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    Oripavine

    ACTIVE PHARMA INGREDIENTS

    MARKET PLACE

    PharmaCompass
    $ API Ref.Price (USD/KG) : 449Xls

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    2D Structure
    Also known as: 467-04-9, 575aou51cr, Chebi:7782, Einecs 207-385-6, Brn 0046094, Unii-575aou51cr
    Molecular Formula
    C18H19NO3
    Molecular Weight
    297.3  g/mol
    InChI Key
    ZKLXUUYLEHCAMF-UUWFMWQGSA-N
    FDA UNII
    575AOU51CR
    oripavine is a natural product found in Papaver bracteatum, Papaver orientale, and other organisms with data available.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (4R,7aR,12bS)-7-methoxy-3-methyl-2,4,7a,13-tetrahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-9-ol
    2.1.2 InChI
    InChI=1S/C18H19NO3/c1-19-8-7-18-11-4-6-14(21-2)17(18)22-16-13(20)5-3-10(15(16)18)9-12(11)19/h3-6,12,17,20H,7-9H2,1-2H3/t12-,17+,18+/m1/s1
    2.1.3 InChI Key
    ZKLXUUYLEHCAMF-UUWFMWQGSA-N
    2.1.4 Canonical SMILES
    CN1CCC23C4C(=CC=C2C1CC5=C3C(=C(C=C5)O)O4)OC
    2.1.5 Isomeric SMILES
    CN1CC[C@]23[C@@H]4C(=CC=C2[C@H]1CC5=C3C(=C(C=C5)O)O4)OC
    2.2 Other Identifiers
    2.2.1 UNII
    575AOU51CR
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 6-demethoxythebaine

    2. O(3)-dimethylthebaine

    3. Oripavine Hydrochloride, (5alpha)-isomer

    2.3.2 Depositor-Supplied Synonyms

    1. 467-04-9

    2. 575aou51cr

    3. Chebi:7782

    4. Einecs 207-385-6

    5. Brn 0046094

    6. Unii-575aou51cr

    7. 6,7,8,14-tetradehydro-4,5alpha-epoxy-6-methoxy-17-methylmorphinan-3-ol (oripavine)

    8. 3-o-demethylthebaine

    9. Oripavine [mi]

    10. (5alpha)-6,7,8,14-tetradehydro-4,5-epoxy-6-methoxy-17-methylmorphinan-3-ol

    11. 6,7,8,14-tetradehydro-4,5-alpha-epoxy-6-methoxy-17-methyl-morphinan-3-ol

    12. Schembl37889

    13. 4-27-00-02270 (beilstein Handbook Reference)

    14. Chembl437602

    15. Ids-no-010

    16. Dea No. 9330

    17. Schembl19880919

    18. Hsdb 8324

    19. Dtxsid10196908

    20. Morphinan-3-ol, 6,7,8,14-tetradehydro-4,5-epoxy-6-methoxy-17-methyl-, (5.alpha.)-

    21. Oripavine 0.1 Mg/ml In Methanol

    22. (4r,7ar,12bs)-7-methoxy-3-methyl-2,4,7a,13-tetrahydro-1h-4,12-methanobenzofuro[3,2-e]isoquinoline-9-ol

    23. Morphinan-3-ol, 6,7,8,14-tetradehydro-4,5-alpha-epoxy-6-methoxy-17-methyl-

    24. C06175

    25. Morphine Sulfate Impurity C [ep Impurity]

    26. Q420639

    27. Codeine Monohydrate Impurity L [ep Impurity]

    28. Codeine Hydrochloride Dihydrate Impurity L [ep Impurity]

    29. Codeine Phosphate Hemihydrate Impurity L [ep Impurity]

    30. 6,7,8,14-tetradehydro-4,5.alpha.-epoxy-6-methoxy-17-methylmorphinan-3-ol

    31. (1s,5r,13r)-14-methoxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0?,??.0?,??.0?,??]octadeca-7,9,11(18),14,16-pentaen-10-ol

    2.4 Create Date
    2005-06-24
    3 Chemical and Physical Properties
    Molecular Weight 297.3 g/mol
    Molecular Formula C18H19NO3
    XLogP31.9
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count4
    Rotatable Bond Count1
    Exact Mass297.13649347 g/mol
    Monoisotopic Mass297.13649347 g/mol
    Topological Polar Surface Area41.9 Ų
    Heavy Atom Count22
    Formal Charge0
    Complexity571
    Isotope Atom Count0
    Defined Atom Stereocenter Count3
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Pharmacology and Biochemistry
    4.1 Metabolism/Metabolites

    1. Codeine O-demethylation to morphine is mediated by cytochrome P450 IID1 (rat), or P450 IID6 (man), and exhibits genetic polymorphism. Thebaine is a precursor in the formation of endogenous morphine and codeine in man, being O-demethylated to oripavine. 2. The objective of the present study was to ascertain whether the O-demethylation of thebaine to oripavine was mediated by cytochrome P450 IID1 in rat liver microsomes. 3. Thebaine O-demethylation showed strain differences in female Sprague-Dawley (SD) and female Dark-Agouti (DA) rats, which serve as a model for the human debrisoquine/sparteine metabolism phenotypes. 4. The total intrinsic clearance of thebaine to oripavine was high (19.7 ml/h per mg protein) in SD rats, indicating that oripavine is a major metabolite of thebaine. A 3-fold lower intrinsic clearance was observed in DA rats (6.7 ml/h per mg protein). 5. Thebaine O-demethylation was inhibited by quinine and known substrates of cytochrome P450 IID1/P450 IID6, supporting the major involvement of cytochrome P450 IID1 in oripavine formation in rats.

    PMID:1763524 Mikus G et al; Xenobiotica 21 (11): 1501-9 (1991)

    Thebaine, an intermediate of morphine biosynthesis in the poppy plant, Papaver somniferum, was transformed to oripavine, codeine, and morphine by rat liver, kidney, and brain microsomes in the presence of an NADPH-generating system. The formation of morphine, codeine, and oripavine was identified by a specific RIA, HPLC, and GCMS. Thebaine also gave rise to four other compounds, which for the moment are unidentified. NADH dramatically increased the formation of both codeine and morphine when used together with an NADPH-generating system, especially in liver microsomes. NADPH is essential in the formation of oripavine from thebaine and morphine from codeine, while NADH is critical in the conversion of thebaine to codeine and from oripavine to morphine. Carbon monoxide or SKF 525A inhibited the conversion, indicating a role of cytochrome P-450. These results provide evidence for the enzymatic in vitro conversion by mammalian tissues of thebaine to morphine. The pathway is similar to that which exists in plants.

    PMID:3422490 Full text: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC279748 Kodaira H, Spector S; Proc Natl Acad Sci U S A 85 (4): 1267-71 (1988)