α-Methylfentanyl

From Wikipedia, the free encyclopedia
  (Redirected from Alphamethylfentanyl)
Jump to: navigation, search
α-Methylfentanyl
Alphamethylfentanyl.svg
Systematic (IUPAC) name
N-phenyl-N-[1-(1-phenylpropan-2-yl)-4-piperidyl]propanamide
Clinical data
Legal status Schedule 9 (Prohibited) (AU) Schedule I (US)
Identifiers
CAS number 79704-88-4 YesY
ATC code None
PubChem CID 62281
DrugBank DB01557
ChemSpider 56081 YesY
Chemical data
Formula C23H30N2O 
Mol. mass 350.497 g/mol
 YesY (what is this?)  (verify)

α-Methylfentanyl (or alpha-Methylfentanyl) is an opioid analgesic that is an analog of fentanyl.

History[edit]

α-Methylfentanyl was initially discovered by a team at Janssen Pharmaceutica in the 1960s.[1] In 1976 it began to appear 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.[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 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 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 each drug individually as they appeared.

In 1991, a group of Russian chemistry students discovered a unique synthesis route. 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[edit]

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.[5] 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. China White is anywhere from 10-1000 times more potent than heroin.[citation needed]

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 much more potent and profitable when sold as heroin alone due to the advantage of raising the retail price per unit sold.

References[edit]

  1. ^ US Patent 3164600
  2. ^ 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. 
  3. ^ 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. 
  4. ^ 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. PMID 3286815. 
  5. ^ Ohmefentanyl