ketamine   Click here for help

GtoPdb Ligand ID: 4233

Synonyms: Ketalar | ketamine HCl
Approved drug
ketamine is an approved drug (FDA (1970))
Compound class: Synthetic organic
Comment: Ketamine is a rapidly acting ionotropic glutamate channel blocker with broad therapeutic application, approved in 1970. The structure shown is the racemate that is also used as the hydrochloride PubChem CID 15851. Of the two ketamine enantiomers, esketamine (S enantiomer) is being developed as a drug in its own right, but the less active arketamine (R enantiomer) is not. A recent report (Nature April 2016) implicated certain ketamine metabolites and their stereoisomers in different mechanisms of action [3]. In particular, (2R,6R) 6-hydroxynorketamine seems to be responsible for NMDAR-independent antidepressant effects. The Nature paper authors filed a patent including some of the data [2].
Ketamine is on the World Health Organisation's List of Essential Medicines. Click here to access the pdf version of the WHO's 21st Essential Medicines list (2019).
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species

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View more information in the IUPHAR Pharmacology Education Project: ketamine

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 2
Hydrogen bond donors 1
Rotatable bonds 2
Topological polar surface area 29.1
Molecular weight 237.09
XLogP 2.88
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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Canonical SMILES CNC1(CCCCC1=O)c1ccccc1Cl
Isomeric 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
InChI Key YQEZLKZALYSWHR-UHFFFAOYSA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1970))
WHO Essential Medicine WHO Essential Medicines List (EML) (23rd List, 2023). Access PDF version.
Click to view more information about the WHO Model Lists of Essential Medicines.
IUPAC Name Click here for help
2-(2-chlorophenyl)-2-(methylamino)cyclohexan-1-one
International Nonproprietary Names Click here for help
INN number INN
2156 ketamine
Synonyms Click here for help
Ketalar | ketamine HCl
Database Links Click here for help
CAS Registry No. 6740-88-1 (source: Scifinder)
ChEMBL Ligand CHEMBL742
DrugBank Ligand DB01221
DrugCentral Ligand 1523
GtoPdb PubChem SID 178101050
PubChem CID 3821
Search Google for chemical match using the InChIKey YQEZLKZALYSWHR-UHFFFAOYSA-N
Search Google for chemicals with the same backbone YQEZLKZALYSWHR
Search PubMed clinical trials ketamine
Search PubMed titles ketamine
Search PubMed titles/abstracts ketamine
UniChem Compound Search for chemical match using the InChIKey YQEZLKZALYSWHR-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey YQEZLKZALYSWHR-UHFFFAOYSA-N
Wikipedia Ketamine