alpha-Methylfentanyl
[CAS# 79704-88-4]

Identification

• Classification: Organic raw materials >> Heterocyclic compound >> Piperidines
• Name: alpha-Methylfentanyl
• Synonyms: N-phenyl-N-[1-(1-phenylpropan-2-yl)piperidin-4-yl]propanamide
• Molecular Formula: C₂₃H₃₀N₂O
• Molecular Weight: 350.50
• CAS Registry Number: 79704-88-4 (53757-42-9)
• SMILES: CCC(=O)N(C1CCN(CC1)C(C)CC2=CC=CC=C2)C3=CC=CC=C3

Properties

• Density: 1.082 g/cm³
• Boiling Point: 474±38 ºC
• Flash Point: 185.1±19.1 ºC

Safety Data

• Controlled Substance: DEA Drug Code Number: 9814

Discovory and Applicatios

α-Methylfentanyl is a synthetic opioid and analog of fentanyl that has potent analgesic effects. It gained notoriety in the 1970s and 1980s for having a high potential for abuse. The advent of α-methylfentanyl and similar compounds highlighted the challenges of controlling synthetic opioids due to their high potency and risk of overdose. α-Methylfentanyl was first synthesized in 1974 by chemists at Janssen Pharmaceutica, the company that originally developed fentanyl. The goal was to create an opioid with similar or enhanced analgesic properties but with a different pharmacological profile. By introducing a methyl group at the α position of the fentanyl molecule, its binding affinity and potency were altered. Like fentanyl, α-methylfentanyl has a phenylpiperidine structure that is critical to its analgesic effects, and the addition of a methyl group at the α position enhances potency and alters its interaction with opioid receptors.

α-Methylfentanyl was initially used for pain relief due to its high potency, estimated to be 200 times more potent than morphine. However, its use in clinical practice has been limited by concerns about its narrow therapeutic index and potential for respiratory depression.

Studies on α-methylfentanyl have helped to understand the structural requirements for opioid receptor interactions and high-affinity binding. These studies have provided insights for the design of other synthetic opioids and the development of treatments for opioid use disorder. Toxicological studies have focused on the acute and chronic effects of α-methylfentanyl, including its potential for respiratory depression and overdose. These studies highlight the importance of developing strategies to mitigate the risks associated with synthetic opioid use.

The potency of α-methylfentanyl has led to illicit drug manufacturing. It became a street drug in the late 1970s and 1980s, often sold under names such as "China White" or "synthetic heroin." Its high potency and difficulty in controlling dosage have led to numerous overdoses and deaths. The emergence of alpha-methylfentanyl on the illicit market highlights the challenges of regulating synthetic opioids. Its high potency and the fact that only small amounts are needed to produce significant effects complicates law enforcement efforts and increases the risk of accidental overdose.

Due to its high abuse potential and associated risks, alpha-methylfentanyl is classified as a Schedule I controlled substance in the United States and many other countries. This classification imposes strict regulations on its manufacture, distribution, and possession. In response to the emergence of new synthetic opioids such as alpha-methylfentanyl, the Federal Analogs Act of the United States allows substances similar to controlled drugs to be regulated, providing a legal framework to address the challenges posed by new synthetic compounds.

References

1981. The Bogus Drug: Three Methyl & Alpha Methyl Fentanyl Sold as �China White�. Journal of Psychoactive Drugs, 13(1).
DOI: 10.1080/02791072.1981.10471455

1982. Identification and Quantification of Alpha-Methylfentanyl in Post Mortem Specimens. Journal of Analytical Toxicology, 6(3).
DOI: 10.1093/jat/6.3.139

2021. Determination of Fentanyl, Alpha-Methylfentanyl, Beta-Hydroxyfentanyl and the Metabolite Norfentanyl in Rat Urine by LC�MS-MS. Journal of Analytical Toxicology, 45(7).
DOI: 10.1093/jat/bkab021