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Details

Stereochemistry RACEMIC
Molecular Formula C13H16ClNO
Molecular Weight 237.725
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of KETAMINE

SMILES

CNC1(CCCCC1=O)C2=CC=CC=C2Cl

InChI

InChIKey=YQEZLKZALYSWHR-UHFFFAOYSA-N
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

HIDE SMILES / InChI

Description

Ketamine (brand name Ketalar) is a cyclohexanone derivative used for induction of anesthesia. Ketalar is indicated as the sole anesthetic agent for diagnostic and surgical procedures that do not require skeletal muscle relaxation; also, it is indicated for the induction of anesthesia prior to the administration of other general anesthetic agents. Ketamine blocks NMDA receptors through an interaction with sites thought to be located within the ion channel pore region. However, the complete pharmacology of ketamine is more complex, and it is known to directly interact with a variety of other sites to varying degrees. Recently, it was shown that inclusion of the NR3B subunit does not alter the ketamine sensitivity of recombinant NR1/NR2 receptors expressed in oocytes. Likewise, 100 μM ketamine produced only weak inhibition of the glycine-induced current of NR1/NR3A/NR3B receptors. The side effects of ketamine noted in clinical studies include psychedelic symptoms (hallucinations, memory defects, panic attacks), nausea/vomiting, somnolence, cardiovascular stimulation and, in a minority of patients, hepatoxicity. The recreational use of ketamine is increasing and comes with a variety of additional risks ranging from bladder and renal complications to persistent psychotypical behaviour and memory defects. Ketamine was first synthesized in 1962 by Calvin Stevens at Parke-Davis Co (now Pfizer) as an alternative anesthetic to phencyclidine. It was first used in humans in 1965 by Corssen and Domino and was introduced into clinical practice by 1970.

CNS Activity

Originator

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
KETALAR
PubMed

PubMed

TitleDatePubMed
Ketamine-pancuronium-narcotic technic for cardiovascular surgery in infants--a comparative study.
1975 Nov-Dec
Electroencephalographic study of children during ketamine anesthesia.
1976
Effects of physostigmine, scopolamine, and mecamylamine on the sleeping time induced by ketamine in the rat.
1979 Mar 14
Venodilator effects of adenosine triphosphate and sodium nitroprusside; comparisons during controlled hypotension.
1987 Sep 1
Determination of absolute configuration of ketamine enantiomers by HPLC-CD-UV technique.
1999
Lack of pre-emptive analgesic effect of (R)-ketamine in laparoscopic cholecystectomy.
1999 Feb
[Complications of anesthesia and their prevention in children with spastic cerebral palsy during ambulatory surgery].
1999 Jul-Aug
[Ketamine].
1999 Mar
Prolonged analgesic effect of ketamine, an N-methyl-D-aspartate receptor inhibitor, in patients with chronic pain.
1999 May
Anticonvulsant efficacy of N-methyl-D-aspartate antagonists against convulsions induced by cocaine.
1999 May
Cognitive functions after pilocarpine-induced status epilepticus: changes during silent period precede appearance of spontaneous recurrent seizures.
1999 Sep
Ketamine: review of its pharmacology and its use in pediatric anesthesia.
1999 Winter
Cognitive, dissociative and psychotogenic effects of ketamine in recreational users on the night of drug use and 3 days later.
2000 Apr
Ketamine potentiates cerebrocortical damage induced by the common anaesthetic agent nitrous oxide in adult rats.
2000 Aug
Ketamine effects on eye movements.
2000 Dec
Differential effects of systemically administered ketamine and lidocaine on dynamic and static hyperalgesia induced by intradermal capsaicin in humans.
2000 Feb
Long-lasting hyperalgesia induced by fentanyl in rats: preventive effect of ketamine.
2000 Feb
Ketamine sedation for the reduction of children's fractures in the emergency department.
2000 Jul
Anesthesia induced retrograde amnesia is ameliorated by ephrinA5-IgG in mice: EphA receptor tyrosine kinases are involved in mammalian memory.
2000 Mar
Peripheral lidocaine but not ketamine inhibits capsaicin-induced hyperalgesia in humans.
2000 Oct
Analgesic effect of intravenous ketamine in cancer patients on morphine therapy: a randomized, controlled, double-blind, crossover, double-dose study.
2000 Oct
Midazolam attenuates ketamine-induced abnormal perception and thought process but not mood changes.
2000 Sep
Comparison of ketamine stereoisomers on tissue metabolic activity in an in vitro model of global cerebral ischaemia.
2001 Apr
In and out of the K-hole: a comparison of the acute and residual effects of ketamine in frequent and infrequent ketamine users.
2001 May
Interaction of intravenous anesthetics with recombinant human M1-M3 muscarinic receptors expressed in chinese hamster ovary cells.
2002 Dec
Ketamine in war/tropical surgery (a final tribute to the racemic mixture).
2002 May
Search of antimicrobial activity of selected non-antibiotic drugs.
2002 Nov-Dec
Cold allodynia and hyperalgesia in neuropathic pain: the effect of N-methyl-D-aspartate (NMDA) receptor antagonist ketamine--a double-blind, cross-over comparison with alfentanil and placebo.
2003 Feb
Effects of the 5-HT2A agonist psilocybin on mismatch negativity generation and AX-continuous performance task: implications for the neuropharmacology of cognitive deficits in schizophrenia.
2003 Jan
Double-blind randomized placebo-controlled trial of the effect of ketamine on postoperative morphine consumption in children following appendicectomy.
2003 Jun
Effects of different subanaesthetic doses of (S)-ketamine on psychopathology and binocular depth inversion in man.
2003 Mar
Phenyl-tetrazolyl acetophenones: discovery of positive allosteric potentiatiors for the metabotropic glutamate 2 receptor.
2004 Aug 26
[Expression of HSP70 induced by ketamine in the hippocampus of rat at different ages].
2004 Jul
Preemptive ketamine during general anesthesia for postoperative analgesia in patients undergoing laparoscopic cholecystectomy.
2004 Oct
Participation of adenosine system in the ketamine-induced motor activity in mice.
2005 Jan-Feb
Remifentanil-induced postoperative hyperalgesia and its prevention with small-dose ketamine.
2005 Jul
Safety of mixture of morphine with ketamine for postoperative patient-controlled analgesia: an audit with 1026 patients.
2005 Jul
Naloxone increases ketamine-induced hyperactivity in the open field in female rats.
2005 Jul
Patents

