3-Methylfentanyl
Encyclopedia
3-Methylfentanyl 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
depending on which isomer
is used (with the cis isomer being the more potent one).
3-Methylfentanyl was first discovered in 1974 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.
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, and is currently a problematic drug of abuse in Scandinavian and Eastern European countries such as Finland
and Estonia
.
Other opioid analogues even more potent still than 3-MF are known, such as carfentanil
and ohmefentanyl
, 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.
(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.
Opioid
An opioid is a psychoactive chemical that works by binding to opioid receptors, which are found principally in the central and peripheral nervous system and the gastrointestinal tract...
analgesic
Analgesic
An analgesic is any member of the group of drugs used to relieve pain . The word analgesic derives from Greek an- and algos ....
that is an analogue
Analog (chemistry)
In chemistry, a structural analog , also known as chemical analog or simply analog, is a compound having a structure similar to that of another one, but differing from it in respect of a certain component. It can differ in one or more atoms, functional groups, or substructures, which are replaced...
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
Morphine
Morphine is a potent opiate analgesic medication and is considered to be the prototypical opioid. It was first isolated in 1804 by Friedrich Sertürner, first distributed by same in 1817, and first commercially sold by Merck in 1827, which at the time was a single small chemists' shop. It was more...
depending on which isomer
Isomer
In chemistry, isomers are compounds with the same molecular formula but different structural formulas. Isomers do not necessarily share similar properties, unless they also have the same functional groups. There are many different classes of isomers, like stereoisomers, enantiomers, geometrical...
is used (with the cis isomer being the more potent one).
3-Methylfentanyl was first discovered in 1974 and subsequently appeared on the street as an alternative to the clandestinely produced fentanyl analogue α-methylfentanyl
Alphamethylfentanyl
α-Methylfentanyl is an opioid analgesic that is an analogue of fentanyl.α-Methylfentanyl was invented in 1976 and appeared on the black market under the name "China White"...
. However, it quickly became apparent that 3-methylfentanyl was much more potent than α-methylfentanyl, and correspondingly even more dangerous.
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, and is currently a problematic drug of abuse in Scandinavian and Eastern European countries such as Finland
Finland
Finland , officially the Republic of Finland, is a Nordic country situated in the Fennoscandian region of Northern Europe. It is bordered by Sweden in the west, Norway in the north and Russia in the east, while Estonia lies to its south across the Gulf of Finland.Around 5.4 million people reside...
and Estonia
Estonia
Estonia , officially the Republic of Estonia , is a state in the Baltic region of Northern Europe. It is bordered to the north by the Gulf of Finland, to the west by the Baltic Sea, to the south by Latvia , and to the east by Lake Peipsi and the Russian Federation . Across the Baltic Sea lies...
.
Other opioid analogues even more potent still than 3-MF are known, such as carfentanil
Carfentanil
Carfentanil or carfentanyl is an analogue of the popular synthetic opioid analgesic fentanyl, and is one of the most potent opioids known . Carfentanil was first synthesized in 1974 by a team of chemists at Janssen Pharmaceutica which included Paul Janssen...
and ohmefentanyl
Ohmefentanyl
Ohmefentanyl was discovered in 1995 and is an extremely potent analgesic drug which selectively binds to the µ-opioid receptor....
, 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
Mu Opioid receptor
The μ-opioid receptors are a class of opioid receptors with high affinity for enkephalins and beta-endorphin but low affinity for dynorphins. They are also referred to as μ opioid peptide receptors. The prototypical μ receptor agonist is the opium alkaloid morphine; μ refers to morphine...
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
Nausea
Nausea , is a sensation of unease and discomfort in the upper stomach with an involuntary urge to vomit. It often, but not always, precedes vomiting...
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-1Kolokol-1
Kolokol-1 is a synthetic opioid, developed for use as an aerosolizable incapacitating agent. Although the exact chemical structure has not yet been revealed, it is thought to be a derivative of the potent opioid fentanyl, most probably 3-methylfentanyl dissolved in halothane as an organic...
(actually an aerosol, of a free base dissolved in halothane
Halothane
Halothane is an inhalational general anesthetic. Its IUPAC name is 2-bromo-2-chloro-1,1,1-trifluoroethane. It is the only inhalational anesthetic agent containing a bromine atom; there are several other halogenated anesthesia agents which lack the bromine atom and do contain the fluorine and...
) used in the Moscow theater hostage crisis
Moscow theater hostage crisis
The Moscow theater hostage crisis, also known as the 2002 Nord-Ost siege, was the seizure of the crowded Dubrovka Theater on 23 October 2002 by some 40 to 50 armed Chechens who claimed allegiance to the Islamist militant separatist movement in Chechnya. They took 850 hostages and demanded the...
in 2002, in which many hostages died from accidental overdoses of the narcotic.