This MedLibrary.org supplementary page on Oripavine is provided directly from the open source Wikipedia as a service to our readers. Please see the note below on authorship of this content, as well as the Wikipedia usage guidelines. To search for other content from our encyclopedia supplement, please use the form below:
Related Sponsors
| Oripavine | |
|---|---|
 |
|
| IUPAC name | 6,7,8,14-Tetradehydro-4,5α-epoxy- 6-methoxy-17-methyl-morphinan-3-ol |
| Other names | 3-O-demethyl-thebaine |
| Identifiers | |
| CAS number | [467-04-9] |
| PubChem | |
| EINECS number | |
| KEGG | |
| MeSH | |
| ATC code | N02 |
| SMILES |
|
| Properties | |
| Molecular formula | C18H19NO3 |
| Molar mass | 297.35 g mol-1 |
| Pharmacology | |
| Routes of administration |
SC |
| Legal status | |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox references |
|
Oripavine is an opiate and the major metabolite of thebaine. It is the prototypical molecule of a series of semi-synthetic opioids which includes buprenorphine. Although its analgesic potency is comparable to morphine, it is not used clinically due to its severe toxicity and low therapeutic index.
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.[1]
Oripavine has a potential for dependence which is significantly greater than that of thebaine but slightly less than that of morphine.[2]
Legal Status
Due to the relative ease of synthetic modification of oripavine to produce other narcotics (by either direct or indirect routes via thebaine), the World Health Organization's Expert Committee on Drug Dependence recommended in 2003 that oripavine be controlled under Schedule I of the 1961 Single Convention on Narcotic Drugs.[3] On March 14, 2007, the United Nations Commission on Narcotic Drugs formally decided to accept these recommendations, and placed oripavine in the Schedule I.[4]
Until recently, oripavine was a Schedule II drug in the United States by default as a thebaine derivative, although it was not explicitly listed. However, as a member state under the 1961 Single Convention on Narcotic Drugs, the US was obligated to specifically control the substance under the Controlled Substances Act following its international control by the UN Commission on Narcotic Drugs. On September 24, 2007, the Drug Enforcement Administration formally added oripavine to Schedule II.[5]
References
- ^ Yeh, SY (December 1981). "Analgesic activity and toxicity of oripavine and phi-dihydrothebaine in the mouse and rat". Archives Internationales de Pharmacodynamie et de Therapie 254 (2): p223–40. PMID 6121539.
- ^ Chanoit, Pierre; et al. (1981). "Dependence potential of oripavine". Bulletin on Narcotics 33 (3): 29–35. WHO Advisory Group. PMID 7039748. Retrieved on 2007-10-05.
- ^ WHO Expert Committee on Drug Dependence. "Thirty-third report". WHO Technical Report Series, No. 915. Geneva, World Health Organization, 2003. Accessed September 17, 2007.
- ^ UN Commission on Narcotic Drugs. "Decision 50/1: Inclusion of oripavine in Schedule I of the Single Convention on Narcotic Drugs of 1961 and that Convention as amended by the 1972 Protocol." Report on the fiftieth session. Document E/CN.7/2007/16, p 52. Geneva, United Nations Office on Drugs and Crime, 2007. Accessed September 18, 2007.
- ^ Drug Enforcement Administration. "Designation of Oripavine as a Basic Class of Controlled Substance." Federal Register. September 2007; 72 (184):p54208-54210. Accessed October 25, 2007.
Wikipedia content modification information:
- This page was last modified on 14 June 2008, at 00:42.
Wikipedia Authorship and Review
Wikipedia content provided here is not reviewed directly by MedLibrary.org. Wikipedia content is authored by an open community of volunteers and is not produced by or in any way affiliated with MedLibrary.org.
Wikipedia Usage Guidelines
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article on "Oripavine".
The URL for this specific entry is:
All Wikipedia text is available under the terms of the GNU Free Documentation License. (See Copyrights for details). Wikipedia® is a registered trademark of the Wikimedia Foundation, Inc.