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2D Structure
Also known as: 5965-13-9, Df 118, Codeine, dihydro-, tartrate (1:1), 8lxs95bsa9, Tuscodin, Dihydrocodeine bitartrate [usp]
Molecular Formula
C22H29NO9
Molecular Weight
451.5  g/mol
InChI Key
ZGSZBVAEVPSPFM-HYTSPMEMSA-N
FDA UNII
8LXS95BSA9

Dihydrocodeine Bitartrate is a synthetic opioid analgesic. Dihydrocodeine bitartrate mimics the actions of the endogenous opioid peptides due to its agonistic effects on the opioid receptors. Stimulation of the mu receptors produces the typical narcotic effects of analgesia, miosis, euphoria, respiratory depression, sedation, physical dependence and bradycardia. Dihydrocodeine bitartrate is twice as potent as codeine and has one third of the potency of morphine. This analgesic is used for the relief of moderate to moderately severe pain.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(4R,4aR,7S,7aR,12bS)-9-methoxy-3-methyl-2,4,4a,5,6,7,7a,13-octahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-ol;(2R,3R)-2,3-dihydroxybutanedioic acid
2.1.2 InChI
InChI=1S/C18H23NO3.C4H6O6/c1-19-8-7-18-11-4-5-13(20)17(18)22-16-14(21-2)6-3-10(15(16)18)9-12(11)19;5-1(3(7)8)2(6)4(9)10/h3,6,11-13,17,20H,4-5,7-9H2,1-2H3;1-2,5-6H,(H,7,8)(H,9,10)/t11-,12+,13-,17-,18-;1-,2-/m01/s1
2.1.3 InChI Key
ZGSZBVAEVPSPFM-HYTSPMEMSA-N
2.1.4 Canonical SMILES
CN1CCC23C4C1CC5=C2C(=C(C=C5)OC)OC3C(CC4)O.C(C(C(=O)O)O)(C(=O)O)O
2.1.5 Isomeric SMILES
CN1CC[C@]23[C@@H]4[C@H]1CC5=C2C(=C(C=C5)OC)O[C@H]3[C@H](CC4)O.[C@@H]([C@H](C(=O)O)O)(C(=O)O)O
2.2 Other Identifiers
2.2.1 UNII
8LXS95BSA9
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Contugesic

2. Df 118

3. Dhc Continus

4. Dhc Mundipharma

5. Dicodin

6. Dihydrocodeine

7. Dihydrocodeine Acetate, (5alpha,6alpha)-isomer

8. Dihydrocodeine Hydrochloride, (5alpha,6alpha)-isomer

9. Dihydrocodeine Phosphate (1:1), (5alpha,6alpha)-isomer

10. Dihydrocodeine Tartrate (1:1), (5alpha,6alpha)-(r-(r*,r*))-isomer

11. Dihydrocodeine Tartrate (1:1), (5alpha,6beta)-(r-(r*,r*))-isomer

12. Dihydrocodeine, (5alpha,6alpha,14alpha)-isomer

13. Dihydrocodeine, (5alpha,6beta)-isomer

14. Dihydrocodeine, (5alpha,6beta,14alpha)-isomer

15. Dihydrocodeine, Thiocyanate Salt (5alpha,6alpha)-isomer

16. Paracodin

17. Paracodina

18. Paramol 118

19. Rikodeine

20. Tiamon

21. Tosidrin

2.3.2 Depositor-Supplied Synonyms

1. 5965-13-9

2. Df 118

3. Codeine, Dihydro-, Tartrate (1:1)

4. 8lxs95bsa9

5. Tuscodin

6. Dihydrocodeine Bitartrate [usp]

7. Paracodeine Bitartrate

8. Dihydrocodeine Tartrate

9. Dihydrocodeine Acid Tartrate

10. Dihydrocodeine Hydrogen Tartrate

11. Dihydrocodeine Bitartrate (usp)

12. Unii-8lxs95bsa9

13. Nsc-117857

14. (4r,4ar,7s,7ar,12bs)-9-methoxy-3-methyl-2,4,4a,5,6,7,7a,13-octahydro-1h-4,12-methanobenzofuro[3,2-e]isoquinoline-7-ol;(2r,3r)-2,3-dihydroxybutanedioic Acid

15. Einecs 227-747-7

16. Nsc 117857

17. Dtxsid00975047

18. Dihydrocodeine Tartrate [mi]

19. Dihydrocodeine Tartrate [mart.]

20. Dihydrocodeine Bitartrate [vandf]

21. Dihydrocodeine Bitartrate [usp-rs]

22. Dihydrocodeine Bitartrate [who-dd]

23. D03825

24. Dihydrocodeine Bitartrate [orange Book]

25. Dihydrocodeine Bitartrate [usp Monograph]

26. Trezix Component Dihydrocodeine Bitartrate

27. Dhc Plus Component Dihydrocodeine Bitartrate

28. Dihydrocodeine Bitartrate Component Of Dhc Plus

29. Dihydrocodeine Hydrogen Tartrate [ep Monograph]

30. Q27270730

31. Synalgos-dc Component Dihydrocodeine Bitartrate

32. Dihydrocodeine Bitartrate Component Of Synalgos-dc

33. Synalgos-dc-a Component Dihydrocodeine Bitartrate

34. Dihydrocodeine Bitartrate Component Of Synalgos-dc-a

35. 4,5.alpha.-epoxy-3-methoxy-17-methylmorphinan-6a-ol (+)-tartrate (salt)

36. 4,5alpha-epoxy-6alpha-hydroxy-3-methoxy-17-methylmorphinan Hydrogen (r-(r*,r*))-tartrate

37. Morphinan-6-alpha-ol, 4,5-alpha-epoxy-3-methoxy-17-methyl-, Tartrate (1:1)

38. Morphinan-6alpha-ol, 4,5alpha-epoxy-3-methoxy-17-methyl-, Tartrate (1:1) (salt)

39. (4r,4ar,7s,7ar,12bs)-9-methoxy-3-methyl-2,4,4a,5,6,7,7a,13-octahydro-1h-4,12-methanobenzofuro[3,2-e]isoquinolin-7-ol;(2r,3r)-2,3-dihydroxybutanedioic Acid

40. Morphinan-6-ol, 4,5-epoxy-3-methoxy-17-methyl-, (5.alpha.,6.alpha.)-2,3-dihydroxybutanedioate (1:1) (salt)

41. Morphinan-6-ol, 4,5-epoxy-3-methoxy-17-methyl-, (5alpha,6alpha)-, (r-(r*,r*))-2,3-dihydroxybutanedioate (1:1) (salt)

2.4 Create Date
2005-08-09
3 Chemical and Physical Properties
Molecular Weight 451.5 g/mol
Molecular Formula C22H29NO9
Hydrogen Bond Donor Count5
Hydrogen Bond Acceptor Count10
Rotatable Bond Count4
Exact Mass451.18423150 g/mol
Monoisotopic Mass451.18423150 g/mol
Topological Polar Surface Area157 Ų
Heavy Atom Count32
Formal Charge0
Complexity605
Isotope Atom Count0
Defined Atom Stereocenter Count7
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count2
4 Pharmacology and Biochemistry
4.1 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.)