Introduction：Basic information about KETAMINE HYDROCHLORIDE SELECTIVE NMDA AN TAGO CAS 6740-88-1, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
KETAMINE HYDROCHLORIDE SELECTIVE NMDA AN TAGO Basic information
| Product Name: | KETAMINE HYDROCHLORIDE SELECTIVE NMDA AN TAGO |
| Synonyms: | 2-(2-chlorophenyl)-2-methylamino-cyclohexan-1-one;Cyclohexanone, 2-(2-chlorophenyl)-2-(methylamino)-;(±)-2-(o-Chlorophenyl)-2-(methylamino)cyclohexanone;Cyclohexanone, 2-(2-chlorophenyl)-2-(methylamino)- (9CI);Cyclohexanone, 2-(o-chlorophenyl)-2-(methylamino)-, (±)- (8CI);dl-Ketamine;Ketoject;NSC 70151 |
| CAS: | 6740-88-1 |
| MF: | C13H16ClNO |
| MW: | 237.73 |
| EINECS: | 229-804-1 |
| Product Categories: | |
| Mol File: | 6740-88-1.mol |
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KETAMINE HYDROCHLORIDE SELECTIVE NMDA AN TAGO Chemical Properties
| Melting point | 92-93° |
| Boiling point | 363.8±42.0 °C(Predicted) |
| density | 1.0982 (rough estimate) |
| refractive index | 1.6330 (estimate) |
| pka | 7.5(at 25℃) |
| EPA Substance Registry System | Cyclohexanone, 2-(2-chlorophenyl)-2-(methylamino)- (6740-88-1) |
Safety Information
| RIDADR | 3249 |
| HazardClass | 6.1(b) |
| PackingGroup | III |
| Hazardous Substances Data | 6740-88-1(Hazardous Substances Data) |
KETAMINE HYDROCHLORIDE SELECTIVE NMDA AN TAGO Usage And Synthesis
| Originator | Ketanest,Parke Davis,W. Germany,1969 |
| Uses | Anesthetic. |
| Definition | ChEBI: Ketamine is a member of the class of cyclohexanones in which one of the hydrogens at position 2 is substituted by a 2-chlorophenyl group, while the other is substituted by a methylamino group. It has a role as an intravenous anaesthetic, a NMDA receptor antagonist, an analgesic, a neurotoxin, an environmental contaminant and a xenobiotic. It is a member of cyclohexanones, a secondary amino compound and a member of monochlorobenzenes. |
| Manufacturing Process | The 1-hydroxycyclopentyl-(o-chlorophenyl)-ketone N-methylimine used as anintermediate is prepared as follows. To the Grignard reagent prepared from119.0 g of cyclopentyl bromide and 19.4 g of magnesium is added 55.2 g ofo-chlorobenzonitrile. The reaction mixture is stirred for 3 days and thereafterhydrolyzed in the usual manner. From the hydrolysis there is obtained ochlorophenylcyclopentylketone, BP 96° to 97°C (0.3 mm), nD251.5452. To21.0 g of the ketone is added 10.0 g of bromine in 80 ml of carbontetrachloride.
1-Bromocyclopentyl-(o-chlorophenyl)-ketone, BP 111° to 114°C (0.1 mm) isisolated in the usual manner. Since it is unstable, it must be usedimmediately. The bromoketone (29.0 g) is dissolved in 50 ml of liquidmethylamine. After one hour, the excess liquid methylamine is allowed toevaporate. The organic residue is dissolved in pentane, and upon evaporationof the solvent, 1-hydroxycyclopentyl-(o-chlorophenyl)-ketone N-methylimine,MP 62°C, is isolated.
1-Hydroxycyclopentyl-(o-chlorophenyl)-ketone N-methylimine (2.0 g) isdissolved in 15 ml of Decalin and refluxed for 2,5 hours. After evaporation ofthe Decalin under reduced pressure, the residue is extracted with dilutehydrochloric acid, the solution treated with decolorizing charcoal, and theresulting acidic solution is made basic. The liberated product, 2-methylamino-2-(o-chlorophenyl)-cyclohexanone, after crystallization from pentane-ether,has MP 92° to 93°C. The hydrochloride of this compound has MP 262° to263°C. |
| Brand name | Ketalar (Parkdale). |
| Therapeutic Function | Anesthetic |
| Mechanism of action | The mode of action of ketamine differs fromthat of the barbiturates. It suppresses the activitiesof the cerebral cortex (consciousness) andthe thalamic pain pathways (analgesia). Partsof the upper brainstem and the limbic systemare not affected (so-called dissociative analgesia).The patient exhibits a characteristic superficialsleep with complete elimination of pain.Because of the psychomotor side effects, combinationwith neuroleptics and tranquilizers isnecessary. Ketamine is used especially in pediatrics.The usual preparations are 0.1 % and0.5 % solutions. |
| Clinical Use | Ketamine is a short-acting anesthetic effectivefor 5 – 30 min, depending on the amount injected.It is suitable for diagnostic purposes andfor surgical procedures that do not require musclerelaxation. The occasional hallucinationsthat occur during anesthesia suggest a chemicalrelationship to phencyclidine, which was usedas a short-acting anesthetic until identified as adangerous drug of abuse. |
| Synthesis | It is prepared by bromination of o-chlorophenylcyclopentyl ketone, which is then reactedwith methylamine to give the methylimino alcohol.Thermolysis of the imino hydrochlorideyields ketamine by ring expansion :
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KETAMINE HYDROCHLORIDE SELECTIVE NMDA AN TAGO Preparation Products And Raw materials
| Raw materials | Methylamine-->Magnesium-->Bromocyclopentane-->2-Chlorobenzonitrile |
| Preparation Products | (S)-(+)-Ketamine hydrochloride |
