Oripavine

Oripavine
Names
IUPAC name
6,7,8,14-Tetradehydro-4,5α-epoxy-6-methoxy-17-methylmorphinan-3-ol
Other names
3-O-desmethylthebaine
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.006.715 Edit this at Wikidata
EC Number
  • 207-385-6
KEGG
MeSH Oripavine
UNII
  • 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 checkY
    Key: ZKLXUUYLEHCAMF-UUWFMWQGSA-N checkY
  • 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
    Key: ZKLXUUYLEHCAMF-UUWFMWQGBL
  • Key: ZKLXUUYLEHCAMF-UUWFMWQGSA-N
  • OC1=C(O[C@H]2C(OC)=CC=C3[C@@]42CCN5C)C4=C(C[C@H]35)C=C1
Properties
C18H19NO3
Molar mass 297.348 g/mol
Pharmacology
N02A (WHO)
SC
Legal status
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Oripavine is an opioid and the major metabolite of thebaine. It is the parent compound from which a series of semi-synthetic opioids are derived, which includes the compounds etorphine and buprenorphine. Although its analgesic potency is comparable to morphine, it is not used clinically due to its severe toxicity and low therapeutic index. Being a precursor to a series of extremely strong opioids, oripavine is a controlled substance in some jurisdictions.