α-Methylfentanyl

Source: Wikipedia, the free encyclopedia.
α-Methylfentanyl
Clinical data
Trade namesChina White
ATC code
  • none
Legal status
Legal status
Identifiers
  • N-phenyl-N-[1-(1-phenylpropan-2-yl)piperidin-4-yl]propanamide
JSmol)
  • O=C(N(c1ccccc1)C3CCN(C(Cc2ccccc2)C)CC3)CC
  • 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 checkY
  • Key:NGTVDHYUFBKWID-UHFFFAOYSA-N checkY
  (verify)

α-Methylfentanyl (or alpha-Methylfentanyl) an opioid analgesic that is an analog of fentanyl. It is sometimes sold as "China White".

History

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 sample of "China White"

α-Methylfentanyl was placed on the U.S.

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

α-Methylfentanyl has similar effects to

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

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.

See also

References

  1. ^ US Patent 3164600
  2. PMID 7294353
    .
  3. PMID 7109557
    .
  4. PMID 3286815
    .
  5. ^ CHAZAN, GUY (May 27, 1993). "The trade in illegal narcotics looks set to mushroom..." United Press International. Retrieved April 6, 2017.
  6. ^ Ohmefentanyl
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