List of fentanyl analogues

From Wikipedia, the free encyclopedia

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.[1][2][3][4][5][6] 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,[7][8][9][10][11] 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 Administration 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.[12]

Chemical structures of various fentanyl analogues[]

Chemical structure Common name Chemical name CAS number
Phenaridine.svg 2,5-Dimethylfentanyl N-[2,5-Dimethyl-1-(2-phenylethyl)piperidin-4-yl]-N-phenylpropanamide 42045-97-6
2,2'-Difluorofentanyl structure.png 2,2'-Difluorofentanyl N-(2-Fluorophenyl)-N-[1-(2-[2-fluorophenyl]ethyl)-4-piperidinyl]-propanamide
3-allylfentanyl.svg 3-Allylfentanyl N-[(3S,4R)-1-Phenethyl-3-prop-2-enylpiperidin-4-yl]-N-phenylpropanamide 82208-84-2
Nfepp.png 3-Fluorofentanyl (NFEPP) N-(3-Fluoro-1-phenethylpiperidin-4-yl)-N-phenylpropionamide 1422952-84-8
3-Furanylfentanyl structure.png 3-Furanylfentanyl (3FUF) N-Phenyl-N-[1-(2-phenylethyl)piperidin-4-yl]furan-3-carboxamide 101343-82-2
3-Methylbutyrfentanyl structure.png 3-Methylbutyrfentanyl N-[3-Methyl-1-(2-phenylethyl)piperidin-4-yl]-N-phenylbutanamide 97605-09-9
3-Methylfentanyl.svg 3-Methylfentanyl (3-MF) N-(3-methyl-1-phenethyl-4-piperidyl)-N-phenyl-propanamide 42045-86-3
3-Methylfuranylfentanyl structure.png 3-Methylfuranylfentanyl[13] (3MFUF, TMFUF) N-Phenyl-N-[3-methyl-1-(2-phenylethyl)piperidin-4-yl]furan-2-carboxamide
3-Methylthiofentanyl.svg 3-Methylthiofentanyl N-{3-Methyl-1-[2-(2-thienyl)ethyl]piperidin-4-yl}-N-phenylpropanamide 86052-04-2
3-Phenylpropanoylfentanyl structure.png 3-Phenylpropanoylfentanyl N-Phenyl-N-[1-(2-phenylethyl)piperidin-4-yl]-3-phenylpropanamide 79279-02-0
4-Fluorobutyrfentanyl.png 4-Fluorobutyrfentanyl (4-FBF) N-(4-Fluorophenyl)-N-[1-(2-phenylethyl)-4-piperidinyl]-butanamide 244195-31-1
PCl-IBF structure.png 4-Chloroisobutyrylfentanyl (4-CIBF) [14] 2-Methyl-N-(4-chlorophenyl)-N-[1-(1-phenylpropan-2-yl)piperidin-4-yl]propanamide 244195-34-4
4-Fluoroisobutyrfentanyl.svg 4-Fluoroisobutyrfentanyl (4-FIBF) N-(4-Fluorophenyl)-N-[1-(2-phenylethyl)-4-piperidinyl]-isobutanamide 244195-32-2
Parafluorofentanyl.svg 4-Fluorofentanyl N-(4-fluorophenyl)-N-[1-(2-phenylethyl)piperidin-4-yl]propanamide 90736-23-5
Parafluorofuranylfentanyl structure.png para-fluorofuranylfentanyl[15] (p-F-Fu-F) N-(1-phenethylpiperidin-4-yl)-N-(4-fluorophenyl)furan-2-carboxamide 1802489-71-9
Parachlorofuranylfentanyl structure.png para-chlorofuranylfentanyl (p-Cl-Fu-F) N-(1-phenethylpiperidin-4-yl)-N-(4-chlorophenyl)furan-2-carboxamide
Orthomethylfuranylfentanyl structure.png ortho-methylfuranylfentanyl (o-Me-Fu-F) N-(1-phenethylpiperidin-4-yl)-N-(o-tolyl)furan-2-carboxamide
Orthomethoxyfuranylfentanyl structure.png ortho-methoxyfuranylfentanyl (o-MeO-Fu-F) N-(1-phenethylpiperidin-4-yl)-N-(2-methoxyphenyl)furan-2-carboxamide
Orthoisopropylfuranylfentanyl structure.png ortho-isopropylfuranylfentanyl (o-iPr-Fu-F) N-(1-phenethylpiperidin-4-yl)-N-(2-isopropylphenyl)furan-2-carboxamide
4-Phenylfentanyl.png 4-Phenylfentanyl N-Phenyl-N-[4-phenyl-1-(2-phenylethyl)piperidin-4-yl]propanamide 120448-97-7
