{"ATC Code":"N01AX03","Abbreviation":["2-Cl-2'-Oxo-PCM","K"],"Adverse Effects":"The most common adverse drug reactions associated with ketamine are nausea, vomiting, dizziness, diplopia, drowsiness, dysphoria, and confusion. Reports of the emergence phenomenon exist for approximately 6% to 12% of patients. The common adverse drug reactions of ketamine are listed below.","Aliases":["Ketamine","ketamine","Ketaject","Special K","CI 581 base","Ketaminum","CLSTA 20","Calypsol","narketan","Cetamina","Tekam","ketamina","2-(Methylamino)-2-(2-chlorophenyl)cyclohexanone","Ursotamin","Vetaket","Anaket v","2-(o-Chlorophenyl)-2-(methylamino)-cyclohexanone","Clorketam 1000","Ketasol 100","2-(2-Chlorophenyl)-2-(methylamino)cyclohexanone","Imalgene 1000","cyclohexanone, 2-(2-chlorophenyl)-2-(methylamino)-","PMI-150","Cyclohexanone, 2-(o-chlorophenyl)-2-(methylamino)-, (+-)-","Ketafol component ketamine"],"Biological Half-Life":"The reported half-life in preclinical studies for ketamine is 186 min.","CAS":"6740-88-1","ChEBI":"CHEBI:6121","ChEMBL":"CHEMBL742","ChemicalClasses":["arylcyclohexylamine"],"Chirality":"racemic","Color/Form":"Crystals from pentane-ether","DEA no":7285,"Decomposition":"When heated to decomposition it emits toxic fumes of /chloride/ and /nitrogen oxides/.","Drug Classes":"Breast Feeding; Lactation; Milk, Human; Anesthetics, Intravenous; Hypnotics and Sedatives; Anesthetics, Dissociative; Excitatory Amino Acid Antagonists","Drug Indication":"Ketamine is indicated as an anesthetic agent for recommended diagnostic and surgical procedures. If skeletal muscle relaxation is needed, it should be combined with a muscle relaxant. If the surgical procedure involves visceral pain, it should be supplemented with an agent that obtunds visceral pain. Ketamine can be used for induction of anesthesia prior other general anesthetic agents and as a supplement of low potency agents.  Reports have indicated a potential use of ketamine as a therapeutic tool for the management of depression when administered in lower doses. These reports have increased the interest for ketamine in this area and several clinical trials are launched for this indication.","Drug Warnings":"Special note: Emergence reactions have occurred in approximately 12 percent of patients. The psychological manifestations vary in severity between pleasant dream-like states, vivid imagery, hallucinations, and emergence delirium. In some cases these states have been accompanied by confusion, excitement, and irrational behavior which a few patients recall as an unpleasant experience. The duration ordinarily is no more than a few hours; in a few cases, however, recurrences have taken place up to 24 hours postoperatively. No residual psychological effects are known to have resulted from use of ketamine. The incidence of these emergence phenomena is least in the young (15 years of age or less) and elderly (over 65 years of age) patient. Also, they are less frequent when the drug is given intramuscularly and the incidence is reduced as experience with the drug is gained. The incidence of psychological manifestations during emergence, particularly dream-like observations and emergence delirium, may be reduced by using lower recommended dosages of ketamine in conjunction with intravenous diazepam during induction and maintenance of anesthesia. ... Also, these reactions may be reduced if verbal, tactile and visual stimulation of the patient is minimized during the recovery period. This does not preclude the monitoring of vital signs. In order to