List of fentanyl analogues
This is a list of fentanyl analogues, including both compounds developed by pharmaceutical companies for legitimate medical use, and those which have been sold as designer drugs and reported to national drug control agencies such as the DEA, or transnational agencies such as the EMCDDA and UNODC. This is not a comprehensive listing of fentanyl analogues, as more than 1400 compounds from this family have been described in the scientific and patent literature, but it includes all notable compounds that have reached late-stage human clinical trials, or which have been identified as having been sold as designer drugs.
In the United States, the Drug Enforcement Agency placed the broadly defined class of "Fentanyl-Related Substances" on the list of Schedule I drugs in 2018, making it illegal to manufacture, distribute, or possess fentanyl analogs.
Chemical structures of various fentanyl analoguesEdit
|Chemical structure||Common name|
|3-Methylfuranylfentanyl (3MFUF, TMFUF)|
|para-fluorofuranylfentanyl (p-F-Fu-F) [1802489-71-9]|
|Butyrfentanyl (Bu-F, BUF)|
|Hybrid molecule containing features of both fentanyl & haloperidol|
|Furanylfentanyl (Fu-F, FUF)|
|Fentanyl 4-methylene analogue (WO2007093603)|
Several jurisdictions have implemented analogue law controls of fentanyl analogues in an attempt to pre-emptively ban novel derivatives before they appear on the market. One representative example is the New Zealand provisions enacted in 1988 in response to the first wave of fentanyl derivatives. This bans a set of structures as follows;
"Fentanyl analogues, in which the N-[1-(2-phenethyl)-4-piperidyl]aniline nucleus has additional radicals, either alone or in combination, attached as follows:
(a) an acetyl, propionyl, butenoyl or butanoyl radical, attached to the aniline nitrogen atom:
(b) 1 or more alkyl radicals, with up to 10 carbon atoms in total, attached to the ethyl moiety:
(c) any combination of up to 5 alkyl radicals and/or alkoxy radicals (each with up to 6 carbon atoms, including cyclic radicals) and/or halogen radicals, attached to each of the benzene rings."
A more recent and somewhat broader example was introduced into US Federal legislation in 2018, covering the following structures;
"...fentanyl-related substances includes any substance not otherwise controlled in any schedule...that is structurally related to fentanyl by one or more of the following modifications:
- Replacement of the phenyl portion of the phenethyl group by any monocycle, whether or not further substituted in or on the monocycle;
- substitution in or on the phenethyl group with alkyl, alkenyl, alkoxyl, hydroxyl, halo, haloalkyl, amino or nitro groups;
- substitution in or on the piperidine ring with alkyl, alkenyl, alkoxyl, ester, ether, hydroxyl, halo, haloalkyl, amino or nitro groups;
- replacement of the aniline ring with any aromatic monocycle whether or not further substituted in or on the aromatic monocycle; and/or
- replacement of the N-propionyl group by another acyl group."
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- Drug Enforecement Administration, Department of Justice (2018). "Schedules of Controlled Substances:Temporary Placement of Fentanyl-Related Substances in Schedule I. Temporary amendment; temporary scheduling order". Federal Register. 83 (25): 5188–92. PMID 29932611.
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- "Schedules of Controlled Substances: Temporary Placement of Fentanyl-Related Substances in Schedule I". United States Federal Register.