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Substance Name: Ketamine hydrochloride [USAN:USP:JAN]
RN: 1867-66-9
UNII: O18YUO0I83
InChIKey: VCMGMSHEPQENPE-UHFFFAOYSA-N

Note

  • A cyclohexanone derivative used for induction of anesthesia. Its mechanism of action is not well understood, but ketamine can block NMDA receptors (RECEPTORS, N-METHYL-D-ASPARTATE) and may interact with sigma receptors.

Molecular Formula

  • C13-H16-Cl-N-O.Cl-H

Molecular Weight

  • 274.1893
 

Classification Codes

Classification Codes

  • Anesthetic
  • Drug / Therapeutic Agent
  • Human Data
  • Mutation Data
  • Reproductive Effect

Superlist Classification Code

  • DEA Schedule III
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Names and Synonyms

Name of Substance

  • Ketamine hydrochloride [USAN:USP:JAN]

Synonyms

  • (+-)-2-(o-Chlorophenyl)-2-(methylamino)cyclohexanone hydrochloride
  • (+-)-Ketamine hydrochloride
  • Calipsol
  • CI 581
  • CI-581
  • CL 369
  • CN-52,372-2
  • Cyclohexanone, 2-(2-chlorophenyl)-2-(methylamino)-, hydrochloride, (+-)-
  • EC 217-484-6
  • EINECS 217-484-6
  • Kalipsol
  • Ketalar
  • Ketamine chloride
  • Ketamine HCl
  • Ketamine hydrochloride
  • Ketanest
  • Ketaset
  • Ketavet
  • Ketavet (Veterinary)
  • Ketavet 100
  • Ketolar
  • PMI-150
  • UNII-O18YUO0I83
  • Vetalar

Systematic Names

  • Cyclohexanone, 2-(2-chlorophenyl)-2-(methylamino)-, hydrochloride
  • Cyclohexanone, 2-(o-chlorophenyl)-2-(methylamino)-, hydrochloride, (+-)-
  • Ketamine hydrochloride

Superlist Names

  • DEA No. 7285
  • Ketaset

Mixture Name

  • Ketaset Plus (Veterinary)

Registry Numbers

CAS Registry Number

  • 1867-66-9

FDA UNII

  • O18YUO0I83

Other Registry Numbers

  • 100477-73-4
  • 42551-62-2
  • 79499-52-8
  • 81771-21-3
  • 96448-41-8

System Generated Number

  • 0001867669

Molecular Formulas

Molecular Formula

  • C13-H16-Cl-N-O.Cl-H

Molecular Formula Fragments

  • C13-H16-Cl-N-O
  • Cl-H
  • COMPONENT

Structure Descriptors

InChI

1S/C13H16ClNO.ClH/c1-15-13(9-5-4-8-12(13)16)10-6-2-3-7-11(10)14;/h2-3,6-7,15H,4-5,8-9H2,1H3;1H

InChIKey

VCMGMSHEPQENPE-UHFFFAOYSA-N

Smiles

Cl.CNC1(CCCCC1=O)c2ccccc2Cl

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
chicken LD50 intravenous 67900ug/kg (67.9mg/kg) BEHAVIORAL: GENERAL ANESTHETIC

BEHAVIORAL: TREMOR

BEHAVIORAL: SLEEP
American Journal of Veterinary Research. Vol. 45, Pg. 531, 1984.
child TDLo intramuscular 4mg/kg (4mg/kg) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES Annals of Emergency Medicine. Vol. 22, Pg. 613, 1993.
child TDLo intramuscular 4mg/kg (4mg/kg) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP
American Journal of Emergency Medicine. Vol. 14, Pg. 580, 1996.
child TDLo intravenous 13200ug/kg (13.2mg/kg) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION Annals of Emergency Medicine. Vol. 34, Pg. 492, 1999.
guinea pig LD50 intramuscular 361mg/kg (361mg/kg)   Veterinary and Human Toxicology. Vol. 24, Pg. 410, 1982.
human TDLo intravenous 2mg/kg (2mg/kg) BEHAVIORAL: ANALGESIA British Medical Journal. Vol. 2, Pg. 943, 1976.
infant TDLo multiple routes 11587ug/kg (11.587mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA British Journal of Anesthesia. Vol. 58, Pg. 573, 1986.
man LDLo oral 13333ug/kg (13.333mg/kg) LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA Journal of Forensic Sciences. Vol. 39, Pg. 1314, 1994.
man TDLo unreported 1mg/kg (1mg/kg) BEHAVIORAL: ANALGESIA

BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"

BEHAVIORAL: COMA
U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#03551,
mouse LD50 intramuscular 356mg/kg (356mg/kg)   Zhongguo Yaolixue Yu Dulixue Zazhi. Vol. 9, Pg. 96, 1995.
mouse LD50 intraperitoneal 224mg/kg (224mg/kg)   Drugs in Japan Vol. 6, Pg. 264, 1982.
mouse LD50 intravenous 55900ug/kg (55.9mg/kg)   Drugs in Japan Vol. 6, Pg. 264, 1982.
mouse LD50 oral 617mg/kg (617mg/kg)   Drugs in Japan Vol. 6, Pg. 264, 1982.
rat LD50 intraperitoneal 224mg/kg (224mg/kg)   Toxicology and Applied Pharmacology. Vol. 18, Pg. 185, 1971.
rat LD50 intravenous 58880ug/kg (58.88mg/kg)   Drugs in Japan Vol. 6, Pg. 264, 1982.
rat LD50 oral 447mg/kg (447mg/kg)   Drugs in Japan Vol. 6, Pg. 264, 1982.
rat LDLo intraspinal 5mg/kg (5mg/kg) PERIPHERAL NERVE AND SENSATION: SPASTIC PARALYSIS WITH OR WITHOUT SENSORY CHANGE Acta Pharmacologica et Toxicologica. Vol. 56, Pg. 50, 1985.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 262.5 deg C   EXP
log P (octanol-water) 2.18 (none)   EXP
Water Solubility 2.00E+05 mg/L 25 EXP
Vapor Pressure 3.41E-05 mm Hg 25 EST
Henry's Law Constant 1.38E-08 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 7.71E-11 cm3/molecule-sec 25 EST

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