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    Normethadone

    ACTIVE PHARMA INGREDIENTS

    INTERMEDIATES

    PharmaCompass
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    2D Structure
    Also known as: Mepidon, Isomethadone i, Phenyldimazone, Eucopon, Desmethylmethadone, Noramidone
    Molecular Formula
    C20H25NO
    Molecular Weight
    295.4  g/mol
    InChI Key
    WCJFBSYALHQBSK-UHFFFAOYSA-N
    FDA UNII
    KR2L2A68XL
    Normethadone is used as an opioid antitussive in combination with [DB11610]. It is marketed in Canada by Valeant under the tradename Cophylac.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    6-(dimethylamino)-4,4-diphenylhexan-3-one
    2.1.2 InChI
    InChI=1S/C20H25NO/c1-4-19(22)20(15-16-21(2)3,17-11-7-5-8-12-17)18-13-9-6-10-14-18/h5-14H,4,15-16H2,1-3H3
    2.1.3 InChI Key
    WCJFBSYALHQBSK-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CCC(=O)C(CCN(C)C)(C1=CC=CC=C1)C2=CC=CC=C2
    2.2 Other Identifiers
    2.2.1 UNII
    KR2L2A68XL
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 6-dimethylamino-4,4-diphenylhexan-3-one

    2. Nor-methadone

    3. Normethadone Hydrochloride

    2.3.2 Depositor-Supplied Synonyms

    1. Mepidon

    2. Isomethadone I

    3. Phenyldimazone

    4. Eucopon

    5. Desmethylmethadone

    6. Noramidone

    7. Normedon

    8. Dacartil

    9. Hoechst 10582

    10. Isoamidone I

    11. 467-85-6

    12. 6-dimethylamino-4,4-diphenyl-3-hexanone

    13. Nsc 19598

    14. Nsc-19598

    15. Kr2l2a68xl

    16. 3-hexanone, 6-(dimethylamino)-4,4-diphenyl-

    17. Hoechst-10582

    18. Ids-nn-007

    19. Normethadone (inn)

    20. J5.915c

    21. Normethadone [inn]

    22. Normetadone [dcit]

    23. Normetadona

    24. Normetadone

    25. Normethadonum

    26. Normetadona [inn-spanish]

    27. Normethadonum [inn-latin]

    28. Normethadone [inn:ban:dcf]

    29. 6-(dimethylamino)-4,4-diphenylhexan-3-one

    30. Einecs 207-401-1

    31. Unii-kr2l2a68xl

    32. Brn 2748978

    33. 6-dimethylamino-4,4-diphenyl-3-hexanon

    34. Normethadon

    35. 1-dimethylamino-3,3-diphenyl-4-hexanone

    36. Ai3-23988

    37. Dea No. 9635

    38. Nonmethadone

    39. 3-hexanone,4-diphenyl-

    40. Normethadone [mi]

    41. Dsstox_cid_31537

    42. Dsstox_rid_97422

    43. Dsstox_gsid_57748

    44. Schembl24337

    45. 4-14-00-00297 (beilstein Handbook Reference)

    46. Normethadone [who-dd]

    47. Chembl346331

    48. 467-85-6 (free Base)

    49. Dtxsid6057748

    50. Chebi:135242

    51. Wln: 2vxr&r&2n1&1

    52. Nsc19598

    53. Zinc1847280

    54. Tox21_113687

    55. 6-dimethylamio-4-diphenyl-3-hexanone

    56. Db11609

    57. Ncgc00249911-01

    58. Cas-467-85-6

    59. D07384

    60. Q1218578

    61. 1,1-diphenyl-1-(2-dimethylaminoethyl)-2-butanone

    2.4 Create Date
    2005-03-26
    3 Chemical and Physical Properties
    Molecular Weight 295.4 g/mol
    Molecular Formula C20H25NO
    XLogP33.5
    Hydrogen Bond Donor Count0
    Hydrogen Bond Acceptor Count2
    Rotatable Bond Count7
    Exact Mass295.193614421 g/mol
    Monoisotopic Mass295.193614421 g/mol
    Topological Polar Surface Area20.3 Ų
    Heavy Atom Count22
    Formal Charge0
    Complexity320
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Indication

    For use in the treatment of cough when other less potent treatments have failed.

    FDA Label

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Normethadone is an opioid which suppresses coughing by central and peripheral mechanisms.

    5.2 MeSH Pharmacological Classification

    Analgesics, Opioid

    Compounds with activity like OPIATE ALKALOIDS, acting at OPIOID RECEPTORS. Properties include induction of ANALGESIA or NARCOSIS. (See all compounds classified as Analgesics, Opioid.)

    Antitussive Agents

    Agents that suppress cough. They act centrally on the medullary cough center. EXPECTORANTS, also used in the treatment of cough, act locally. (See all compounds classified as Antitussive Agents.)

    5.3 ATC Code

    R - Respiratory system

    R05 - Cough and cold preparations

    R05D - Cough suppressants, excl. combinations with expectorants

    R05DA - Opium alkaloids and derivatives

    R05DA06 - Normethadone

    5.4 Mechanism of Action

    Normethadone activates central opioid receptors in the medulla to supress the cough reflex. It also likely activates peripheral opioid receptors to inhibit signalling by irritant receptors of the airway.