PARALYSIS WITH OR WITHOUT SENSORY CHANGE
Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 166, Pg. 437, 1932.
guinea pig LD50 intravenous 3097ug/kg (3.097mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 93, Pg. 388, 1948.
guinea pig LD50 subcutaneous 15300ug/kg (15.3mg/kg)   Quarterly Journal of Pharmacy & Pharmacology. Vol. 20, Pg. 380, 1947.
mouse LD50 intraperitoneal 29mg/kg (29mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 94, Pg. 299, 1948.
mouse LD50 intravenous 3800ug/kg (3.8mg/kg)   European Journal of Pharmacology. Vol. 3, Pg. 58, 1968.
mouse LD50 subcutaneous 25400ug/kg (25.4mg/kg)   Proceedings of the Society for Experimental Biology and Medicine. Vol. 103, Pg. 353, 1960.
rabbit LD50 intravenous 2mg/kg (2mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 103, Pg. 306, 1951.
rabbit LD50 subcutaneous 7743ug/kg (7.743mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 93, Pg. 388, 1948.
rabbit LD50 unreported 5mg/kg (5mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 24, Pg. 1957, 1974.
rabbit LDLo intraspinal 2mg/kg (2mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 57, Pg. 221, 1936.
rat LD50 intraperitoneal 22mg/kg (22mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 8, Pg. 708, 1958.
rat LD50 intravenous 52mg/kg (52mg/kg)   Drugs in Japan Vol. -, Pg. 478, 1990.
rat LD50 subcutaneous 27mg/kg (27mg/kg)   Drugs in Japan Vol. -, Pg. 478, 1990.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 94 dec deg C   EXP
log P (octanol-water) 2.520 (none)   EST
Atmospheric OH Rate Constant 7.85E-11 cm3/molecule-sec 25 EST

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