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    Chemistry

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    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 Tartrate
    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

    Dihydrocodeine Tartrate

    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.)

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    09-Aug-2024
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