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Also known as: Dextromethorphan hydrobromide, 125-69-9, Antussan, Demorphan, Dormethan, Metrorat
Molecular Formula
C18H26BrNO
Molecular Weight
352.3  g/mol
InChI Key
MISZALMBODQYFT-URVXVIKDSA-N
FDA UNII
Z0CG3115FG

Dextromethorphan Hydrobromide
Methyl analog of DEXTRORPHAN that shows high affinity binding to several regions of the brain, including the medullary cough center. This compound is an NMDA receptor antagonist (RECEPTORS, N-METHYL-D-ASPARTATE) and acts as a non-competitive channel blocker. It is one of the widely used ANTITUSSIVES, and is also used to study the involvement of glutamate receptors in neurotoxicity.
1 2D Structure

Dextromethorphan Hydrobromide

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(1S,9S,10S)-4-methoxy-17-methyl-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5-triene;hydrobromide
2.1.2 InChI
InChI=1S/C18H25NO.BrH/c1-19-10-9-18-8-4-3-5-15(18)17(19)11-13-6-7-14(20-2)12-16(13)18;/h6-7,12,15,17H,3-5,8-11H2,1-2H3;1H/t15-,17+,18+;/m1./s1
2.1.3 InChI Key
MISZALMBODQYFT-URVXVIKDSA-N
2.1.4 Canonical SMILES
CN1CCC23CCCCC2C1CC4=C3C=C(C=C4)OC.Br
2.1.5 Isomeric SMILES
CN1CC[C@@]23CCCC[C@@H]2[C@@H]1CC4=C3C=C(C=C4)OC.Br
2.2 Other Identifiers
2.2.1 UNII
Z0CG3115FG
2.3 Synonyms
2.3.1 MeSH Synonyms

1. D-methorphan

2. Dextromethorphan

3. Dextromethorphan Hydrobromide

4. Dextromethorphan Hydrobromide, (+-)-isomer

5. Dextromethorphan Hydrobromide, Monohydrate

6. Dextromethorphan Hydrochloride

7. Dextromethorphan, (+-)-isomer

8. Hydrobromide, Dextromethorphan

9. Hydrochloride, Dextromethorphan

10. L-methorphan

11. Levomethorphan

12. Racemethorphan

2.3.2 Depositor-Supplied Synonyms

1. Dextromethorphan Hydrobromide

2. 125-69-9

3. Antussan

4. Demorphan

5. Dormethan

6. Metrorat

7. Medicon

8. Tusilan

9. Tussade

10. D-methorphan Hydrobromide

11. Romilar

12. Methorate Hydrobromide

13. Dextromethorphan Bromide

14. Dextromethorphan (hydrobromide)

15. Dextromethorphan Hydrobromide Anhydrous

16. Ro 1-5470/5

17. Dextromethorphan Hbr

18. D-3-methoxy-n-methylmorphinan Hydrobromide

19. Z0cg3115fg

20. Benylin Dm

21. (1s,9s,10s)-4-methoxy-17-methyl-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5-triene;hydrobromide

22. Romilar Hydrobromide

23. (9?,13?,14?)-3-methoxy-17-methylmorphinan Hydrobromide

24. Dextroramin P

25. Demorphine

26. Dextrometorphan Hydrobromide

27. Allfen-dm

28. (1s,9s,10r)-4-methoxy-17-methyl-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5-triene;hydrobromide