4-Methoxybutyrfentanyl.svg 4-Methoxybutyrfentanyl N-(4-Methoxyphenyl)-N-[1-(2-phenylethyl)-4-piperidinyl]-butanamide 2088842-68-4
4-Hydroxybutyrfentanyl structure.png para-Hydroxy‐butyrylfentanyl [16] N-(4-hydroxyphenyl)-N-[1-(2-phenylethyl)-4-piperidinyl]-butanamide
4-Methylphenethylacetylfentanyl structure.png 4-Methylphenethylacetylfentanyl[17] N-[1-[2-(4-Methylphenyl)ethyl]-4-piperidinyl]-N-phenylacetamide 1071703-95-1
Acrylfentanyl.svg Acrylfentanyl N-Phenyl-N-[1-(2-phenylethyl)piperidin-4-yl]prop-2-enamide 82003-75-6
Alphamethylacetylfentanyl.svg α-Methylacetylfentanyl N-Phenyl-N-[1-(1-phenylpropan-2-yl)-4-piperidyl]acetamide 101860-00-8
Alphamethylbutyrfentanyl structure.png α-Methylbutyrfentanyl N-phenyl-N-[1-(1-phenylpropan-2-yl)-4-piperidyl]butanamide 244195-36-6
Alphamethylfentanyl.svg α-Methylfentanyl (AMF) N-phenyl-N-[1-(1-phenylpropan-2-yl)-4-piperidyl]propanamide 79704-88-4
Alphamethylthiofentanyl.svg α-Methylthiofentanyl N-Phenyl-N-[1-(1-thiophen-2-ylpropan-2-yl)-4-piperidyl]propanamide 103963-66-2
Alphamethylbetahydroxyfentanyl structure.png α-Methyl-β-hydroxyfentanyl[18] N-[1-(1-hydroxy-1-phenylpropan-2-yl)piperidin-4-yl]-N-phenylpropanamide
Acetylfentanyl.svg Acetylfentanyl N-(1-Phenethylpiperidin-4-yl)-N-phenylacetamide 3258-84-2
Alfentanil-2D-skeletal.svg Alfentanyl N-{1-[2-(4-ethyl-5-oxo-4,5-dihydro-1H-1,2,3,4-tetrazol-1-yl)ethyl]-4-(methoxymethyl)piperidin-4-yl}-N-phenylpropanamide 71195-58-9
Benzodioxolefentanyl structure.png Benzodioxolefentanyl[19] N-Phenyl-N-[1-(2-phenylethyl)piperidin-4-yl]-2H-1,3-benzodioxole-5-carboxamide 2306823-01-6
Benzoylfentanyl structure.png Benzoylfentanyl N-(1-Phenethylpiperidin-4-yl)-N-phenylbenzamide 2309383-15-9
Benzylfentanyl.svg Benzylfentanyl N-(1-Benzylpiperidin-4-yl)-N-phenylpropanamide 1474-02-8
Betahydroxyfentanyl.svg β-Hydroxyfentanyl N-[1-(2-Hydroxy-2-phenylethyl)piperidin-4-yl]-N-phenylpropanamide 78995-10-5
Betahydroxythiofentanyl.svg β-Hydroxythiofentanyl N-{1-[2-Hydroxy-2-(thiophen-2-yl)ethyl]piperidin-4-yl}-N-phenylpropanamide 1474-34-6
Beta-hydroxy-4-methylfentanyl structure.png β-Hydroxy-4-methylfentanyl N-[1-(2-hydroxy-2-phenylethyl)-4-methylpiperidin-4-yl]-N-phenylpropanamide
Betamethylfentanyl.svg β-Methylfentanyl N-Phenyl-N-[1-(2-phenylpropyl)piperidin-4-yl]propanamide 79146-56-8
Brorphine Structure.png Brorphine[20] 1-{1-[1-(4-bromophenyl)ethyl]piperidin-4-yl}-1,3-dihydro-2H-benzimidazol-2-one 2244737-98-0
Butyrfentanyl.png Butyrfentanyl (Bu-F, BUF) N-(1-(2-Phenylethyl)-4-piperidinyl)-N-phenylbutyramide 1169-70-6
Brifentanil Structural Formulae.png Brifentanyl N-[(3R,4S)-1-[2-(4-Ethyl-5-oxotetrazol-1-yl)ethyl] -3-methylpiperidin-4-yl]-N-(2-fluorophenyl)-2-methoxyacetamide 101345-71-5
Carfentanil.svg Carfentanyl Methyl 1-(2-phenylethyl)-4-[phenyl(propanoyl)amino]piperidine-4-carboxylate 59708-52-0
Crotonylfentanyl Structure.png Crotonylfentanyl N-Phenyl-N-[1-(2-phenylethyl)-4-piperidinyl]-2-butenamide 760930-59-4
Cyclopentyl-F structure.png Cyclopentylfentanyl N-phenyl-N-[1-(2-phenylethyl)piperidin-4-yl]cyclopentanecarboxamide 2088918-01-6
Cyclobutylfentanyl structure.png Cyclobutylfentanyl [21] N-[1-(2-Phenylethyl)piperidin-4-yl]-N-phenylcyclobutanecarboxamide
