Alphamethylfentanyl

α-Methylfentanyl

Clinical data
ATC code	none
Legal status
Legal status	AU: S9 (Prohibited) CA: Schedule I DE: Anlage I (Controlled) UK: Class A US: Schedule I
Identifiers
IUPAC name N-phenyl-N-[1-(1-phenylpropan-2-yl)-4-piperidyl]propanamide
CAS Number	79704-88-4 Y
PubChem (CID)	62281
DrugBank	DB01557 Y
ChemSpider	56081 Y
UNII	8FU589W85C Y
Chemical and physical data
Formula	C23H30N2O
Molar mass	350.497 g/mol
3D model (Jmol)	Interactive image
SMILES O=C(N(c1ccccc1)C3CCN(C(Cc2ccccc2)C)CC3)CC
InChI 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 Y Key:NGTVDHYUFBKWID-UHFFFAOYSA-N Y

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

α-Methylfentanyl was initially discovered by a team at Janssen Pharmaceutica in the 1960s. 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. Over the next year there were 13 more deaths and eventually the responsible agent was identified as 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. 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.

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.