Sample Use Guides

In Vivo Use Guide
Intravenous Route: The initial dose of Ketalar (ketamine hydrochloride injection) administered intravenously may range from 1 mg/kg to 4.5 mg/kg (0.5 to 2 mg/lb). The average amount required to produce five to ten minutes of surgical anesthesia has been 2 mg/kg (1 mg/lb). Intramuscular Route: The initial dose of Ketalar administered intramuscularly may range from 6.5 to 13 mg/kg (3 to 6 mg/lb). A dose of 10 mg/kg (5 mg/lb) will usually produce 12 to 25 minutes of surgical anesthesia.
Route of Administration: intravenous; intramuscular
In Vitro Use Guide
Primary cultures of cortical neurons treated with ketamine (10 μM-10mM) at 3 days-in vitro (3 DIV) displayed a concentration-dependent decrease in expanded growth cones
Name Type Language
KETAMINE
HSDB   INN   MI   VANDF   WHO-DD  
INN  
Official Name English
NSC-70151
Code English
PMI-150
Code English
KETAFOL COMPONENT KETAMINE
Brand Name English
VETAKET
Brand Name English
CALYPSOL
Brand Name English
TEKAM
Brand Name English
CYCLOHEXANONE, 2-(2-CHLOROPHENYL)-2-(METHYLAMINO)-, (+/-)-
Systematic Name English
(+/-)-2-(O-CHLOROPHENYL)-2-(METHYLAMINO)CYCLOHEXANONE
Common Name English
(+/-)-KETAMINE
Common Name English
IMALGENE 1000
Brand Name English
KETASOL 100
Brand Name English
ANAKET V
Brand Name English
KETAMINE [WHO-DD]
Common Name English
KETAMINE [VANDF]
Common Name English
NARKETAN
Brand Name English
CYCLOHEXANONE, 2-(2-CHLOROPHENYL)-2-(METHYLAMINO)-
Systematic Name English
KETAMINE [MI]
Common Name English
URSOTAMIN
Brand Name English
CLORKETAM 1000
Brand Name English
DL-KETAMINE
Common Name English
KETAMINE [INN]
Common Name English
KETAMINE [HSDB]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C245
Created by admin on Mon Oct 21 20:32:24 UTC 2019 , Edited by admin on Mon Oct 21 20:32:24 UTC 2019
CFR 21 CFR 522.1222A
Created by admin on Mon Oct 21 20:32:24 UTC 2019 , Edited by admin on Mon Oct 21 20:32:24 UTC 2019
NDF-RT N0000175681
Created by admin on Mon Oct 21 20:32:24 UTC 2019 , Edited by admin on Mon Oct 21 20:32:24 UTC 2019
FDA ORPHAN DRUG 288809
Created by admin on Mon Oct 21 20:32:24 UTC 2019 , Edited by admin on Mon Oct 21 20:32:24 UTC 2019
WHO-VATC QN01AX03
Created by admin on Mon Oct 21 20:32:24 UTC 2019 , Edited by admin on Mon Oct 21 20:32:24 UTC 2019
WHO-ESSENTIAL MEDICINES LIST 1.1.2
Created by admin on Mon Oct 21 20:32:24 UTC 2019 , Edited by admin on Mon Oct 21 20:32:24 UTC 2019
DEA NO. 7285
Created by admin on Mon Oct 21 20:32:24 UTC 2019 , Edited by admin on Mon Oct 21 20:32:24 UTC 2019
NDF-RT N0000175975
Created by admin on Mon Oct 21 20:32:24 UTC 2019 , Edited by admin on Mon Oct 21 20:32:24 UTC 2019