Cyclopropylfentanyl structure.png Cyclopropylfentanyl N-[1-(2-Phenylethyl)piperidin-4-yl]-N-phenylcyclopropanecarboxamide 1169-68-2
Molecular Structure of Psychofentanil (EAZ-91-5).png EAZ-91-05 (quinuclidin-3-yl) 4-[phenyl(propanoyl)amino]-1-[2-(indol-3-yl)ethyl]piperidine-4-carboxylate
Isobutyrfentanyl structure.png Isobutyrylfentanyl 2-methyl-N-phenyl-N-[1-(1-phenylpropan-2-yl)piperidin-4-yl]propanamide 119618-70-1
Isofentanyl structure.png Isofentanyl N-(1-Benzyl-3-methylpiperidin-4-yl)-N-phenylpropanamide 79278-40-3
Homofentanyl structure.png Homofentanyl (N-phenylpropylnorfentanyl) [22] N-phenyl-N-[1-(3-phenylpropyl)piperidin-4-yl]propanamide 59708-54-2
Haloperidol-like fentanyl analogue.png Hybrid neuroleptanalgesic containing features of both fentanyl & haloperidol[23] N-phenyl-N-{1-[4-(4-fluorophenyl)-4-oxobutyl]piperidin-4-yl}propanamide
Tranyltanyl.png trans-phenylcyclopropyl-norfentanyl 1-(trans-2-Phenylcyclopropyl)-4-(N-propionylanilino)piperidine. 102504-49-4
Fentroline.png Pyridylfentany[24] N-phenyl-N-[1-(2-pyridin-4-ylethyl)piperidin-4-yl]propanamide 1443-41-0
Furanylfentanyl.svg Furanylfentanyl (Fu-F, FUF) N-Phenyl-N-[1-(2-phenylethyl)piperidin-4-yl]furan-2-carboxamide 101345-66-8
Furanylfentanyl2 structure.png Furanylethylfentanyl (FUEF) N-[1-[2-(2-furanyl)ethyl]-4-piperidinyl]-N-phenyl-propanamide 802544-02-1
Homofentanyl.png Fentanyl 4-methylene analogue (WO 2007/093603) N-phenyl-N-{[1-(2-phenylethyl)piperidin-4-yl]methyl}propanamide
IQMF-4 structure.png IQMF-4[25] N-[1-(2-Phenylethyl)piperidin-4-yl]-N-(1-phenylpyrazol-3-yl)prop-2-enamide
Lofentanil.svg Lofentanyl methyl (3S,4R)-3-methyl-1-(2-phenylethyl)-4-[phenyl(propionyl)amino]piperidine-4-carboxylate 61380-40-3
N-methylcarfentanil structure.png N-Methylnorcarfentanyl methyl 1-methyl-4-(N-phenylpropanamido)piperidine-4-carboxylate 59708-50-8
Methoxyacetylfentanyl structure.png Methoxyacetylfentanyl (MAF) 2-Methoxy-N-(1-phenethylpiperidin-4-yl)-N-phenylacetamide 101345-67-9
Metafluorofentanyl structure.png meta-fluorofentanyl N-(3-Fluorophenyl)-N-[1-(2-phenylethyl)-4-piperidinyl]-propanamide 90736-22-4
Mirfentanil.png Mirfentanyl N-[1-(2-Phenylethyl)piperidin-4-yl]-N-pyrazin-2-yl-2-furamide 117523-47-4
MP135 structure.png MP135[26] N-[4-{[2-(3-fluorophenyl)ethyl]carboxamido}-1-(2-phenylethyl)piperidin-4-yl]-N-benzylpropanamide
MDA-fentanyl structure.png N-(MDA)-fentanyl[27] N-(1-(1-(benzo[d][1,3]dioxol-5-yl)propan-2-yl)piperidin-4-yl)-N-phenylpropionamide
N-(2C-B)-fentanyl structure.png N-(2C-B)-fentanyl N-(1-(2-(2,5-dimethoxy-4-bromophenyl)ethyl)piperidin-4-yl)-N-phenylpropionamide
Ocfentanil.png Ocfentanyl N-(2-Fluorophenyl)-2-methoxy-N-[1-(2-phenylethyl)piperidin-4-yl]acetamide 101343-69-5
Ohmefentanyl.svg Ohmefentanyl N-[1-(2-hydroxy-2-phenylethyl)-3-methylpiperidin-4-yl]-N-phenylpropanamide 78995-14-9
Orthofluorofentanyl structure.png Orthofluorofentanyl N-(2-Fluorophenyl)-N-[1-(2-phenylethyl)-4-piperidinyl]-propanamide 910616-29-4
O-FIBF structure.png ortho-Fluoroisobutyrylfentanyl N-(2-Fluorophenyl)-N-[1-(2-phenylethyl)-4-piperidinyl]-2-methylpropanamide 2351142-33-9