29. Nsc-756723

30. Demorphan Hydrobromide

31. Einecs 204-750-1

32. Dextromethorphan Polistirex

33. (9alpha,13alpha,14alpha)-3-methoxy-17-methylmorphinan Hydrobromide

34. Unii-z0cg3115fg

35. Canfodion

36. Cosylan

37. Dormetan

38. Hihustan M.

39. Ro 1-5470

40. Dxm Hbr

41. 9-alpha,13-alpha,14-alpha-morphinan, 3-methoxy-17-methyl-, Hydrobromide

42. Schembl121924

43. Morphinan, 3-methoxy-n-methyl-, Hydrobromide, (+)-

44. Chembl1201004

45. Dtxsid60872346

46. Bcp06595

47. Hy-b0620

48. Dextromethorphan Hbr Anhydrous

49. Mfcd00269810

50. Akos022186323

51. Ccg-212567

52. Nsc 756723

53. Dextromethorphan Hydrobromide [mi]

54. Dextromethorphan Hydrobromide [who-dd]

55. Q27294835

56. (9alpha,13alpha,14alpha)-3-methoxy-17-methylmorphinan Hbr

57. 3-methoxy-17-methyl-9.alpha.,13.alpha.,14.alpha.-morphinan Hbr

58. Morphinan, 3-methoxy-17-methyl-, (9alpha,13alpha,14alpha)-, Hydrobromide

59. 3-methoxy-17-methyl-9.alpha.,13.alpha.,14.alpha.-morphinan Hydrobromide

60. 9alpha,13alpha,14alpha-morphinan, 3-methoxy-17-methyl-, Hydrobromide (8ci)

61. Morphinan, 3-methoxy-17-methyl-, (9.alpha.,13.alpha.,14.alpha.)-, Hbr

62. Morphinan, 3-methoxy-17-methyl-, (9.alpha.,13.alpha.,14.alpha.)-, Hydrobromide

63. Morphinan, 3-methoxy-17-methyl-, Hydrobromide (1:1),(9.alpha.,13.alpha.,14.alpha.)-

64. (4bs,8as,9s)-3-methoxy-11-methyl-6,7,8,8a,9,10-hexahydro-5h-9,4b-(epiminoethano)phenanthrene Hydrobromide

65. 1887136-04-0

2.4 Create Date
2005-06-08
3 Chemical and Physical Properties
Molecular Weight 352.3 g/mol
Molecular Formula C18H26BrNO
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count2
Rotatable Bond Count1
Exact Mass351.11978 g/mol
Monoisotopic Mass351.11978 g/mol
Topological Polar Surface Area12.5 Ų
Heavy Atom Count21
Formal Charge0
Complexity370
Isotope Atom Count0
Defined Atom Stereocenter Count3
Undefined Atom Stereocenter Count0
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 NameDelsym
Active IngredientDextromethorphan polistirex
Dosage FormSuspension, extended release
RouteOral
Strengtheq 30mg hbr/5ml
Market StatusOver the Counter
CompanyReckitt Benckiser

2 of 4  
Drug NameDextromethorphan polistirex
Active IngredientDextromethorphan polistirex
Dosage FormSuspension, extended release
RouteOral
Strengtheq 30mg hbr/5ml
Market StatusOver the Counter
CompanyTris Pharma

3 of 4  
Drug NameDelsym
Active IngredientDextromethorphan polistirex
Dosage FormSuspension, extended release
RouteOral
Strengtheq 30mg hbr/5ml
Market StatusOver the Counter
CompanyReckitt Benckiser

4 of 4  
Drug NameDextromethorphan polistirex
Active IngredientDextromethorphan polistirex
Dosage FormSuspension, extended release
RouteOral
Strengtheq 30mg hbr/5ml
Market StatusOver the Counter
CompanyTris Pharma

5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

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.)


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.)


5.2 FDA Pharmacological Classification
5.2.1 Pharmacological Classes
Sigma-1 Receptor Agonists [MoA]; Uncompetitive N-methyl-D-aspartate Receptor Antagonist [EPC]; Uncompetitive NMDA Receptor Antagonists [MoA]; Sigma-1 Agonist [EPC]

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07-Jan-2021
30-Oct-2024
KGS
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DOSAGE - SUSPENSION, EXTENDED RELEASE;ORAL - ...DOSAGE - SUSPENSION, EXTENDED RELEASE;ORAL - EQ 30MG HYDROBROMIDE/5ML

USFDA APPLICATION NUMBER - 18658

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DOSAGE - TABLET, EXTENDED RELEASE;ORAL - 30MG...DOSAGE - TABLET, EXTENDED RELEASE;ORAL - 30MG;600MG

USFDA APPLICATION NUMBER - 21620

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DOSAGE - TABLET, EXTENDED RELEASE;ORAL - 60MG...DOSAGE - TABLET, EXTENDED RELEASE;ORAL - 60MG;1.2GM

USFDA APPLICATION NUMBER - 21620

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DOSAGE - SYRUP;ORAL - 2MG/5ML;10MG/5ML;30MG/5...DOSAGE - SYRUP;ORAL - 2MG/5ML;10MG/5ML;30MG/5ML

USFDA APPLICATION NUMBER - 88811

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