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    2-(2-Chlorophenyl)-2-(methylamino)cyclohexanone

    ACTIVE PHARMA INGREDIENTS

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    2D Structure
    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

    2D Structure

    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]