terminate a severe emergence reaction, the use of a small hypnotic dose of a short-acting or ultra short-acting barbiturate may be required. When ketamine is used on an outpatient basis, the patient should not be released until recovery from anesthesia is complete and then should be accompanied by a responsible adult.","DurationOfAction":"* Intramuscular: 0.5 – 2 hours\n* Insufflation: 45 – 60 min\n* By mouth: 1 – 6+ hours","EINECS":"229-804-1","EliminationHalfLife":"* Ketamine: 2.5 – 3 hours\n* Norketamine: 12 hours","Esters":[],"European Community (EC) Number":"229-804-1","FDA Pharmacological Classification":"690G0D6V8H","Formating":[],"HMDB ID":"HMDB0015352","Health Effects":"Chronic use of ketamine may lead to cognitive impairments including memory problems. [Wikipedia]","HeavyAtomCount":16,"Human Drugs":"Breast Feeding; Lactation; Milk, Human; Anesthetics, Intravenous; Hypnotics and Sedatives; Anesthetics, Dissociative; Excitatory Amino Acid Antagonists","IUPACName":"2-(2-chlorophenyl)-2-(methylamino)cyclohexan-1-one","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","InChIKey":"YQEZLKZALYSWHR-UHFFFAOYSA-N","Interactions":"/The study objective was/ to determine the effects of ketamine-diazepam and ketamine-acepromazine combinations on intraocular pressure (IOP) in rabbits. /This was a/ randomized clinical trial. Sixteen adult New Zealand white rabbits approximately one year old, weighing 2.3 +/- 0.2 kg were used in this study. The animals were randomly divided into two groups of eight each (KA and KD). The pre-treatment IOPs were recorded in both groups (T0). All rabbits in group KA received intramuscular ketamine-acepromazine (ketamine 30 mg/kg + acepromazine 0.5 mg/kg). Ketamine-diazepam (ketamine 30 mg/kg + diazepam 1 mg/kg) was administered intramuscularly in members of group KD. The IOP values were measured at 5 (T(5)), 15 (T(15)), and 20 (T(20)) minutes after drug administration in both treatment groups. Significant increases in IOP values were observed in both treatment groups at T(5,) T(15), and T(20) in comparison to the baseline values. In group KA the mean +/- SD IOP at T(5,) T(15), and T(20) were 37 +/- 13 (p \u003c 0.001), 35 +/- 4 (p \u003c 0.001) and 34 +/- 4 mmHg (p \u003c 0.001). The post-treatment mean +/- sd values in group KD were 23 +/- 8 (p = 0.002), 23 +/- 5 (p \u003c 0.001) and 23 +/- 6 mmHg (p = 0.001) at 5, 15, and 20 minutes respectively. Both ketamine-diazepam and ketamine-acepromazine combinations increased IOP after intramuscular administration in rabbits.","LD50":[{"dosages":[{"amount":"77 mg/kg","route":"intravenous"},{"amount":"400 mg/kg","route":"intraperitoneal"}],"organism":"Mouse"}],"MeSH Pharmacological Classification":"Compounds capable of relieving pain without the loss of CONSCIOUSNESS.","Melting Point":"92.5ºC","MolecularFormula":"C\u003csub\u003e13\u003c/sub\u003eH\u003csub\u003e16\u003c/sub\u003eClNO","MolecularWeight":"237.72 g/mol","Non-Human Toxicity Values":"LD50 Mouse ip 400 mg/kg","Opticalactivity":"( + / - )","Pharmacodynamics":"Ketamine is a rapid-acting general anesthetic producing an anesthetic state characterized by profound analgesia, normal pharyngeal-laryngeal reflexes, normal or slightly enhanced skeletal muscle tone, cardiovascular and respiratory stimulation, and occasionally a transient and minimal respiratory depression. The anesthetic state produced by Ketamine has been termed as \"dissociative anesthesia\" in that it appears to selectively interrupt association pathways of the brain before producing somesthetic sensory blockade. It may selectively depress the thalamoneocortical system before significantly obtunding the more ancient cerebral centers and pathways (reticular-activating and limbic systems).  