Record Information |
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Version | 2.0 |
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Creation Date | 2009-07-21 20:28:40 UTC |
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Update Date | 2014-12-24 20:25:56 UTC |
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Accession Number | T3D3025 |
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Identification |
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Common Name | Ketamine |
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Class | Small Molecule |
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Description | Ketamine is only found in individuals that have used or taken this drug. It is a cyclohexanone derivative used for induction of anesthesia. Its mechanism of action is not well understood, but ketamine can block NMDA receptors (receptors, N-methyl-D-aspartate) and may interact with sigma receptors. [PubChem] Ketamine has several clinically useful properties, including analgesia and less cardiorespiratory depressant effects than other anaesthetic agents, it also causes some stimulation of the cardiocascular system. Ketamine has been reported to produce general as well as local anaesthesia. It interacts with N-methyl-D-aspartate (NMDA) receptors, opioid receptors, monoaminergic receptors, muscarinic receptors and voltage sensitive Ca ion channels. Unlike other general anaesthetic agents, ketamine does not interact with GABA receptors. |
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Compound Type | - Amine
- Analgesic
- Anesthetic
- Anesthetic, Dissociative
- Drug
- Excitatory Amino Acid Antagonist
- General Anesthetic
- Metabolite
- Organic Compound
- Organochloride
- Synthetic Compound
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Chemical Structure | |
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Synonyms | Synonym | (+-)-Ketamine | (-)-Ketamine | (S)-(-)-Ketamine | (S)-Ketamine | (±)-ketamine | 2-(2-Chloro-phenyl)-2-methylamino-cyclohexanone | 2-(methylamino)-2-(2-chlorophenyl)cyclohexanone | 2-(o-chlorophenyl)-2-(methylamino)-cyclohexanone | CI 581 base | DL-ketamine | Ketaject | Ketalar | Ketamina | KETAMINE | Ketamine Base | Ketamine HCL | Ketaminum | Ketanest | L-Ketamine | NMDA | Special k |
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Chemical Formula | C13H16ClNO |
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Average Molecular Mass | 237.725 g/mol |
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Monoisotopic Mass | 237.092 g/mol |
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CAS Registry Number | 6740-88-1 |
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IUPAC Name | 2-(2-chlorophenyl)-2-(methylamino)cyclohexan-1-one |
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Traditional Name | ketamine |
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SMILES | CNC1(CCCCC1=O)C1=CC=CC=C1Cl |
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InChI Identifier | InChI=1/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 |
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InChI Key | InChIKey=YQEZLKZALYSWHR-UHFFFAOYNA-N |
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Chemical Taxonomy |
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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. |
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Kingdom | Organic compounds |
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Super Class | Benzenoids |
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Class | Benzene and substituted derivatives |
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Sub Class | Halobenzenes |
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Direct Parent | Chlorobenzenes |
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Alternative Parents | |
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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
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Molecular Framework | Aromatic homomonocyclic compounds |
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External Descriptors | |
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Biological Properties |
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Status | Detected and Not Quantified |
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Origin | Exogenous |
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Cellular Locations | |
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Biofluid Locations | Not Available |
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Tissue Locations | Not Available |
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Pathways | Not Available |
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Applications | |
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Biological Roles | |
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Chemical Roles | Not Available |
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Physical Properties |
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State | Solid |
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Appearance | White powder. |
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Experimental Properties | Property | Value |
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Melting Point | 92-93°C | Boiling Point | Not Available | Solubility | 4.64e-02 g/L | LogP | 2.9 |
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Predicted Properties | |
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Spectra |
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Spectra | Spectrum Type | Description | Splash Key | Deposition Date | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0ue9-1900000000-137b9855ffed670aa9f4 | 2017-09-01 | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-004i-0930000000-8216e02922628a5070cf | 2017-09-14 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-00di-0090000000-7704dbbfa717abc4bab2 | 2017-09-14 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-000i-0090000000-aff2b684d97275321043 | 2017-09-14 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-000i-0290000000-1707dec51cc3e89964c9 | 2017-09-14 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-004i-0940000000-59871faec16835eb1b3a | 2017-09-14 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-004i-0900000000-ca62e82b4a1dfb81b3b0 | 2017-09-14 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-004i-0900000000-6c243d7b1c2e8cf69efa | 2017-09-14 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-004i-0900000000-441a423105753e2c8b9c | 2017-09-14 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-000i-0090000000-24585e7c2431b3b9319e | 2017-09-14 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-000i-0290000000-c9d734b085ec94dabd9a | 2017-09-14 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-004i-0940000000-054d77385726d4e35e20 | 2017-09-14 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-004i-0900000000-8c263bb521fb6ebe6cac | 2017-09-14 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-004i-0900000000-702873d66ce0d419711d | 2017-09-14 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-004i-0900000000-e23ba411aa96df9b5d6f | 2017-09-14 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-00di-0090000000-5f14196db213c95f3e71 | 2017-09-14 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-000i-0090000000-85385cf96aa2ac05921a | 2017-09-14 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-05br-0390000000-9177663a5915fac51aa7 | 2017-09-14 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-004i-0910000000-d00d242dae695dc5aff9 | 2017-09-14 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-004i-0900000000-95c2a8805f1587266fea | 2017-09-14 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-000i-0190000000-d3addd1c61dae1965d68 | 2016-08-03 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-000i-2490000000-4b32229520af03c01035 | 2016-08-03 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0uy0-3900000000-f31baf727a934e3e0c6f | 2016-08-03 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-000i-0090000000-3166c540bb2a7f57489e | 2016-08-03 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-000i-0390000000-f6a156602d423ed34dc1 | 2016-08-03 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0229-8920000000-d5d51aef2ac12188e9e8 | 2016-08-03 | View Spectrum |
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Toxicity Profile |
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Route of Exposure | Rapidly absorbed following parenteral administration. |
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Mechanism of Toxicity | Ketamine has several clinically useful properties, including analgesia and less cardiorespiratory depressant effects than other anaesthetic agents, it also causes some stimulation of the cardiocascular system. Ketamine has been reported to produce general as well as local anaesthesia. It interacts with N-methyl-D-aspartate (NMDA) receptors, opioid receptors, monoaminergic receptors, muscarinic receptors and voltage sensitive Ca ion channels. Unlike other general anaesthetic agents, ketamine does not interact with GABA receptors. |
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Metabolism | Hepatic.
Half Life: 2.5-3 hours. |
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Toxicity Values | Not Available |
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Lethal Dose | Not Available |
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Carcinogenicity (IARC Classification) | No indication of carcinogenicity to humans (not listed by IARC). |
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Uses/Sources | Ketamine is primarily used for the induction and maintenance of general anesthesia, usually in combination with some sedative drug. Other uses include sedation in intensive care, analgesia (particularly in emergency medicine), and treatment of bronchospasm. It is also a popular anesthetic in veterinary medicine. [Wikipedia] For use as the sole anesthetic agent for diagnostic and surgical procedures that do not require skeletal muscle relaxation. |
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Minimum Risk Level | Not Available |
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Health Effects | Chronic use of ketamine may lead to cognitive impairments including memory problems. [Wikipedia] |
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Symptoms | Ketamine has a wide range of effects in humans, including analgesia, anesthesia, hallucinations, elevated blood pressure, and bronchodilation.[Wikipedia] |
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Treatment | Supportive ventilation should be employed. Mechanical support of respiration is preferred to administration of analeptics. (7) |
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Normal Concentrations |
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| Not Available |
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Abnormal Concentrations |
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| Not Available |
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External Links |
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DrugBank ID | DB01221 |
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HMDB ID | HMDB15352 |
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PubChem Compound ID | 3821 |
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ChEMBL ID | CHEMBL742 |
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ChemSpider ID | 3689 |
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KEGG ID | C07525 |
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UniProt ID | Not Available |
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OMIM ID | |
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ChEBI ID | 6121 |
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BioCyc ID | Not Available |
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CTD ID | Not Available |
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Stitch ID | Ketamine |
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PDB ID | Not Available |
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ACToR ID | Not Available |
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Wikipedia Link | Ketamine |
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References |
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Synthesis Reference | John A. Flores, Kenton L. Crowley, “Process for the preparation of ketamine ointment.” U.S. Patent US5817699, issued June, 1995. |
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MSDS | Link |
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General References | - Harrison NL, Simmonds MA: Quantitative studies on some antagonists of N-methyl D-aspartate in slices of rat cerebral cortex. Br J Pharmacol. 1985 Feb;84(2):381-91. [2858237 ]
- Bergman SA: Ketamine: review of its pharmacology and its use in pediatric anesthesia. Anesth Prog. 1999 Winter;46(1):10-20. [10551055 ]
- Bonanno FG: Ketamine in war/tropical surgery (a final tribute to the racemic mixture). Injury. 2002 May;33(4):323-7. [12091028 ]
- Lankenau SE, Sanders B, Bloom JJ, Hathazi D, Alarcon E, Tortu S, Clatts MC: First injection of ketamine among young injection drug users (IDUs) in three U.S. cities. Drug Alcohol Depend. 2007 Mar 16;87(2-3):183-93. Epub 2006 Sep 18. [16979848 ]
- Reboso Morales JA, Gonzalez Miranda F: [Ketamine]. Rev Esp Anestesiol Reanim. 1999 Mar;46(3):111-22. [10228376 ]
- Drugs.com [Link]
- RxList: The Internet Drug Index (2009). [Link]
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Gene Regulation |
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Up-Regulated Genes | Not Available |
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Down-Regulated Genes | Gene | Gene Symbol | Gene ID | Interaction | Chromosome | Details |
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