(S)-Ketamine (CED0003797)

Record Information

Version

1.0

Creation Date

2016-05-22 06:20:52 UTC

Update Date

2026-05-14 19:13:29 UTC

SynCED ID

CED0003797

Secondary Accession Numbers

CHEM019626

Identification

Common Name

(S)-Ketamine

Class

Small Molecule

Description

(S)-Ketamine is an organic compound with the formula C13H16ClNO and an average molecular weight of 237.73 g/mol. (S)-Ketamine belongs to the halobenzenes, a subclass of benzene and substituted derivatives within the organic compounds. This compound is found in or released from two recorded sources: healthcare, pharmaceuticals, and veterinary products, specifically as antidepressants and anesthetics. The recorded route of exposure for this substance is nasal. (S)-Ketamine interacts with ten recorded protein targets, acting as an agonist, antagonist, inhibitor, or upregulator. These targets include the glutamate receptor ionotropic, NMDA 1 (GRIN1), glutamate receptor ionotropic, NMDA 2A (GRIN2A), glutamate receptor ionotropic, NMDA 2D (GRIN2D), and glutamate receptor ionotropic, NMDA 3B (GRIN3B), in addition to six other proteins.

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(-)-Ketamine	ChEBI
(S)-(-)-Ketamine	ChEBI
(S)-2-(O-Chlorophenyl)-2-(methylamino)cyclohexanone	ChEBI
(S)-Ketamine	ChEBI
S-Ketamine	MeSH
L-Ketamine	MeSH
Kataved	MeSH

Chemical Formula

C₁₃H₁₆ClNO

Average Molecular Mass

237.730 g/mol

Monoisotopic Mass

237.092 g/mol

CAS Registry Number

33643-46-8

IUPAC Name

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

Traditional Name

esketamine

SMILES

CN[C@@]1(CCCCC1=O)C1=CC=CC=C1Cl

InChI Identifier

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/t13-/m0/s1

InChI Key

YQEZLKZALYSWHR-ZDUSSCGKSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as chlorobenzenes. Chlorobenzenes are compounds containing one or more chlorine atoms attached to a benzene moiety.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Halobenzenes

Direct Parent

Chlorobenzenes

Alternative Parents

Substituents

Chlorobenzene
Aralkylamine
Aryl chloride
Aryl halide
Ketone
Cyclic ketone
Secondary aliphatic amine
Secondary amine
Amine
Organooxygen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Carbonyl group
Organic oxygen compound
Organic nitrogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

ketamine (CHEBI:60799 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.046 g/L	ALOGPS
logP	2.69	ALOGPS
logP	3.35	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	18.8	ChemAxon
pKa (Strongest Basic)	7.16	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	29.1 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	65.55 m³·mol⁻¹	ChemAxon
Polarizability	24.97 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-000i-0190000000-d3addd1c61dae1965d68	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-000i-2490000000-4b32229520af03c01035	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0uy0-3900000000-f31baf727a934e3e0c6f	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-000i-0090000000-3166c540bb2a7f57489e	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-000i-0390000000-f6a156602d423ed34dc1	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0229-8920000000-d5d51aef2ac12188e9e8	Not Available	View Spectrum

Toxicity Profile

Toxicity Values

Toxicity Value	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Toxicity Rating	Reference
232.0 Log mg/kg [130:410]	Rat	LD50	oral	predicted	Not Available	Not Available

Toxicity / Toxin Class

Not Available

Mechanism of Toxicity

Not Available

Carcinogenicity (IARC Classification)

Not Available

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Health Effects

Health Effect	Relationship	Direction	Description	Reference
pain agnosia	Has Therapeutic Effect On	Not Available	Not Available	PMC5943951
Depressive Disorder, Treatment-Resistant	Not Available	Not Available	Not Available	PMC11978337

Exposure Sources

Source ID	Source	Sector	Reference
CEDs000369	Anesthetics?Anesthetics are synthetic chemicals used to induce loss of sensation or consciousness in patients undergoing medical procedures.	Healthcare, pharmaceuticals & veterinary products	Not Available
CEDs000377	Antidepressants?Antidepressants, a class of synthetic chemicals designed to alleviate symptoms of depression and anxiety, can enter the environment through various pathways, leading to contamination of water systems.	Healthcare, pharmaceuticals & veterinary products	Not Available
CEDs000696	Nanotechnology?Nanotechnology involves the manipulation of materials at the molecular or atomic level, typically within the range of 1 to 100 nanometers.	Industrial manufacturing & chemical processing	PubChem

