Structure via PubChem · Public domain (PubChem)
oripavine
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- Formula
- C18H19NO3
- Molecular weight
- 297.3 g/mol
- IUPAC name
- (4R,7aR,12bS)-7-methoxy-3-methyl-2,4,7a,13-tetrahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-9-ol
- SMILES
- CN1CC[C@]23[C@@H]4C(=CC=C2[C@H]1CC5=C3C(=C(C=C5)O)O4)OC
- InChIKey
- ZKLXUUYLEHCAMF-UUWFMWQGSA-N
- XLogP
- 1.9
- Polar surface area
- 41.9 Ų
- H-bond donors
- 1
- H-bond acceptors
- 4
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Wikidata facts
- Has part
- carbon
- Mass
- 297.136493
Show 5 more facts
- found in taxon
- Papaver orientale
- chemical formula
- C₁₈H₁₉NO₃
- isomeric SMILES
- CN1CC[C@]23[C@@H]4C(=CC=C2[C@H]1CC5=C3C(=C(C=C5)O)O4)OC
- canonical SMILES
- CN1CCC23C4C(=CC=C2C1CC5=C3C(=C(C=C5)O)O4)OC
- Commons category
- Oripavine
Sources (2)
via Wikidata · CC0
~5 min read
Encyclopedic overview
5 sectionsContents
- Pharmacological properties
- Bridged derivatives (The Bentley compounds)
- Legal status
- Biosynthesis
- References
Oripavine is an opioid and the major metabolite of thebaine. It is the precursor to the semi-synthetic compounds etorphine and buprenorphine. Although this chemical compound has analgesic potency comparable to morphine, it is not used clinically due to severe adverse effects and a low therapeutic index. Being a precursor to a series of extremely strong opioids, oripavine is a controlled substance in some jurisdictions.
== Pharmacological properties == Oripavine possesses an analgesic potency comparable to morphine; however, it is not clinically useful due to severe toxicity and low therapeutic index. In both mice and rats, toxic doses caused tonic-clonic seizures followed by death, similar to thebaine. Oripavine has a potential for dependence which is significantly greater than that of thebaine but slightly less than that of morphine.
Excerpted from Wikipedia’s “oripavine” article, available under the CC BY-SA 4.0 licence.