Ketamine enhances descending inhibiting serotoninergic pathways and can exert antidepressive effects. These effects are seen in concentrations ten times lower than the needed concentration for anesthetic proposes. The effect of ketamine can be described as analgesic by the prevention of central sensitization in dorsal horn neurons as well as by the inhibition on the synthesis of nitric oxide. Ketamine can present cardiovascular changes and bronchodilatation.","Physical Description":"Solid","PubChemId":3821,"Record Description":["LiverTox|CNS|Anesthetic|NMDA receptor antagonist"],"RefCount":3,"RefCur":"","References":[{"Name":"Wikipedia","Urls":[{"Link":"https://en.wikipedia.org/wiki/Ketamine","Name":"Ketamine","Sub":false},{"Link":"https://en.wikipedia.org/wiki/Arketamine","Name":"Esketamine","Sub":true},{"Link":"https://en.wikipedia.org/wiki/Esketamine","Name":"Esketamine","Sub":true}]},{"Name":"Wikidata","Urls":[{"Link":"https://www.wikidata.org/wiki/Q243547","Name":"Ketamine","Sub":false},{"Link":"https://www.wikidata.org/wiki/Q20707684","Name":"Esketamine","Sub":true},{"Link":"https://www.wikidata.org/wiki/Q2365493","Name":"Esketamine","Sub":true}]},{"Name":"DrugBank","Urls":[{"Link":"https://go.drugbank.com/drugs/DB01221","Name":"Ketamine","Sub":false},{"Link":"https://go.drugbank.com/drugs/DB19150","Name":"Esketamine","Sub":true},{"Link":"https://go.drugbank.com/drugs/DB11823","Name":"Esketamine","Sub":true}]},{"Name":"PubChem","Urls":[{"Link":"https://pubchem.ncbi.nlm.nih.gov/compound/3821","Name":"Ketamine","Sub":false},{"Link":"https://pubchem.ncbi.nlm.nih.gov/compound/644025","Name":"Esketamine","Sub":true},{"Link":"https://pubchem.ncbi.nlm.nih.gov/compound/182137","Name":"Esketamine","Sub":true}]},{"Name":"ChEMBL","Urls":[{"Link":"https://www.ebi.ac.uk/chembl/explore/compound/CHEMBL742","Name":"Ketamine","Sub":false},{"Link":"https://www.ebi.ac.uk/chembl/explore/compound/CHEMBL467505","Name":"Esketamine","Sub":true},{"Link":"https://www.ebi.ac.uk/chembl/explore/compound/CHEMBL395091","Name":"Esketamine","Sub":true}]},{"Name":"ChEBI","Urls":[{"Link":"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:6121","Name":"Ketamine","Sub":false},{"Link":"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:580604","Name":"Esketamine","Sub":true},{"Link":"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:60799","Name":"Esketamine","Sub":true}]},{"Name":"Common Chemistry","Urls":[{"Link":"https://commonchemistry.cas.org/detail?cas_rn=6740-88-1","Name":"Ketamine","Sub":false},{"Link":"https://commonchemistry.cas.org/detail?cas_rn=33643-49-1","Name":"Esketamine","Sub":true},{"Link":"https://commonchemistry.cas.org/detail?cas_rn=33643-46-8","Name":"Esketamine","Sub":true}]},{"Name":"HMDB","Urls":[{"Link":"https://hmdb.ca/metabolites/HMDB0015352","Name":"Ketamine","Sub":false}]},{"Name":"KEGG","Urls":[{"Link":"https://www.kegg.jp/entry/C07525","Name":"Ketamine","Sub":false},{"Link":"https://www.kegg.jp/entry/D07283","Name":"Esketamine","Sub":true}]},{"Name":"UNII","Urls":[{"Link":"https://gsrs.ncats.nih.gov/ginas/app/ui/substances/690G0D6V8H","Name":"Ketamine","Sub":false},{"Link":"https://gsrs.ncats.nih.gov/ginas/app/ui/substances/Y2RI13H7VW","Name":"Esketamine","Sub":true},{"Link":"https://gsrs.ncats.nih.gov/ginas/app/ui/substances/50LFG02TXD","Name":"Esketamine","Sub":true}]},{"Name":"EPA