α-Methylfentanyl was discovered by a team at Janssen Pharmaceutica in the 1960s.[1] In 1976, it began to appear mixed with heroin, as an additive, and the mixture was sometimes also called "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.[2] Over the next year, there were 13 more deaths, and eventually the responsible agent was identified as α-methylfentanyl.[3]
A bag of "China White" α-methylfentanyl.
α-Methylfentanyl was placed on the U.S. Schedule I list in September 1981, only two years after its appearance on the street, but already other analogs were being developed. Following the appearance of α-methylfentanyl on the market, over ten new analogs of fentanyl have been reported, starting with para-fluorofentanyl, followed by α-methylacetylfentanyl, then by the highly potent 3-methylfentanyl, and subsequently by many others such as β-hydroxyfentanyl, ohmefentanyl, β-hydroxythiofentanyl and β-hydroxy-4-methylfentanyl.[4] 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 new drug analogs individually as each appeared.
The chemical structure of fentanyl has been used as a basis in modern chemistry for the discovery and nomenclature of many new fentanyl analogues, sometimes called fentalogs.
In 1991, a group of Russian chemistry students discovered a simplified synthesis route which used phosgene instead of phenethylamine.[5] Soon, abuse of the drug became widespread, causing a tenth of overdoses in the Moscow region. α-Methylfentanyl became notorious for low safety, and production declined.[citation needed]
Effects
This section needs more reliable medical references for verification or relies too heavily on primary sources. Please review the contents of the section and add the appropriate references if you can. Unsourced or poorly sourced material may be challenged and removed. Find sources: "Α-Methylfentanyl" – news · newspapers · books · scholar · JSTOR(November 2013)
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.[6]
Since fentanyl itself is highly potent and notorious for causing fatal overdoses when abused, and also very short lasting with recreational users often administering doses every hour, α-methylfentanyl could have several advantages over the parent compound as a recreational drug. Side effects of fentanyl analogs 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.
Fentanyl analogs such as α-methylfentanyl and 3-methylfentanyl are often used as the "cut" in small amounts in normal heroin stamps and bags, making them more potent and profitable than when sold as heroin alone due to the advantage of raising the retail price and potency per unit sold.
^Kram TC, Cooper DA, Allen AC (1981). "Behind the identification of China White". Analytical Chemistry. 53 (12): 1379A–1386A. doi:10.1021/ac00235a003. PMID 7294353.
^Gillespie TJ, Gandolfi AJ, Davis TP, Morano RA (1982). "Identification and quantification of alpha-methylfentanyl in post mortem specimens". Journal of Analytical Toxicology. 6 (3): 139–142. doi:10.1093/jat/6.3.139. PMID 7109557.
^Henderson GL. Designer Drugs: Past History and Future Prospects (1988). "Designer drugs: Past history and future prospects". Journal of Forensic Sciences. 33 (2): 569–575. doi:10.1520/JFS11976J. PMID 3286815.
^CHAZAN, GUY (May 27, 1993). "The trade in illegal narcotics looks set to mushroom..." United Press International. Retrieved April 6, 2017.
