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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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01-Jul-2021
22-Oct-2024
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Quantity (KGS) & Unit rate (USD/KGS) over time

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ABOUT THIS PAGE

Oripavine Manufacturers

A Oripavine manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of Oripavine, including repackagers and relabelers. The FDA regulates Oripavine manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. Oripavine API Manufacturers are required to adhere to Good Manufacturing Practices (GMP) to ensure that their products are consistently manufactured to meet established quality criteria.

Oripavine Suppliers

A Oripavine supplier is an individual or a company that provides Oripavine active pharmaceutical ingredient (API) or Oripavine finished formulations upon request. The Oripavine suppliers may include Oripavine API manufacturers, exporters, distributors and traders.

Oripavine NDC

National Drug Code is a comprehensive database maintained by the FDA that contains information on all drugs marketed in the US. This directory includes information about finished drug products, unfinished drug products, and compounded drug products, including those containing Oripavine as an active pharmaceutical ingredient (API).

Finished drug products

The FDA updates the NDC directory daily. The NDC numbers for Oripavine API and other APIs are published in this directory by the FDA.

Unfinished drugs

The NDC unfinished drugs database includes product listing information submitted for all unfinished drugs, such as active pharmaceutical ingredients (APIs), drugs intended for further processing and bulk drug substances for compounding.

Pharmaceutical companies that manufacture Oripavine as an active pharmaceutical ingredient (API) must furnish the FDA with an updated record of all drugs that they produce, prepare, propagate, compound, or process for commercial distribution in the US at their facilities.

Compounded drug products

The NDC directory also contains data on finished compounded human drug products that contain Oripavine and are produced by outsourcing facilities. While these outsourcing facilities are not mandated to assign a Oripavine NDC to their finished compounded human drug products, they may choose to do so.

click here to find a list of Oripavine suppliers with NDC on PharmaCompass.

Oripavine GMP

Oripavine Active pharmaceutical ingredient (API) is produced in GMP-certified manufacturing facility.

GMP stands for Good Manufacturing Practices, which is a system used in the pharmaceutical industry to make sure that goods are regularly produced and monitored in accordance with quality standards. The FDA’s current Good Manufacturing Practices requirements are referred to as cGMP or current GMP which indicates that the company follows the most recent GMP specifications. The World Health Organization (WHO) has its own set of GMP guidelines, called the WHO GMP. Different countries can also set their own guidelines for GMP like China (Chinese GMP) or the EU (EU GMP).

PharmaCompass offers a list of Oripavine GMP manufacturers, exporters & distributors, which can be sorted by USDMF, JDMF, KDMF, CEP (COS), WC, API price, and more, enabling you to easily find the right Oripavine GMP manufacturer or Oripavine GMP API supplier for your needs.

Oripavine CoA

A Oripavine CoA (Certificate of Analysis) is a formal document that attests to Oripavine's compliance with Oripavine specifications and serves as a tool for batch-level quality control.

Oripavine CoA mostly includes findings from lab analyses of a specific batch. For each Oripavine CoA document that a company creates, the USFDA specifies specific requirements, such as supplier information, material identification, transportation data, evidence of conformity and signature data.

Oripavine may be tested according to a variety of international standards, such as European Pharmacopoeia (Oripavine EP), Oripavine JP (Japanese Pharmacopeia) and the US Pharmacopoeia (Oripavine USP).

Inform the supplier about your product requirements, specifying if you need a product with particular monograph like EP (Ph. Eur.), USP, JP, BP, or any other quality. In addition, clarify whether you need hydrochloride (HCl), anhydricum, base, micronisatum or a specific level of purity. To find reputable suppliers, utilize the filters and select those certified by GMP, FDA, or any other certification as per your requirement.
For your convenience, we have listed synonyms and CAS numbers to help you find the best supplier. The use of synonyms and CAS numbers can be helpful in identifying potential suppliers, but it is crucial to note that they might not always indicate the exact same product. It is important to confirm the product details with the supplier before making a purchase to ensure that it meets your requirements.
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