(RS)-ketamine

Also known as DL-ketamine, 2-(o-chlorophenyl)-2-(methylamino)-cyclohexanone, 2-(methylamino)-2-(2-chlorophenyl)cyclohexanone, (±)-ketamine, 2-(2-chloro-phenyl)-2-methylamino-cyclohexanone, (+-)-ketamine, special K, Special K

Ketamine is a cyclohexanone-derived general anesthetic and NMDA receptor antagonist with analgesic and hallucinogenic properties, used medically for anesthesia, depression, and pain management. Ketamine exists as its two enantiomers, S- (esketamine) and R- (arketamine), and has antidepressant action likely involving other mechanisms in addition to NMDA antagonism.

AI overview

(RS)-ketamine is a mixture of two mirror-image forms of the anesthetic drug ketamine, which works by blocking a type of brain receptor called NMDA and has pain-relieving and mood-lifting effects. It's used medically for anesthesia, treating depression, and managing pain, though scientists believe its antidepressant benefits involve more than just its main mechanism of action.

AI-generated from the Wikipedia summary — may contain errors.

In the Vinony graph

Within Vinony's link graph, (RS)-ketamine is referenced by 3,514 other articles, and connects out to drug liberalization, allosteric modulator and valproic acid.

Vinony files it under 2-Chlorophenyl compounds, Analgesics and Antidepressants.

Its subject is documented across 72 Wikipedia language editions.

Key facts

Drug.C: 13
Drug.Watchedfields: changed
Drug.verifiedrevid: 477168837
Drug.image: Ketamine2DCSD.svg
Drug.image_class: skin-invert-image
Drug.width: 150px
Drug.image2: S-ketamine-from-HCl-xtal-3D-balls.png
Drug.image_class2: bg-transparent
Drug.width2: 175px
Drug.alt2: (S)-Ketamine ball-and-stick model
Drug.tradename: Ketalar, others
Drug.DailyMedID: Ketamine
Drug.pregnancy_AU: B3
Drug.addiction_liability: Moderate–high
Drug.routes_of_administration: Any
Drug.class: NMDA receptor antagonist; general anesthetic; dissociative hallucinogen; analgesic; antidepressant
Drug.ATC_prefix: N01
Drug.ATC_suffix: AX03

via Wikipedia infobox

Chemical data

Formula: C13H16ClNO
Molecular weight: 237.72 g/mol
IUPAC name: 2-(2-chlorophenyl)-2-(methylamino)cyclohexan-1-one
SMILES: CNC1(CCCCC1=O)C2=CC=CC=C2Cl
InChIKey: YQEZLKZALYSWHR-UHFFFAOYSA-N
XLogP: 2.2
Polar surface area: 29.1 Å²
H-bond donors: 1
H-bond acceptors: 2
Formal charge: 0

via PubChem

Research

6 papers

Pharmacokinetics of S-ketamine and R-ketamine and their active metabolites after racemic ketamine or S-ketamine intravenous administration in dogs sedated with medetomidine.Veterinary anaesthesia and analgesia · 2020Romagnoli N, Bektas RN, Kutter APN et al.DOI: 10.1016/j.vaa.2019.08.048
Stereoselective Ketamine Metabolism by Genetic Variants of Cytochrome P450 CYP2B6 and Cytochrome P450 Oxidoreductase.Anesthesiology · 2018Wang PF, Neiner A, Kharasch EDDOI: 10.1097/ALN.0000000000002371
Subarachnoid ketamine and ketamine s (+) associated with lidocaine in sheep and goats anesthesia.Veterinary and animal science · 2021Dória RGS, Ferraz GRL, Filippo PAD et al.DOI: 10.1016/j.vas.2020.100148
Differential role of nitric oxide in the psychedelic symptoms induced by racemic ketamine and esketamine in human volunteers.British journal of anaesthesia · 2018Jonkman K, van der Schrier R, van Velzen M et al.DOI: 10.1016/j.bja.2018.01.022
Cognitive Impairment That Is Induced by (R)-Ketamine Is Abolished in NMDA GluN2D Receptor Subunit Knockout Mice.The international journal of neuropsychopharmacology · 2019Ide S, Ikekubo Y, Mishina M et al.DOI: 10.1093/ijnp/pyz025
Role of NMDA receptor GluN2D subunit in the antidepressant effects of enantiomers of ketamine.Journal of pharmacological sciences · 2017Ide S, Ikekubo Y, Mishina M et al.DOI: 10.1016/j.jphs.2017.11.001

via PubMed

Wikidata facts

Mass: 237.092042

Show 4 more facts

Commons category: Ketamine
chemical formula: C₁₃H₁₆ClNO
canonical SMILES: CNC1(CCCCC1=O)C2=CC=CC=C2Cl
World Health Organisation international non-proprietary name: 氯胺酮

Sources (9)

via Wikidata · CC0

~33 min read

Encyclopedic overview

30 sections

Contents

Medical uses
Anesthesia
Pain
Depression
Seizures
Asthma
Contraindications
Adverse effects
Liver toxicity and urologic disease
Near-death experience
Addiction and tolerance
Brain damage
Interactions
Pharmacology
Pharmacodynamics
Mechanism of action
Molecular targets
Relationships between levels and effects
Pharmacokinetics
Chemistry
Structure
Detection
History
Society and culture
Legal status
Recreational use
Research
Veterinary uses
References
External links

At anesthetic doses, ketamine induces a state of dissociative anesthesia, a trance-like state providing pain relief, sedation, and amnesia. Its distinguishing features as an anesthetic are preserved breathing and airway reflexes, stimulated heart function with increased blood pressure, and moderate bronchodilation. As an anesthetic, it is used especially in trauma, emergency, and pediatric cases. At lower, sub-anesthetic doses, it is used as a treatment for pain and treatment-resistant depression.

Excerpted from Wikipedia’s “(RS)-ketamine” article, available under the CC BY-SA 4.0 licence.