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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

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
KETALAR

Cmax

ValueDoseCo-administeredAnalytePopulation
2104 ng/mL
9 mg/kg single, nasal
KETAMINE plasma
Homo sapiens
496 ng/mL
3 mg/kg single, nasal
KETAMINE plasma
Homo sapiens
632 ng/mL
9 mg single, rectal
KETAMINE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
148.3 mg × min/L
3 mg/kg single, intravenous
KETAMINE plasma
Homo sapiens
163.6 mg × min/L
9 mg/kg single, nasal
KETAMINE plasma
Homo sapiens
76.4 mg × min/L
3 mg/kg single, nasal
KETAMINE plasma
Homo sapiens
111.2 ng × min/mL
9 mg single, rectal
KETAMINE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
125 min
3 mg/kg single, intravenous
KETAMINE plasma
Homo sapiens
120 min
9 mg/kg single, nasal
KETAMINE plasma
Homo sapiens
123 min
3 mg/kg single, nasal
KETAMINE plasma
Homo sapiens
100 min
9 mg single, rectal
KETAMINE plasma
Homo sapiens

Doses

AEs

Overview

OverviewOther

Other InhibitorOther SubstrateOther Inducer






Drug as perpetrator​

Drug as victim

Tox targets

PubMed

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: Other
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