View source for Oripavine

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| ImageFile = Oripavine.png
| ImageSize = 
| IUPACName = 6,7,8,14-Tetradehydro-4,5α-epoxy-<BR>6-methoxy-17-methyl-morphinan-3-ol
| OtherNames = 3-O-demethyl-thebaine
| Section1 = {{Chembox Identifiers
| Abbreviations = 
| CASNo = 467-04-9
| EINECS = 207-385-6
| PubChem = 5462306
| SMILES = CN1CCC23C4C(=CC=C2 C1CC5=C3C(=C(C=C5)O)O4)OC
| InChI = 
| RTECS =
| MeSHName = Oripavine
| ChEBI =
| KEGG = C06175
| ATCCode_prefix = N02
| ATCCode_suffix = A
| ATC_Supplemental =}}
| Section2 = {{Chembox Properties
| Formula = 
| C=18 | H=19 | N=1 | O=3
| MolarMass = 297.348 g/mol
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| Section5 = {{Chembox Pharmacology
| AdminRoutes = [[subcutaneous|SC]]
| Bioavail = 
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| Legal_status =
| Legal_US = Schedule II
| Legal_UK =
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'''Oripavine''' is an [[opiate]] and the major metabolite of [[thebaine]]. It is the [[prototype|prototypical]] molecule of a [[ATC_code_N02#N02AE_Oripavine_derivatives|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 [[mouse|mice]] and [[rats]], toxic doses caused [[tonic-clonic_seizure]]s followed by death, similar to [[thebaine]].<ref name="yeh 1981">{{cite journal | last = Yeh | first = SY | title =  Analgesic activity and toxicity of oripavine and phi-dihydrothebaine in the mouse and rat | journal = Archives Internationales de Pharmacodynamie et de Therapie | year = 1981 | month = December | volume = 254 | issue = 2 | pages = p223&ndash;40 | id = PMID 6121539}}</ref>

Oripavine has a potential for [[Physical dependence|dependence]] which is significantly greater than that of [[thebaine]] but slightly less than that of [[morphine]].<ref name="drug bulletin">{{cite journal | first = Pierre | last = Chanoit | coauthors = et al. | publisher = [[WHO]] Advisory Group | url = http://www.unodc.org/unodc/en/bulletin/bulletin_1981-01-01_3_page004.html | title = Dependence potential of oripavine | journal = Bulletin on Narcotics | year = 1981 | volume = 33 | issue = 3 | pages = 29&ndash;35 | accessdate = 2007-10-05 | id = PMID 7039748}}</ref>

==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]].<ref>WHO Expert Committee on Drug Dependence. [http://whqlibdoc.who.int/trs/WHO_TRS_915.pdf "Thirty-third report"]. ''WHO Technical Report Series'', No. 915. Geneva, World Health Organization, 2003. Accessed [[September 17]] [[2007]]. </ref> On [[March 14]] [[2007]], the [[United Nations]] [[Commission on Narcotic Drugs]] formally decided to accept these recommendations, and placed oripavine in the Schedule I.<ref> 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." [http://www.unodc.org/unodc/en/cnd_session_50.html ''Report on the fiftieth session'']<!--Direct link to report PDF fails, this is the UNODC's linking page-->. Document E/CN.7/2007/16, p 52. Geneva, United Nations Office on Drugs and Crime, 2007. Accessed [[September 18]] [[2007]].</ref>

Until recently, oripavine was a [[Controlled_Substances_Act#Schedule_II_drugs|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.<ref>Drug Enforcement Administration. "[http://a257.g.akamaitech.net/7/257/2422/01jan20071800/edocket.access.gpo.gov/2007/E7-18524.htm Designation of Oripavine as a Basic Class of Controlled Substance.]" ''Federal Register''. September 2007; '''72''' (184):p54208-54210. Accessed [[October 25]] [[2007]].</ref>

==References==
<references/>

{{Opioids}}

[[Category:Natural opium alkaloids]]
[[Category:Opioids]]
[[Category:Drugs]]
{{WikiDoc Sources}}