Parafluoroisobutyrylbenzylfentanyl structure.png Parafluoroisobutyrylbenzylfentanyl N-[(1-benzylpiperidin-4-yl)methyl]-N-(4-fluorophenyl)-2-methylpropanamide
Pyrrolefentanyl Structure.png Pyrrole-fentanyl [28] N-[1-(2-Phenylethyl)piperidin-4-yl]-N-pyrrol-1-ylpropanamide
R-30490 structure.png R-30490 N-[4-(Methoxymethyl)-1-(2-phenylethyl)piperidin-4-yl]-N-phenylpropanamide 60618-49-7
Remifentanil2DCSDS.svg Remifentanyl methyl 1-(3-methoxy-3-oxopropyl)-4-(N-phenylpropanamido)piperidine-4-carboxylate 132875-61-7
RR49 structure.png RR49 [29] N-{1-[2-Fluoro-2-(2-fluorophenyl)ethyl]piperidin-4-yl}-N-phenylpropanamide
Secofentanyl structure.png Secofentanyl[30] N-phenyl-N-{4-[methyl(2-phenylethyl)amino]butan-2-yl}propanamide
Senecioylfentanyl structure.png Senecioylfentanyl [31] N-phenyl-N-[1-(2-phenylethyl)-4-piperidinyl]-3-methylbut-2-enamide
Sufentanil.svg Sufentanil N-[4-(Methoxymethyl)-1-(2-thiofuran-2-ylethyl)-4-piperidyl]-N-phenylpropanamide 56030-54-7
Tetrahydrofuranylfentanyl structure.png Tetrahydrofuranylfentanyl N-Phenyl-N-[1-(2-phenylethyl)piperidin-4-yl]oxolane-2-carboxamide 2142571-01-3
Tetramethylcyclopropylfentanyl structure.png Tetramethylcyclopropylfentanyl[32] 2,2,3,3-Tetramethyl-N-(1-phenethylpiperidin-4-yl)-N-phenylcyclopropane-1-carboxamide 2309383-11-5
Thenylfentanyl.svg Thenylfentanyl N-phenyl-N-{[1-(thiophen-2-ylmethyl)piperidin-4-yl]methyl}propanamide 117332-93-1
Formel von A-3080.png Thiafentanil methyl 4-(N-(2-methoxyacetyl)anilino)-1-(2-thiophen-2-ylethyl)piperidine-4-carboxylate 101345-60-2
Thiofentanyl.svg Thiofentanyl N-phenyl-N-{1-[2-(2-thienyl)ethyl]piperidin-4-yl}propanamide 1165-22-6
Trefentanil.png Trefentanyl N-{1-[2-(4-ethyl-5-oxo-4,5-dihydro-1H-tetrazol-1-yl)ethyl]-4-phenylpiperidin-4-yl}-N-(2-fluorophenyl)propanamide 120656-93-1
Trifluorofentanyl Structure.png Trifluorofentanyl [33] N-(3,4-difluorophenyl)-N-[1-(2-[4-fluorophenyl]ethyl)-4-piperidinyl]-propanamide
3,4-dichloro-4-MeO Fentanyl Structure.svg 3,4-dichloro-4''-methoxyfentanyl N-(3,4-dichlorophenyl)-N-[1-(2-[4-methoxyphenyl]ethyl)-4-piperidinyl]-propanamide
Valerylfentanyl.png Valerylfentanyl (VF) N-(1-(2-Phenylethyl)-4-piperidinyl)-N-phenylpentylamide 122882-90-0

Analogue controls[]

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."[34]

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:

  1. Replacement of the phenyl portion of the phenethyl group by any monocycle, whether or not further substituted in or on the monocycle;
  2. substitution in or on the phenethyl group with alkyl, alkenyl, alkoxyl, hydroxyl, halo, haloalkyl, amino or nitro groups;
  3. substitution in or on the piperidine ring with alkyl, alkenyl, alkoxyl, ester, ether, hydroxyl, halo, haloalkyl, amino or nitro groups;
  4. replacement of the aniline ring with any aromatic monocycle whether or not further substituted in or on the aromatic monocycle; and/or
  5. replacement of the N-propionyl group by another acyl group."[35]

See also[]

  • 25-NB
  • Arylcyclohexylamine
  • List of benzimidazole opioids
  • List of phenyltropanes
  • Structural scheduling of synthetic cannabinoids
  • Substituted cathinone

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