Alphamethylfentanyl
Encyclopedia
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". It was first identified in the bodies of two drug overdose victims in Orange County, California
, in December 1979, who appeared to have died from opiate overdose but tested negative for any known drugs of this type. Over the next year there were 13 more deaths and eventually the responsible agent was identified as α-methylfentanyl.
α-Methylfentanyl was significant as the first example of a "designer drug
" which had been developed entirely by clandestine chemists for sale as an illicit recreational drug rather than as a product of legitimate scientific research; while new synthetic drugs such as DOB
and ALD-52
had previously appeared on the black market, they had been reported in scientific research papers prior to their appearance as recreational drugs
.
α-Methylfentanyl was placed on the Schedule I list in September 1981, only two years after its appearance on the street, but already other analogues were being developed. Following the appearance of α-methylfentanyl on the market, over 10 new analogues of fentanyl have been reported, starting with para-fluorofentanyl
, followed by α-methylacetylfentanyl
, then by the highly potent 3-methylfentanyl
, and subsequently many others such as β-hydroxyfentanyl
, ohmefentanyl
, β-hydroxythiofentanyl
and β-hydroxy-4-methylfentanyl. The development of such a wide structural family of novel narcotic drugs was a major factor responsible for the implementation of the Federal Analog Act
which for the first time attempted to control entire families of drugs based on their structural similarity rather than scheduling each drug individually as they appeared. Whether this has been a successful strategy is debatable, it could be argued that specifying restrictions on new drugs which have never yet been made only encourages clandestine chemists to become more creative to attempt to circumvent the legal restrictions.
α-Methylfentanyl has similar effects to fentanyl. It is less potent by weight due to reduced binding affinity to its target
site, yet longer acting as the α-methyl group interferes with binding to metabolic enzymes which break the drug down. The independent discovery of the effect of the α-methyl group on fentanyl also marked the first time clandestine recreational-drug research had an effect on practical scientific research. Since fentanyl itself is highly potent and notorious for causing fatal overdoses when abused, and also very short lasting with addicts often administering doses every hour, α-methylfentanyl could have several advantages over the parent compound as a recreational drug. Side effects of fentanyl analogues are similar to those of fentanyl itself, which include itching, nausea
and potentially serious respiratory depression (namely with overdoses or improper drug-combinations, such as with benzodiazepines) which can be life-threatening. China White is anywhere from 10-1000 times more potent than heroin.
Fentanyl analogues such as α-methylfentanyl and 3-methylfentanyl
are often used as the "cut" in small amounts in normal Heroin stamps and bags, making them much more potent and profitable when sold as Heroin alone due to the advantage of raising the retail price per unit sold.
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.
α-Methylfentanyl was invented in 1976 and appeared on the black market under the name "China White". It was first identified in the bodies of two drug overdose victims in Orange County, California
Orange County, California
Orange County is a county in the U.S. state of California. Its county seat is Santa Ana. As of the 2010 census, its population was 3,010,232, up from 2,846,293 at the 2000 census, making it the third most populous county in California, behind Los Angeles County and San Diego County...
, in December 1979, who appeared to have died from opiate overdose but tested negative for any known drugs of this type. Over the next year there were 13 more deaths and eventually the responsible agent was identified as α-methylfentanyl.
α-Methylfentanyl was significant as the first example of a "designer drug
Designer drug
Designer drug is a term used to describe drugs that are created to get around existing drug laws, usually by preparing analogs or derivatives of existing drugs by modifying their chemical structure to varying degrees, or less commonly by finding drugs with entirely different chemical structures...
" which had been developed entirely by clandestine chemists for sale as an illicit recreational drug rather than as a product of legitimate scientific research; while new synthetic drugs such as DOB
2,5-Dimethoxy-4-bromoamphetamine
DOB, also known as Brolamfetamine and Bromo-DMA, is a psychedelic hallucinogenic drug and a substituted amphetamine of the phenethylamine class of compounds, which can be used as an entheogen. DOB was first synthesized by Alexander Shulgin in 1967...
and ALD-52
ALD-52
ALD-52, also known as N-acetyl-LSD, is a chemical analogue of lysergic acid diethylamide . It was originally discovered by Albert Hofmann but was not widely studied until the rise in popularity of psychedelics in the 1960s.- Effects :...
had previously appeared on the black market, they had been reported in scientific research papers prior to their appearance as recreational drugs
Recreational drug use
Recreational drug use is the use of a drug, usually psychoactive, with the intention of creating or enhancing recreational experience. Such use is controversial, however, often being considered to be also drug abuse, and it is often illegal...
