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Ketamine
Also known as: 1867-66-9, Vetalar, Ketaset, Ketalar, Ketamine hcl, Ketanest
Molecular Formula
C13H17Cl2NO
Molecular Weight
274.18  g/mol
InChI Key
VCMGMSHEPQENPE-UHFFFAOYSA-N
FDA UNII
O18YUO0I83

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.
1 2D Structure

Ketamine

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
2-(2-chlorophenyl)-2-(methylamino)cyclohexan-1-one;hydrochloride
2.1.2 InChI
InChI=1S/C13H16ClNO.ClH/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;1H
2.1.3 InChI Key
VCMGMSHEPQENPE-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CNC1(CCCCC1=O)C2=CC=CC=C2Cl.Cl
2.2 Other Identifiers
2.2.1 UNII
O18YUO0I83
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 2-(2-chlorophenyl)-2-(methylamino)cyclohexanone

2. Calipsol

3. Calypsol

4. Ci 581

5. Ci-581

6. Ci581

7. Kalipsol

8. Ketalar

9. Ketamine

10. Ketanest

11. Ketaset

2.3.2 Depositor-Supplied Synonyms

1. 1867-66-9

2. Vetalar

3. Ketaset

4. Ketalar

5. Ketamine Hcl

6. Ketanest

7. Ketolar

8. 2-(2-chlorophenyl)-2-(methylamino)cyclohexanone Hydrochloride

9. Cl 369

10. Cn-52,372-2

11. (+-)-ketamine Hydrochloride

12. Ci-581

13. Ketamine Hydrochloride Ciii

14. Ketamine (as Hydrochloride)

15. O18yuo0i83

16. Calipsol

17. Kalipsol

18. Ketavet

19. (+-)-2-(o-chlorophenyl)-2-(methylamino)cyclohexanone Hydrochloride

20. Cl-369

21. Dea No. 7285

22. Cn-523722

23. 2-(2-chlorophenyl)-2-(methylamino)cyclohexan-1-one;hydrochloride

24. Cn-52372-2

25. Ketamine Chloride

26. Ketavet 100

27. Ketavet (veterinary)

28. Ci 581

29. Chebi:650657

30. Einecs 217-484-6

31. Unii-o18yuo0i83

32. Ketalar (tn)

33. Ketamini Hydrochloridum

34. Ketamine Hydrochloride [usan:usp:jan]

35. Cyclohexanone, 2-(2-chlorophenyl)-2-(methylamino)-, Hydrochloride

36. Cyclohexanone, 2-(2-chlorophenyl)-2-(methylamino)-, Hydrochloride, (+-)-

37. Ec 217-484-6

38. Chembl1714

39. Schembl26999

40. Dtxsid4040137

41. Ketamine Hydrochloride [mi]

42. 2-(2-chlorophenyl)-2-(methylamino)cyclohexan-1-one Hydrochloride

43. Bcp25943

44. Ketamine Hydrochloride (jp17/usp)

45. Ketamine Hydrochloride [jan]

46. (+/-)-2-(o-chlorophenyl)-2-(methylamino)cyclohexanone Hydrochloride

47. Ketamine Hydrochloride [usan]

48. Nsc116131

49. (+/-)-ketamine Hydrochloride, Solid

50. Ketamine Hydrochloride [vandf]

51. Akos005287313

52. Cyclohexanone, 2-(o-chlorophenyl)-2-(methylamino)-, Hydrochloride, (+-)-

53. Ketamine Hydrochloride [mart.]

54. Ab02117

55. Ketamine Hydrochloride [who-dd]

56. Ketamine Hydrochloride [who-ip]

57. Nsc-116131

58. Ketamine Hydrochloride [green Book]

59. Db-044614

60. Db-048467

61. Ketamine Hydrochloride [ep Impurity]

62. Ketamine Hydrochloride [orange Book]

63. Ketamine Hydrochloride [ep Monograph]

64. Ketamine Hydrochloride Ciii [usp-rs]

65. Ketamine Hydrochloride [usp Monograph]

66. Ketamini Hydrochloridum [who-ip Latin]

67. C07843

68. D00711

69. 867k669

70. A813079

71. Q-201266

72. Q27105184

73. Ketamine Hydrochloride 1.0 Mg/ml In Methanol (as Free Base)

74. 2-(2-chlorophenyl)-2-(methylamino)-1-cyclohexanone Hydrochloride

75. Ketamine Hydrochloride, European Pharmacopoeia (ep) Reference Standard

76. Cyclohexanone, 2-(2-chlorophenyl)-2-(methylamino)-, Hydrochloride (1:1)

77. Cyclohexanone, 2-(o-chlorophenyl)-2-(methylamino)-, Hydrochloride, (+/-)-

78. Ketamine (+-)-2-(o-chlorophenyl)-2-(methylamino)cyclohexanonehydrochloride

79. Ketamine Hydrochloride Solution, 1.0 Mg/ml In Methanol (as Free Base), Ampule Of 1 Ml, Certified Reference Material

2.4 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 274.18 g/mol
Molecular Formula C13H17Cl2NO
