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ACTIVE PHARMA INGREDIENTS

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Synopsis

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Chemistry

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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

Normethadone

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 Formula	C₂₀H₂₅NO
Molecular Weight	295.4 g/mol
XLogP3	3.5
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	7
Exact Mass	295.193614421 g/mol
Monoisotopic Mass	295.193614421 g/mol
Topological Polar Surface Area	20.3 Å²
Heavy Atom Count	22
Formal Charge	0
Complexity	320
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

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.

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