3-Methylfentanyl

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3-Methylfentanyl
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Clinical data
Synonyms3-methylfentanyl, Mefentanyl
Legal status
Legal status
Identifiers
CAS Number
PubChem CID
E number{{#property:P628}}
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Chemical and physical data
FormulaC23H30N2O
Molar mass350.497 g/mol

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 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 corespondingly 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 10-15x 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.

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

  1. Henderson GL. Designer Drugs: Past History and Future Prospects Journal of Forensic Science. 33(2): 569-575 (1988)
  2. Jin WQ, Xu H, Zhu YC, Fang SN, Xia XL, Huang ZM, Ge BL, Chi ZQ. Studies on synthesis and relationship between analgesic activity and receptor affinity for 3-methyl fentanyl derivatives. Scientia Sinica. 1981 May;24(5):710-20.
  3. Wang ZX, Zhu YC, Chen XJ, Ji RY. Stereoisomers of 3-methylfentanyl: synthesis, absolute configuration and analgesic activity. Yao Xue Xue Bao. 1993;28(12):905-10. (Chinese)
  4. Willem F. M. Van Bever, Carlos J. E. Niemegeers, and Paul A. J. Janssen. 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 1974; 17(10): 1047-1051
  5. Ayres WA, Starsiak MJ, Sokolay P. The bogus drug: Three methyl & alpha methyl fentanyl sold as "China White". Journal of Psychoactive Drugs. 1981 Jan-Mar;13(1):91-3.
  6. Hibbs J, Perper J, Winek CL. An outbreak of designer drug--related deaths in Pennsylvania. Journal of the American Medical Association. 1991 Feb 27;265(8):1011-3.
  7. Ojanpera I, Gergov M, Rasanen I, Lunetta P, Toivonen S, Tiainen E, Vuori E. Blood levels of 3-methylfentanyl in 3 fatal poisoning cases. American Journal of Forensic Medicine and Pathology. 2006 Dec;27(4):328-31.
  8. UN Office on Drugs and Crime. 2006 World Drug Report.
  9. Huang ZM, Zhou J, Chen XJ, Zheng WJ, Zhang HP, Chi ZQ, Li ZG, Chen WL. Analgesic activity and toxicity of potent analgesics, ohmefentanyl and mefentanyl. Zhongguo Yao Li Xue Bao. 1984 Sep;5(3):153-8. (Chinese)
  10. http://english.mn.ru/english/issue.php?2004-41-2

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