Pathways

0 pathwaysPathway Source: PathBank

No pathways found

No metabolic pathways have been associated with this synthetic chemical

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Cholinesterase	P81908	Equus caballus	Predicted (SEA)	Prediction Confidence Score 0.378 Applicability Domain 1.0 Statistical Significance 0.007 Supporting Reference Compounds 201 E-value 54.3388
Click to view 3D structure	Acetylcholinesterase	O42275	Electrophorus electricus	Predicted (SEA)	Prediction Confidence Score 0.376 Applicability Domain 1.0 Statistical Significance 0.0073 Supporting Reference Compounds 206 E-value 56.9078
Click to view 3D structure	Acetylcholine receptor subunit alpha	P02710	Torpedo californica	Predicted (SEA)	Prediction Confidence Score 0.35 Applicability Domain 1.0 Statistical Significance 1.00e-05 Supporting Reference Compounds 11 E-value 0.0778492
Click to view 3D structure	Voltage-dependent L-type calcium channel subunit alpha-1C	Q13936	Humans	Predicted (SEA)	Prediction Confidence Score 0.333 Applicability Domain 1.0 Statistical Significance 0.0013 Supporting Reference Compounds 71 E-value 10.3539
Click to view 3D structure	Alpha-1A adrenergic receptor	P43140	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.263 Applicability Domain 0.288 Low confidence Statistical Significance 0.0559 Supporting Reference Compounds 208 E-value 434.866
Click to view 3D structure	1-deoxy-D-xylulose-5-phosphate synthase, chloroplastic	Q38854	Arabidopsis thaliana	Predicted (SEA)	Prediction Confidence Score 0.25 Applicability Domain 0.25 Low confidence Statistical Significance 0.0012 Supporting Reference Compounds 1 E-value 9.6533
Click to view 3D structure	Coproporphyrinogen III oxidase	P32397	Bacillus subtilis (strain 168)	Predicted (SEA)	Prediction Confidence Score 0.246 Applicability Domain 0.246 Low confidence Statistical Significance 0.0031 Supporting Reference Compounds 1 E-value 24.0554
Click to view 3D structure	Alpha-1B adrenergic receptor	P35368	Humans	Predicted (SEA)	Prediction Confidence Score 0.245 Applicability Domain 0.286 Low confidence Statistical Significance 0.1337 Supporting Reference Compounds 298 E-value 1041.0
Click to view 3D structure	Sodium-dependent noradrenaline transporter	P23975	Humans	Predicted (SEA)	Prediction Confidence Score 0.245 Applicability Domain 0.288 Low confidence Statistical Significance 0.1861 Supporting Reference Compounds 451 E-value 1448.62
Click to view 3D structure	5-hydroxytryptamine receptor 1A	P08908	Humans	Predicted (SEA)	Prediction Confidence Score 0.242 Applicability Domain 0.286 Low confidence Statistical Significance 0.3346 Supporting Reference Compounds 953 E-value 2604.99
Click to view 3D structure	Alpha-2C adrenergic receptor	P18825	Humans	Predicted (SEA)	Prediction Confidence Score 0.24 Applicability Domain 0.265 Low confidence Statistical Significance 0.1647 Supporting Reference Compounds 386 E-value 1282.41
Click to view 3D structure	Alpha-1D adrenergic receptor	P23944	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.24 Applicability Domain 0.286 Low confidence Statistical Significance 0.0555 Supporting Reference Compounds 105 E-value 432.452
Click to view 3D structure	Sodium-dependent serotonin transporter	P31645	Humans	Predicted (SEA)	Prediction Confidence Score 0.24 Applicability Domain 0.288 Low confidence Statistical Significance 0.2665 Supporting Reference Compounds 593 E-value 2074.99
Click to view 3D structure	Sodium-dependent serotonin transporter	P31652	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.238 Applicability Domain 0.288 Low confidence Statistical Significance 0.1441 Supporting Reference Compounds 297 E-value 1121.96
Click to view 3D structure	Alpha-1A adrenergic receptor	P35348	Humans	Predicted (SEA)	Prediction Confidence Score 0.236 Applicability Domain 0.271 Low confidence Statistical Significance 0.2262 Supporting Reference Compounds 376 E-value 1761.11
Click to view 3D structure	Cytochrome P450 3A4	P08684	Humans	Predicted (SEA)	Prediction Confidence Score 0.234 Applicability Domain 0.245 Low confidence Statistical Significance 0.7343 Supporting Reference Compounds 1538 E-value 5716.7
Click to view 3D structure	Glycogen synthase kinase-3 beta	P49841	Humans	Predicted (SEA)	Prediction Confidence Score 0.233 Applicability Domain 0.25 Low confidence Statistical Significance 0.5824 Supporting Reference Compounds 1157 E-value 4533.94
Click to view 3D structure	D(2) dopamine receptor	P14416	Humans	Predicted (SEA)	Prediction Confidence Score 0.232 Applicability Domain 0.245 Low confidence Statistical Significance 0.4796 Supporting Reference Compounds 1103 E-value 3733.73
Click to view 3D structure	Cytochrome P450 2D6	P10635	Humans	Predicted (SEA)	Prediction Confidence Score 0.232 Applicability Domain 0.242 Low confidence Statistical Significance 0.6731 Supporting Reference Compounds 1130 E-value 5240.03
Click to view 3D structure	Sodium-dependent dopamine transporter	Q01959	Humans	Predicted (SEA)	Prediction Confidence Score 0.231 Applicability Domain 0.245 Low confidence Statistical Significance 0.3583 Supporting Reference Compounds 506 E-value 2789.26
Click to view 3D structure	Cytochrome P450 2C9	P11712	Humans	Predicted (SEA)	Prediction Confidence Score 0.231 Applicability Domain 0.242 Low confidence Statistical Significance 0.7293 Supporting Reference Compounds 1245 E-value 5677.47
Click to view 3D structure	Alpha-2B adrenergic receptor	P18089	Humans	Predicted (SEA)	Prediction Confidence Score 0.231 Applicability Domain 0.245 Low confidence Statistical Significance 0.2285 Supporting Reference Compounds 340 E-value 1778.62
Click to view 3D structure	Sigma non-opioid intracellular receptor 1	Q99720	Humans	Predicted (SEA)	Prediction Confidence Score 0.23 Applicability Domain 0.245 Low confidence Statistical Significance 0.3764 Supporting Reference Compounds 562 E-value 2929.93
Click to view 3D structure	Voltage-gated inwardly rectifying potassium channel KCNH2	Q12809	Humans	Predicted (SEA)	Prediction Confidence Score 0.23 Applicability Domain 0.239 Low confidence Statistical Significance 0.7637 Supporting Reference Compounds 1498 E-value 5945.58
Click to view 3D structure	D(1A) dopamine receptor	P21728	Humans	Predicted (SEA)	Prediction Confidence Score 0.229 Applicability Domain 0.245 Low confidence Statistical Significance 0.2902 Supporting Reference Compounds 425 E-value 2259.26