DSSTox","Urls":[{"Link":"https://comptox.epa.gov/dashboard/chemical/details/DTXSID8023187","Name":"Ketamine","Sub":false},{"Link":"https://comptox.epa.gov/dashboard/chemical/details/DTXSID2048747","Name":"Esketamine","Sub":true},{"Link":"https://comptox.epa.gov/dashboard/chemical/details/DTXSID6047810","Name":"Esketamine","Sub":true}]}],"Refs":["National Center for Biotechnology Information. PubChem Compound Summary for CID 3821, Ketamine. Accessed September 6, 2025. \u003ca href=https://pubchem.ncbi.nlm.nih.gov/compound/3821\u003ehttps://pubchem.ncbi.nlm.nih.gov/compound/3821\u003c/a\u003e","U.S. Food and Drug Administration; National Center for Advancing Translational Sciences. Ketamine. UNII: 690G0D6V8H. Global Substance Registration System. Accessed September 6, 2025. \u003ca href=https://gsrs.ncats.nih.gov/ginas/app/beta/substances/690G0D6V8H\u003ehttps://gsrs.ncats.nih.gov/ginas/app/beta/substances/690G0D6V8H\u003c/a\u003e"],"SMILES":"CNC1(CCCCC1=O)C2=CC=CC=C2Cl","SaltData":[{"AcidCount":1,"Amine":"Ketamine","AmineCount":1,"Formula":"Cl","Name":"hydrochloride","Structure":"\u003csvg xmlns=\"http://www.w3.org/2000/svg\" preserveAspectRatio=\"none\" style=\"display:block\" viewBox=\"0 0 87.861 70.208\"\u003e\u003crect width=\"100%\" height=\"100%\" fill=\"#fff\"/\u003e\u003cdesc\u003eGenerated by the Chemistry Development Kit (http://github.com/cdk)\u003c/desc\u003e\u003cg fill=\"#1ff01f\" stroke=\"#000\" stroke-linecap=\"round\" stroke-linejoin=\"round\" stroke-width=\".7\"\u003e\u003cpath fill=\"#fff\" stroke=\"none\" d=\"M0 0h88v71H0z\"/\u003e\u003cg class=\"mol\"\u003e\u003cpath d=\"m40.317 12.677 3.843 10.555M42.69 30.383l-6.954 8.29M35.736 38.673l-13.203 7.628M22.533 46.301l-.005 15.249M22.528 61.55l13.198 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class=\"hi\"/\u003e\u003c/g\u003e\u003c/g\u003e\u003c/svg\u003e","Title":"Esketamine","UNII":"Y2RI13H7VW"},{"Aliases":["Esketamine","l-Ketamine","(S)-Ketamine","S-Ketamine","(S)-(-)-Ketamine","Ketaved","Keta-s","Ketamine, s-","Ketamine, (s)-","S-(-)-Ketamine","esketamina","Kataved","(S)-2-(o-chlorophenyl)-2-(methylamino)cyclohexanone","Jnj-54135419","(2S)-2-(2-chlorophenyl)-2-(methylamino)cyclohexanone","cyclohexanone, 2-(2-chlorophenyl)-2-(methylamino)-, (2S)-","(2S)-2-(2-chlorophenyl)-2-methylaminocyclohexan-1-one","esketaminum","RefChem:56383","N01AX14","N06AX27","(2~{S})-2-(2-chlorophenyl)-2-(methylamino)cyclohexan-1-one","Cyclohexanone, 2-(2-chlorophenyl)-2-(methylamino)-, (S)-","S-Ketamin","JC9"],"PubChemId":182137,"SMILES":"CN[C@@]1(CCCCC1=O)C2=CC=CC=C2Cl","Structure":"\u003csvg xmlns=\"http://www.w3.org/2000/svg\" preserveAspectRatio=\"none\" style=\"display:block\" viewBox=\"0 0 64.953 70.208\"\u003e\u003crect width=\"100%\" height=\"100%\" 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1.28-.322.78 0 1.351.286l-.244.524q-.226-.101-.506-.185-.274-.083-.607-.083m2.757 4.423h-.602v-5.215h.602z\" class=\"atom\"/\u003e\u003cpath stroke=\"#3050f8\" d=\"m44.16 23.232-1.921-5.278M42.69 30.383l-3.477 4.145\" class=\"hi\"/\u003e\u003cpath stroke=\"#1ff01f\" d=\"m6.589 41.839 2.185-6.095\" class=\"hi\"/\u003e\u003c/g\u003e\u003c/g\u003e\u003c/svg\u003e","Therapeutic Uses":"Analgesics; Anesthetics, Dissociative; Excitatory Amino Acid Antagonists","Title":"Ketamine","Treatment":"Supportive ventilation should be employed. Mechanical support of respiration is preferred to administration of analeptics. (L1712)","UNII":"690G0D6V8H","Wikidata":"Q243547","Wikipedia":"Ketamine","XLogP":2.2,"pH":"pH of 10% aqueous solution: 3.5"}