Oripavine
 |
|
| Names | |
|---|---|
|
IUPAC name
6,7,8,14-Tetradehydro-4,5α-epoxy-6-methoxy-17-methylmorphinan-3-ol
|
|
| Other names
3-O-demethyl-thebaine
|
|
| Identifiers | |
|
3D model (Jmol)
|
|
| ChemSpider | |
| ECHA InfoCard | 100.006.715 |
| EC Number | 207-385-6 |
| KEGG | |
| MeSH | Oripavine |
|
PubChem CID
|
|
| UNII | |
|
|
|
|
| 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).
|
|
 (what is   ?) |
|
| Infobox references | |
Oripavine is an opiate 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. Due to its use in manufacture of strong opioids, oripavine is controlled substance in some jurisdictions.
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.
Of much greater relevance are the properties of the orvinols, a large family of semi-synthetic oripavine derivatives classically synthesized by the Diels-Alder reaction of thebaine with an appropriate dienophile followed by 3-O-demethylation to the corresponding bridged oripavine. These compounds were developed by the group led by K. W. Bentley in the 1960s, and these Bentley compounds represent the first series of "super-potent" μ-opioid agonists, with some compounds in the series being over 10,000 times the potency of morphine as an analgesic. The simple bridged oripavine parent compound 6,14-Endoethenotetrahydrooripavine is already 40 times the potency of morphine, but adding a branched tertiary alcohol substituent on the C7 position results in a wide range of highly potent compounds.
...
Wikipedia