methylfentanyl, alpha, methylfentanyl, opioid, analgesic, that, analog, fentanyl, sometimes, sold, china, white, clinical, datatrade, nameschina, whiteatc, codenonelegal, statuslegal, statusau, prohibited, substance, schedule, anlage, authorized, scientific, o. a Methylfentanyl or alpha Methylfentanyl an opioid analgesic that is an analog of fentanyl It is sometimes sold as China White a MethylfentanylClinical dataTrade namesChina WhiteATC codenoneLegal statusLegal statusAU S9 Prohibited substance CA Schedule I DE Anlage I Authorized scientific use only UK Class A US Schedule IIdentifiersIUPAC name N phenyl N 1 1 phenylpropan 2 yl piperidin 4 yl propanamideCAS Number79704 88 4 YPubChem CID62281DrugBankDB01557 YChemSpider56081 YUNII8FU589W85CCompTox Dashboard EPA DTXSID60273955Chemical and physical dataFormulaC 23H 30N 2OMolar mass350 506 g mol 13D model JSmol Interactive imageSMILES O C N c1ccccc1 C3CCN C Cc2ccccc2 C CC3 CCInChI InChI 1S C23H30N2O c1 3 23 26 25 21 12 8 5 9 13 21 22 14 16 24 17 15 22 19 2 18 20 10 6 4 7 11 20 h4 13 19 22H 3 14 18H2 1 2H3 YKey NGTVDHYUFBKWID UHFFFAOYSA N Y verify Contents 1 History 2 Effects 3 See also 4 ReferencesHistory Edita Methylfentanyl was discovered by a team at Janssen Pharmaceutica in the 1960s 1 In 1976 it began to appear mixed with heroin as an additive and the mixture was sometimes also called 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 2 Over the next year there were 13 more deaths and eventually the responsible agent was identified as a methylfentanyl 3 A bag of China White a methylfentanyl a Methylfentanyl was placed on the U S Schedule I list in September 1981 only two years after its appearance on the street but already other analogs were being developed Following the appearance of a methylfentanyl on the market over ten new analogs of fentanyl have been reported starting with para fluorofentanyl followed by a methylacetylfentanyl then by the highly potent 3 methylfentanyl and subsequently by many others such as b hydroxyfentanyl ohmefentanyl b hydroxythiofentanyl and b hydroxy 4 methylfentanyl 4 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 new drug analogs individually as each appeared The chemical structure of fentanyl has been used as a basis in modern chemistry for the discovery and nomenclature of many new fentanyl analogues sometimes called fentalogs In 1991 a group of Russian chemistry students discovered a simplified synthesis route which used phosgene instead of phenethylamine 5 Soon abuse of the drug became widespread causing a tenth of overdoses in the Moscow region a Methylfentanyl became notorious for low safety and production declined citation needed Effects EditThis section needs more reliable medical references for verification or relies too heavily on primary sources Please review the contents of the section and add the appropriate references if you can Unsourced or poorly sourced material may be challenged and removed Find sources A Methylfentanyl news newspapers books scholar JSTOR November 2013 a 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 a methyl group interferes with binding to metabolic enzymes which break the drug down The independent discovery of the effect of the a methyl group on fentanyl also marked the first time clandestine recreational drug research had an effect on practical scientific research 6 Since fentanyl itself is highly potent and notorious for causing fatal overdoses when abused and also very short lasting with recreational users often administering doses every hour a methylfentanyl could have several advantages over the parent compound as a recreational drug Side effects of fentanyl analogs 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 Fentanyl analogs such as a methylfentanyl and 3 methylfentanyl are often used as the cut in small amounts in normal heroin stamps and bags making them more potent and profitable than when sold as heroin alone due to the advantage of raising the retail price and potency per unit sold See also Edit3 Methylbutyrfentanyl 3 Methylfentanyl 4 Fluorofentanyl Butyrfentanyl Furanylfentanyl List of fentanyl analoguesReferences Edit US Patent 3164600 Kram TC Cooper DA Allen AC 1981 Behind the identification of China White Analytical Chemistry 53 12 1379A 1386A doi 10 1021 ac00235a003 PMID 7294353 Gillespie TJ Gandolfi AJ Davis TP Morano RA 1982 Identification and quantification of alpha methylfentanyl in post mortem specimens Journal of Analytical Toxicology 6 3 139 142 doi 10 1093 jat 6 3 139 PMID 7109557 Henderson GL Designer Drugs Past History and Future Prospects 1988 Designer drugs Past history and future prospects Journal of Forensic Sciences 33 2 569 575 doi 10 1520 JFS11976J PMID 3286815 CHAZAN GUY May 27 1993 The trade in illegal narcotics looks set to mushroom United Press International Retrieved April 6 2017 Ohmefentanyl Retrieved from https en wikipedia org w index php title A Methylfentanyl amp oldid 1143748080, wikipedia, wiki, book, books, library,
