3-Methylfentanyl
Clinical data | |
---|---|
Other names | 3-methylfentanyl, Mefentanyl |
Legal status | |
Legal status |
|
Identifiers | |
| |
JSmol) | |
Chirality | Racemic mixture |
| |
| |
(what is this?) (verify) |
3-Methylfentanyl (3-MF, mefentanyl) is an
Overview and history
3-methylfentanyl was first discovered in 1974
While 3-methylfentanyl was initially sold on the black market for only a short time between 1984 and 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]
The only country in the world with significant (200+ deaths a year, more than 10,000 addicts) abuse of this chemical is Estonia, where a dose of 3-MF costs 10 €, and other opiates are not generally available since the end of the 2000s.[7][8] Approximately 1100 deaths from fentanyl and 3-MF abuse were recorded in Estonia between 2005–2013, compared to approximately 450 deaths in Sweden, Germany, UK, Finland and Greece combined during the same period.[9]
Other opioid analogs even more potent still than 3-MF are known, such as carfentanil and ohmefentanyl,[10] but these are significantly more difficult to manufacture than 3-methylfentanyl. Since 2016 fentanyl seizures in Estonia contains mostly carfentanil or cyclopropylfentanyl.[11]
3-methylfentanyl has similar effects to fentanyl, but is far more potent due to increased binding affinity to its
Use as chemical weapon
3-Methylfentanyl was also reported by media as the identity of the anaesthetic "gas" Kolokol-1 delivered as an aerosol[12] during the Moscow theater hostage crisis in 2002 in which many hostages died from accidental overdoses, 3-methylfentanyl was later ruled out as the primary agent used. The opiate antidote naloxone was on-hand to treat the victims of the crisis, but, whether due to their incarceration, lack of food, or water, or sleep, or due to the novel nature of the still-unconfirmed compound used, acute symptoms continued to develop, resulting in many fatalities despite the administration of naloxone.[citation needed]
Synthesis
A number of methods for synthesis have been published. The most recent is probably the method posted by the Serbian chemical society (2004).[13]
There is another method, though, for constructing the N-Benzyl-3-methyl-4-piperidone in a 2-stage
See also
- 3-Methylbutyrfentanyl
- 4-Fluorofentanyl
- α-Methylfentanyl
- Acetylfentanyl
- Butyrfentanyl
- List of fentanyl analogues
References
- ^ Henderson GL. Designer Drugs: Past History and Future Prospects Journal of Forensic Sciences. 33(2): 569-575 (1988)
- PMID 6264594.
- PMID 8030414.
- PMID 4420811.
- PMID 7277090.
- PMID 1867667.
- S2CID 9626277.
- ^ "Drug market in Estonia". EMCDDA.
- ^ PMID 25976511.
- PMID 6239505.
- PMID 32416523.
- ^ "Moscow Theater Crisis: Unknown Chemical Agent Revisited". Bruker Detection. March 10, 2014.
- .