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Oripavine



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 5462306
EINECS number 207-385-6
KEGG C06175
MeSH Oripavine
ATC code N02A
SMILES CN1CCC23C4C(=CC=C2 C1CC5=C3C(=C(C=C5)O)O4)OC
Properties
Molecular formula C18H19NO3
Molar mass 297.35 g mol-1
Pharmacology
Routes of
administration
SC
Legal status


Schedule II(US)

Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)
Infobox disclaimer and 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.

Additional recommended knowledge

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

  1. ^ 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.
  2. ^ 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.
  3. ^ WHO Expert Committee on Drug Dependence. "Thirty-third report". WHO Technical Report Series, No. 915. Geneva, World Health Organization, 2003. Accessed September 17 2007.
  4. ^ 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.
  5. ^ 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.
 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Oripavine". A list of authors is available in Wikipedia.
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