Oripavin
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| Surname | Oripavin | |||||||||||||||
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| Molecular formula | C 18 H 19 NO 3 | |||||||||||||||
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| Molar mass | 297.35 g · mol -1 | |||||||||||||||
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| As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . | ||||||||||||||||
Oripavine is an alkaloid of the opiate group which is chemically related to thebaine , which it is also the main metabolite of.
Occurrence
Oripavin is the main component of the alkaloids in the milky sap of the oriental poppy seeds ( Papaver-orientale ), it contains up to 0.15%. (after Lyle E. Craker & James E. Simon)
pharmacology
Oripavin is a prototypical molecule for a number of semi-synthetic opiates such as B. Etorphine or Buprenorphine . Although its analgesic potency is close to that of morphine , it is not used medicinally due to its narrow therapeutic range and, above all, its high toxicity .
Tests with rats and mice showed that toxic doses trigger tonic-clonic seizures in the animals, followed by the death of the animal. A similar effect on test animals was also found in tests with thebaine.
Despite its toxic properties, oripavin has a relatively high potential for the development of addiction. This is significantly larger than that of thebaine, but slightly lower than that of morphine.
Legal situation
Due to the recognized abuse potential of oripavin, especially due to the simple synthetic process for converting it into potent opium derivatives for non-medical use, the WHO recommended that it be included in the narcotics control in 2003. In Germany, since March 2008, according to the BtMG amendment decision of February 18, 2008, Oripavin has been included in Annex II of the Narcotics Act (BtMG) as a marketable, but not prescribable substance.
In the USA , Oripavin is currently registered in Schedule II by the DEA (Drug Enforcement Administration) under the Controlled Substances Act . The substances listed in Schedule II are included according to three main points, an important one including the evaluation of the physical and psychological degree of dependence, as well as the therapeutic and medical benefit. Theoretically, Oripavin would therefore be prescribable, since Schedule II substances can be prescribed under strict regulatory supervision by the DEA. The system is comparable to BtMG Annex III in Germany, according to which these substances can be prescribed via officially controlled narcotic prescriptions.
literature
- Lyle E. Craker & James E. Simon - Herbs, Spices and Medicinal Plants (Volume 2)
Individual evidence
- ↑ a b Registration dossier on (5α) -6,7,8,14-tetradehydro-4,5-epoxy-6-methoxy-17-methylmorphinan-3-ol ( GHS section ) at the European Chemicals Agency (ECHA), accessed on July 10, 2020.
- ^ SY Yeh: Analgesic activity and toxicity of oripavine and phi-dihydrothebaine in the mouse and rat . In: Archives Internationales de Pharmacodynamie et de Therapy . 254, No. 2, December 1981, pp. 223-240. PMID 6121539 .
- ↑ Pierre Chanoit, et al .: Dependence potential of oripavine . In: WHO Advisory Group (Ed.): Bulletin on Narcotics . 33, No. 3, 1981, pp. 29-35. PMID 7039748 . Retrieved October 5, 2007.
- ^ WHO Expert Committee on Drug Dependence. Thirty-third report (PDF; 242 kB). WHO Technical Report Series , No. 915. Geneva, World Health Organization, 2003. Accessed September 17, 2007.
- ↑ Title 21 United States Code (USC) Controlled Substances Act. In: usdoj.gov. DEA , accessed April 16, 2017 .