3-Methylfentanyl
| 200px | |
| Systematic (IUPAC) name | |
|---|---|
|
(RS)-N-(3-methyl-1-phenethyl-4-piperidyl)-N-phenyl-propanamide | |
| Legal status | |
| Legal status |
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| Identifiers | |
| CAS Number | 42045-86-3 |
| PubChem | CID 61996 |
| ChemSpider | 55844 |
| Synonyms | 3-methylfentanyl, Mefentanyl |
| Chemical data | |
| Formula | C23H30N2O |
| Molar mass | 350.497 g/mol[[Script error: No such module "String".]] |
| Script error: No such module "collapsible list". | |
3-Methylfentanyl (3-MF, mefentanyl) is an opioid analgesic that is an analogue of fentanyl. 3-Methylfentanyl is one of the most potent drugs that has been widely sold on the black market, estimated to be between 400-6000 times stronger than morphine[1] depending on which isomer is used (with the cis isomer being the more potent one).[2][3]
3-Methylfentanyl was first discovered in 1974[4] and subsequently appeared on the street as an alternative to the clandestinely produced fentanyl analogue α-methylfentanyl. However, it quickly became apparent that 3-methylfentanyl was much more potent than α-methylfentanyl, and correspondingly even more dangerous.[5]
While 3-methylfentanyl was initially sold on the black market for only a short time between 1984–1985, its high potency made it an attractive target to clandestine drug producers, as racemic 3-MF is 10–15 times more potent than fentanyl and so correspondingly larger amounts of cut product for street sales can be produced for an equivalent amount of effort as for producing fentanyl itself; one gram of 3-methylfentanyl might be sufficient to produce several thousand dosage units once diluted for sale. 3-MF has thus reappeared several times, at various places around the world,[6] and is currently a problematic drug of abuse in Scandinavian and Eastern European countries such as Finland[7] and Estonia.[8]
Other opioid analogues even more potent still than 3-MF are known, such as carfentanil and ohmefentanyl,[9] but these are significantly more difficult to manufacture than 3-methylfentanyl and have not been so well accepted as street drugs.
3-Methylfentanyl has similar effects to fentanyl, but is far more potent due to increased binding affinity to its target site. Since fentanyl itself is already highly potent, 3-methylfentanyl is extremely dangerous when used recreationally, and has resulted in many deaths among opiate addicts using the drug. Side effects of fentanyl analogues are similar to those of fentanyl itself, which include itching, nausea and potentially serious respiratory depression which can be life-threatening.
Use as chemical weapon
3-Methylfentanyl was also reported by Russian media as the identity of the anaesthetic "gas" Kolokol-1 (actually an aerosol, of a free base dissolved in halothane) used in the Moscow theater hostage crisis in 2002, in which many hostages died from accidental overdoses of the narcotic. [10]
References
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<references />, or <references group="..." />- ↑ Henderson GL. Designer Drugs: Past History and Future Prospects Journal of Forensic Science. 33(2): 569-575 (1988)
- ↑ Jin, WQ; Xu; Zhu; Fang; Xia; Huang; Ge; Chi (1981). "Studies on synthesis and relationship between analgesic activity and receptor affinity for 3-methyl fentanyl derivatives". Scientia Sinica. 24 (5): 710–20. PMID 6264594. More than one of
|author2=and|last2=specified (help); More than one of|author3=and|last3=specified (help); More than one of|author4=and|last4=specified (help); More than one of|author5=and|last5=specified (help); More than one of|author6=and|last6=specified (help); More than one of|author7=and|last7=specified (help); More than one of|author8=and|last8=specified (help) - ↑ Wang, ZX; Zhu, YC; Chen, XJ; Ji, RY (1993). "Stereoisomers of 3-methylfentanyl: synthesis, absolute configuration and analgesic activity". Yao xue xue bao = Acta pharmaceutica Sinica. 28 (12): 905–10. PMID 8030414.
- ↑ Van Bever, W. F. M.; Niemegeers, C. J. E.; Janssen, P. A. J. (1974). "Synthetic analgesics. Synthesis and pharmacology of the diastereoisomers of N-[3-methyl-1-(2-phenylethyl)-4-piperidyl]-N-phenylpropanamide and N-[3-methyl-1-(1-methyl-2-phenylethyl)-4-piperidyl]-N-phenylpropanamide". Journal of Medicinal Chemistry. 17: 1047. doi:10.1021/jm00256a003.
- ↑ Ayres, WA; Starsiak; Sokolay (1981). "The bogus drug: Three methyl & alpha methyl fentanyl sold as "China White"". Journal of psychoactive drugs. 13 (1): 91–3. PMID 7277090. More than one of
|author2=and|last2=specified (help); More than one of|author3=and|last3=specified (help) - ↑ Hibbs, J; Perper; Winek (1991). "An outbreak of designer drug--related deaths in Pennsylvania". JAMA : the journal of the American Medical Association. 265 (8): 1011–3. doi:10.1001/jama.265.8.1011. PMID 1867667. More than one of
|author2=and|last2=specified (help); More than one of|author3=and|last3=specified (help) - ↑ Ojanperä, I.; Gergov, M.; Rasanen, I.; Lunetta, P.; Toivonen, S.; Tiainen, E.; Vuori, E. (2006). "Blood levels of 3-methylfentanyl in 3 fatal poisoning cases". The American journal of forensic medicine and pathology : official publication of the National Association of Medical Examiners. 27 (4): 328–331. doi:10.1097/01.paf.0000188097.78132.e5. PMID 17133031. More than one of
|author2=and|last2=specified (help); More than one of|author3=and|last3=specified (help); More than one of|author4=and|last4=specified (help); More than one of|author5=and|last5=specified (help); More than one of|author6=and|last6=specified (help); More than one of|author7=and|last7=specified (help) - ↑ Ojanperä, I.; Gergov, M.; Liiv, M.; Riikoja, A.; Vuori, E. (2008). "An epidemic of fatal 3-methylfentanyl poisoning in Estonia". International journal of legal medicine. 122 (5): 395–400. doi:10.1007/s00414-008-0230-x. PMID 18386033. More than one of
|author2=and|last2=specified (help); More than one of|author3=and|last3=specified (help); More than one of|author4=and|last4=specified (help); More than one of|author5=and|last5=specified (help) - ↑ Huang, ZM; Zhou; Chen; Zheng; Zhang; Chi; Li; Chen (1984). "Analgesic activity and toxicity of potent analgesics, ohmefentanyl and mefentanyl". Zhongguo yao li xue bao = Acta pharmacologica Sinica. 5 (3): 153–8. PMID 6239505. More than one of
|author2=and|last2=specified (help); More than one of|author3=and|last3=specified (help); More than one of|author4=and|last4=specified (help); More than one of|author5=and|last5=specified (help); More than one of|author6=and|last6=specified (help); More than one of|author7=and|last7=specified (help); More than one of|author8=and|last8=specified (help) - ↑ The Moscow News
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