The Full Wiki

More info on 3-Methylfentanyl

3-Methylfentanyl: Wikis

  
  

Note: Many of our articles have direct quotes from sources you can cite, within the Wikipedia article! This article doesn't yet, but we're working on it! See more info or our list of citable articles.

Encyclopedia

From Wikipedia, the free encyclopedia

1 : 1 mixture (racemate)
Systematic (IUPAC) name
(RS)-N-(3-methyl-1-phenethyl-4-piperidyl)- N-phenyl-propanamide
Identifiers
CAS number 42045-86-3
ATC code  ?
PubChem 61996
ChemSpider 55844
Chemical data
Formula C 23H30N2O 
Mol. mass 350.497 g/mol
SMILES eMolecules & PubChem
Synonyms 3-methylfentanyl, Mefentanyl
Pharmacokinetic data
Bioavailability  ?
Metabolism  ?
Half life  ?
Excretion  ?
Therapeutic considerations
Pregnancy cat.  ?
Legal status Schedule I (CA) Class A (UK) Schedule I (US)
Routes  ?

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

  1. ^ Henderson GL. Designer Drugs: Past History and Future Prospects Journal of Forensic Science. 33(2): 569-575 (1988)
  2. ^ 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.   edit
  3. ^ Wang, ZX; Zhu; Chen; Ji (1993). "Stereoisomers of 3-methylfentanyl: synthesis, absolute configuration and analgesic activity". Yao xue xue bao = Acta pharmaceutica Sinica 28 (12): 905–10. PMID 8030414.   edit
  4. ^ Van Bever, W. F. M.; Niemegeers; Janssen (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.   edit
  5. ^ 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.   edit
  6. ^ 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.   edit
  7. ^ 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.   edit
  8. ^ 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.   edit
  9. ^ 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.   edit
  10. ^ The Moscow News







Got something to say? Make a comment.
Your name
Your email address
Message