.
α-Methylfentanyl was placed on the Schedule I list in September 1981, only two years after its appearance on the street, but already other analogues were being developed. Following the appearance of α-methylfentanyl on the market, over 10 new analogues of fentanyl have been reported, starting with para-fluorofentanyl
Parafluorofentanyl
Para-fluorofentanyl is an opioid analgesic that is an analogue of fentanyl.Para-fluorofentanyl was sold briefly on the black market in the early 1980s, before the introduction of the Federal Analog Act which for the first time attempted to control entire families of drugs based on their structural...
, followed by α-methylacetylfentanyl
Alphamethylacetylfentanyl
α-methylacetylfentanyl is an opioid analgesic that is an analogue of fentanyl.α-methylacetylfentanyl was sold briefly on the black market in the early 1980s, before the introduction of the Federal Analog Act which for the first time attempted to control entire families of drugs based on their...
, then by the highly potent 3-methylfentanyl
3-Methylfentanyl
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 .3-Methylfentanyl was first...
, and subsequently many others such as β-hydroxyfentanyl
Betahydroxyfentanyl
β-hydroxyfentanyl is an opioid analgesic that is an analogue of fentanyl.β-hydroxyfentanyl was sold briefly on the black market in the early 1980s, before the introduction of the Federal Analog Act which for the first time attempted to control entire families of drugs based on their structural...
, ohmefentanyl
Ohmefentanyl
Ohmefentanyl was discovered in 1995 and is an extremely potent analgesic drug which selectively binds to the µ-opioid receptor....
, β-hydroxythiofentanyl
Betahydroxythiofentanyl
β-hydroxythiofentanyl is an opioid analgesic that is an analogue of fentanyl.β-hydroxythiofentanyl was sold briefly on the black market in the early 1980s, before the introduction of the Federal Analog Act which for the first time attempted to control entire families of drugs based on their...
and β-hydroxy-4-methylfentanyl. The development of such a wide structural family of novel narcotic drugs was a major factor responsible for the implementation of the Federal Analog Act
Federal Analog Act
The Federal Analog Act, , is a controversial section of the United States Controlled Substances Act which allowed any chemical "substantially similar" to a controlled substance listed in Schedule I or II to be treated as if it were also listed in those schedules, but only if intended for human...
which for the first time attempted to control entire families of drugs based on their structural similarity rather than scheduling each drug individually as they appeared. Whether this has been a successful strategy is debatable, it could be argued that specifying restrictions on new drugs which have never yet been made only encourages clandestine chemists to become more creative to attempt to circumvent the legal restrictions.
α-Methylfentanyl has similar effects to fentanyl. It is less potent by weight due to reduced 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, yet longer acting as the α-methyl group interferes with binding to metabolic enzymes which break the drug down. The independent discovery of the effect of the α-methyl group on fentanyl also marked the first time clandestine recreational-drug research had an effect on practical scientific research. Since fentanyl itself is highly potent and notorious for causing fatal overdoses when abused, and also very short lasting with addicts often administering doses every hour, α-methylfentanyl could have several advantages over the parent compound as a recreational 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 (namely with overdoses or improper drug-combinations, such as with benzodiazepines) which can be life-threatening. China White is anywhere from 10-1000 times more potent than heroin.
Fentanyl analogues such as α-methylfentanyl and 3-methylfentanyl
3-Methylfentanyl
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 .3-Methylfentanyl was first...
are often used as the "cut" in small amounts in normal Heroin stamps and bags, making them much more potent and profitable when sold as Heroin alone due to the advantage of raising the retail price per unit sold.