2-(2-chlorophenyl)-2-(methylamino)cyclohexan-1-one

• ChemBase ID: 1091
• Molecular Formular: C13H16ClNO
• Molecular Mass: 237.72524
• Monoisotopic Mass: 237.09204182
• SMILES: Clc1c(C2(NC)CCCCC2=O)cccc1
• Canonical SMILES: CNC1(CCCCC1=O)c1ccccc1Cl
• InChI: InChI=1S/C13H16ClNO/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
• InChIKey: YQEZLKZALYSWHR-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(2-chlorophenyl)-2-(methylamino)cyclohexan-1-one
• IUPAC Traditional name: (+-)-ketamine; ketamine
• Brand Name: CLSTA 20; Esketamine; Ketaject; Ketalar; Ketalar base; Ketanest; Ketolar
• Synonyms: (-)-Ketamine; (S)-(-)-Ketamine; (S)-Ketamine; CI 581 base; Ketamine HCL; Ketamine Base; l-Ketamine; Ketamine

Database IDs

• CAS Number: 6740-88-1
• PubChem SID: 160964554; 46508295
• PubChem CID: 3821
• CHEBI ID: 6121
• ATC CODE: N01AX03
• CHEMBL: 742
• Chemspider ID: 3689
• DrugBank ID: DB01221
• KEGG ID: D08098
• Unique Ingredient Identifier: 690G0D6V8H
• Wikipedia Title: Ketamine

CALCULATED PROPERTIES

JChem

• Acid pKa: 18.783304
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 1.4100732
• LogD (pH = 7.4): 3.0185769
• Log P: 3.3473027
• Molar Refractivity: 65.5538 cm^3
• Polarizability: 25.949158 Å^3
• Polar Surface Area: 29.1 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.69
• LOG S: -3.71
• Solubility (Water): 4.64e-02 g/l

PROPERTIES

Physical Property

• Melting Point: 262°C (503.6°F)
• Hydrophobicity(logP): 2.9

Pharmacology Properties

• Admin Routes: IV, IM, Insufflated, oral, topical
• Dependency Liability: Medium
• Excretion: renal (>90%)
• Half Life: 2.5–3 hours.
• Metabolism: Hepatic, primarily by CYP3A4
• Legal Status: CD (UK); S8 (Australia); Schedule I (Canada); Schedule III (US)
• Pregnancy Category: B

DETAILS

DrugBank - DB01221

• Drug Groups: approved
• Description: 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. [PubChem]
• Indication: For use as the sole anesthetic agent for diagnostic and surgical procedures that do not require skeletal muscle relaxation.
• Pharmacology: Ketamine is a rapid-acting general anesthetic producing an anesthetic state characterized by profound analgesia, normal pharyngeal-laryngeal reflexes, normal or slightly enhanced skeletal muscle tone, cardiovascular and respiratory stimulation, and occasionally a transient and minimal respiratory depression. Ketamine is indicated as the sole anesthetic agent for diagnostic and surgical procedures that do not require skeletal muscle relaxation. The anesthetic state produced by Ketamine has been termed “dissociative anesthesia” in that it appears to selectively interrupt association pathways of the brain before producing somesthetic sensory blockade. It may selectively depress the thalamoneocortical system before significantly obtunding the more ancient cerebral centers and pathways (reticularactivating and limbic systems).
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic.
• Absorption: Rapidly absorbed following parenteral administration.
• Half Life: 2.5-3 hours.
• References: Harrison NL, Simmonds MA: Quantitative studies on some antagonists of N-methyl D-aspartate in slices of rat cerebral cortex. Br J Pharmacol. 1985 Feb;84(2):381-91. [Pubmed] ; Bergman SA: Ketamine: review of its pharmacology and its use in pediatric anesthesia. Anesth Prog. 1999 Winter;46(1):10-20. [Pubmed] ; Bonanno FG: Ketamine in war/tropical surgery (a final tribute to the racemic mixture). Injury. 2002 May;33(4):323-7. [Pubmed] ; Lankenau SE, Sanders B, Bloom JJ, Hathazi D, Alarcon E, Tortu S, Clatts MC: First injection of ketamine among young injection drug users (IDUs) in three U.S. cities. Drug Alcohol Depend. 2007 Mar 16;87(2-3):183-93. Epub 2006 Sep 18. [Pubmed] ; Reboso Morales JA, Gonzalez Miranda F: [Ketamine] Rev Esp Anestesiol Reanim. 1999 Mar;46(3):111-22. [Pubmed]
• External Links: Wikipedia; RxList; Drugs.com

REFERENCES

• Harrison NL, Simmonds MA: Quantitative studies on some antagonists of N-methyl D-aspartate in slices of rat cerebral cortex. Br J Pharmacol. 1985 Feb;84(2):381-91. Pubmed
• Bergman SA: Ketamine: review of its pharmacology and its use in pediatric anesthesia. Anesth Prog. 1999 Winter;46(1):10-20. Pubmed
• Bonanno FG: Ketamine in war/tropical surgery (a final tribute to the racemic mixture). Injury. 2002 May;33(4):323-7. Pubmed
• Lankenau SE, Sanders B, Bloom JJ, Hathazi D, Alarcon E, Tortu S, Clatts MC: First injection of ketamine among young injection drug users (IDUs) in three U.S. cities. Drug Alcohol Depend. 2007 Mar 16;87(2-3):183-93. Epub 2006 Sep 18. Pubmed
• Reboso Morales JA, Gonzalez Miranda F: [Ketamine] Rev Esp Anestesiol Reanim. 1999 Mar;46(3):111-22. Pubmed