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count2
Rotatable Bond Count2
Exact Mass273.0687196 g/mol
Monoisotopic Mass273.0687196 g/mol
Topological Polar Surface Area29.1 Ų
Heavy Atom Count17
Formal Charge0
Complexity269
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count1
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count2
4 Drug and Medication Information
4.1 Drug Information
1 of 4  
Drug NameKetalar
Drug LabelKetalar is a nonbarbiturate anesthetic chemically designated dl 2-(0-chlorophenyl)-2-(methylamino) cyclohexanone hydrochloride. It is formulated as a slightly acid (pH 3.5-5.5) sterile solution for intravenous or intramuscular injection in concentrat...
Active IngredientKetamine hydrochloride
Dosage FormInjectable
RouteInjection
Strengtheq 10mg base/ml; eq 50mg base/ml; eq 100mg base/ml
Market StatusPrescription
CompanyPar Sterile Products

2 of 4  
Drug NameKetamine hydrochloride
PubMed HealthKetamine (Injection)
Drug LabelKetamine hydrochloride is a nonbarbiturate anesthetic chemically designated dl 2-(0-chlorophenyl)-2-(methylamino) cyclohexanone hydrochloride. It is formulated as a slightly acid (pH 3.5-5.5) sterile solution for intravenous or intramuscular injectio...
Active IngredientKetamine hydrochloride
Dosage FormInjectable
RouteInjection
Strengtheq 10mg base/ml; eq 50mg base/ml; eq 100mg base/ml
Market StatusPrescription
CompanyHospira; Mylan Institutional; Eurohlth Intl

3 of 4  
Drug NameKetalar
Drug LabelKetalar is a nonbarbiturate anesthetic chemically designated dl 2-(0-chlorophenyl)-2-(methylamino) cyclohexanone hydrochloride. It is formulated as a slightly acid (pH 3.5-5.5) sterile solution for intravenous or intramuscular injection in concentrat...
Active IngredientKetamine hydrochloride
Dosage FormInjectable
RouteInjection
Strengtheq 10mg base/ml; eq 50mg base/ml; eq 100mg base/ml
Market StatusPrescription
CompanyPar Sterile Products

4 of 4  
Drug NameKetamine hydrochloride
PubMed HealthKetamine (Injection)
Drug LabelKetamine hydrochloride is a nonbarbiturate anesthetic chemically designated dl 2-(0-chlorophenyl)-2-(methylamino) cyclohexanone hydrochloride. It is formulated as a slightly acid (pH 3.5-5.5) sterile solution for intravenous or intramuscular injectio...
Active IngredientKetamine hydrochloride
Dosage FormInjectable
RouteInjection
Strengtheq 10mg base/ml; eq 50mg base/ml; eq 100mg base/ml
Market StatusPrescription
CompanyHospira; Mylan Institutional; Eurohlth Intl

5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Anesthetics, Dissociative

Intravenous anesthetics that induce a state of sedation, immobility, amnesia, and marked analgesia. Subjects may experience a strong feeling of dissociation from the environment. The condition produced is similar to NEUROLEPTANALGESIA, but is brought about by the administration of a single drug. (From Gilman et al., Goodman and Gilman's The Pharmacological Basis of Therapeutics, 8th ed) (See all compounds classified as Anesthetics, Dissociative.)


Analgesics

Compounds capable of relieving pain without the loss of CONSCIOUSNESS. (See all compounds classified as Analgesics.)


Excitatory Amino Acid Antagonists

Drugs that bind to but do not activate excitatory amino acid receptors, thereby blocking the actions of agonists. (See all compounds classified as Excitatory Amino Acid Antagonists.)


5.2 FDA Pharmacological Classification
5.2.1 Pharmacological Classes
General Anesthetic [EPC]; General Anesthesia [PE]
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  • INJECTABLE;INJECTION - EQ 100MG BASE/ML
  • INJECTABLE;INJECTION - EQ 10MG BASE/ML
  • INJECTABLE;INJECTION - EQ 50MG BASE/ML
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