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Chemistry

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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
oripavine is a natural product found in Papaver bracteatum, Papaver orientale, and other organisms with data available.
1 2D Structure

Oripavine

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)


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05-May-2021
22-Oct-2024
KGS
overview
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Average Price (USD/KGS)

Number of Transactions

Total Quantity (KGS)

Total Value (USD)

Quantity (KGS) & Unit rate (USD/KGS) over time

API Imports and Exports

Importing Country Total Quantity
(KGS)
Average Price
(USD/KGS)
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