WHO-ATC N01AX03
Created by admin on Mon Oct 21 20:32:24 UTC 2019 , Edited by admin on Mon Oct 21 20:32:24 UTC 2019
LIVERTOX 531
Created by admin on Mon Oct 21 20:32:24 UTC 2019 , Edited by admin on Mon Oct 21 20:32:24 UTC 2019
Code System Code Type Description
HSDB
6740-88-1
Created by admin on Mon Oct 21 20:32:24 UTC 2019 , Edited by admin on Mon Oct 21 20:32:24 UTC 2019
PRIMARY
INN
2156
Created by admin on Mon Oct 21 20:32:24 UTC 2019 , Edited by admin on Mon Oct 21 20:32:24 UTC 2019
PRIMARY
DRUG BANK
DB01221
Created by admin on Mon Oct 21 20:32:24 UTC 2019 , Edited by admin on Mon Oct 21 20:32:24 UTC 2019
PRIMARY
PUBCHEM
3821
Created by admin on Mon Oct 21 20:32:24 UTC 2019 , Edited by admin on Mon Oct 21 20:32:24 UTC 2019
PRIMARY
EVMPD
SUB08365MIG
Created by admin on Mon Oct 21 20:32:24 UTC 2019 , Edited by admin on Mon Oct 21 20:32:24 UTC 2019
PRIMARY
CAS
6740-88-1
Created by admin on Mon Oct 21 20:32:24 UTC 2019 , Edited by admin on Mon Oct 21 20:32:24 UTC 2019
PRIMARY
ChEMBL
CHEMBL742
Created by admin on Mon Oct 21 20:32:24 UTC 2019 , Edited by admin on Mon Oct 21 20:32:24 UTC 2019
PRIMARY
ECHA (EC/EINECS)
229-804-1
Created by admin on Mon Oct 21 20:32:24 UTC 2019 , Edited by admin on Mon Oct 21 20:32:24 UTC 2019
PRIMARY
CAS
33643-45-7
Created by admin on Mon Oct 21 20:32:24 UTC 2019 , Edited by admin on Mon Oct 21 20:32:24 UTC 2019
SUPERSEDED
CAS
100477-72-3
Created by admin on Mon Oct 21 20:32:24 UTC 2019 , Edited by admin on Mon Oct 21 20:32:24 UTC 2019
SUPERSEDED
IUPHAR
4233
Created by admin on Mon Oct 21 20:32:24 UTC 2019 , Edited by admin on Mon Oct 21 20:32:24 UTC 2019
PRIMARY
RXCUI
6130
Created by admin on Mon Oct 21 20:32:24 UTC 2019 , Edited by admin on Mon Oct 21 20:32:24 UTC 2019
PRIMARY RxNorm
LactMed
6740-88-1
Created by admin on Mon Oct 21 20:32:24 UTC 2019 , Edited by admin on Mon Oct 21 20:32:24 UTC 2019
PRIMARY
CAS
79499-51-7
Created by admin on Mon Oct 21 20:32:24 UTC 2019 , Edited by admin on Mon Oct 21 20:32:24 UTC 2019
SUPERSEDED
NCI_THESAURUS
C61797
Created by admin on Mon Oct 21 20:32:24 UTC 2019 , Edited by admin on Mon Oct 21 20:32:24 UTC 2019
PRIMARY
MESH
D007649
Created by admin on Mon Oct 21 20:32:24 UTC 2019 , Edited by admin on Mon Oct 21 20:32:24 UTC 2019
PRIMARY
EPA CompTox
6740-88-1
Created by admin on Mon Oct 21 20:32:24 UTC 2019 , Edited by admin on Mon Oct 21 20:32:24 UTC 2019
PRIMARY
MERCK INDEX
M6613
Created by admin on Mon Oct 21 20:32:24 UTC 2019 , Edited by admin on Mon Oct 21 20:32:24 UTC 2019
PRIMARY Merck Index
WIKIPEDIA
KETAMINE
Created by admin on Mon Oct 21 20:32:24 UTC 2019 , Edited by admin on Mon Oct 21 20:32:24 UTC 2019
PRIMARY