List of fentanyl analogues

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2,5-Dimethylfentanyl

Phenaridine (2,5-Dimethylfentanyl) is an opioid analgesic that is an analogue of fentanyl. It was developed in 1972, and is used for surgical anasthesia.

Systematic (IUPAC) name
N-[2,5-dimethyl-1-(2-phenylethyl)piperidin-4-yl]-N-phenylpropanamide

3-Allylfentanyl

3-Allylfentanyl is an opioid analgesic that is an analogue of fentanyl. 3-Allylfentanyl has similar effects to fentanyl. Side effects of fentanyl analogs are similar to those of fentanyl itself, which include itching, nausea and potentially serious respiratory depression, which can be life-threatening.

Systematic (IUPAC) name
N-[(3S,4R)-1-phenethyl-3-prop-2-enylpiperidin-4-yl]-N-phenylpropanamide

3-Methylbutyrfentanyl

3-Methylbutyrfentanyl (3-MBF) is an opioid analgesic that is an analog of butyrfentanyl. 3-Methylbutyrfentanyl is one of the most potent drugs that have been sold online as a designer drug.

p-fluoroisobutyrfentanyl

p-chloroisobutyrfentanyl

Cyclopentylfentanyl

Furanylethylfentanyl

Methoxyacetylfentanyl

Thenylfentanyl

3-Methylfentanyl

3-Methylfentanyl (3-MF, mefentanyl) is an opioid analgesic that is an analog of fentanyl. 3-Methylfentanyl is one of the most potent drugs that has been widely sold on the black market, estimated to be between 400 and 6000 times stronger than morphine, depending on which isomer is used (with the cis isomers being the more potent ones).

Systematic (IUPAC) name
(RS)-N-(3-methyl-1-phenethyl-4-piperidyl)-N-phenyl-propanamide

3-Methylthiofentanyl

3-Methyl-thiofentanyl was sold briefly on the black market in the early 1980s, before the introduction 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.

Systematic (IUPAC) name
(RS)-N-{3-methyl-1-[2-(2-thienyl)ethyl]piperidin-4-yl}-N-phenylpropanamide

4-Fluorobutyrfentanyl

4-Fluorobutyrfentanyl (also known as 4-FBF and p-FBF) is an opioid analgesic that is an analog of butyrfentanyl and has been sold online as a designer drug. It is closely related to 4-fluorofentanyl, which has an EC50 value of 4.2 nM for the human μ-opioid receptor.

Systematic (IUPAC) name
N-(4-Fluorophenyl)-N-[1-(2-phenylethyl)-4-piperidinyl]-butanamide

Parafluorofentanyl

Parafluorofentanyl (4-Fluorofentanyl) is an opioid analgesic being an analogue of fentanyl developed by Janssen Pharmaceutica in the 1960s.

Systematic (IUPAC) name
N-(4-fluorophenyl)-N-[1-(2-phenylethyl)piperidin-4-yl]propanamide

4-Phenylfentanyl

4-Phenylfentanyl is an opioid analgesic that is a derivative of fentanyl. It was developed during the course of research that ultimately resulted in super-potent opioid derivatives such as carfentanil, though it is a substantially less potent analogue. 4-Phenylfentanyl is around 8x the potency of fentanyl in analgesic tests on animals, but more complex 4-heteroaryl derivatives such as substituted thiophenes and thiazoles are more potent still, as they are closer bioisosteres to the 4-carbomethoxy group of carfentanil.

Systematic (IUPAC) name
N-phenyl-N-[4-phenyl-1-(2-phenylethyl)piperidin-4-yl]propanamide

Valerylfentanyl

4-Methoxybutyrfentanyl

4-Methoxybutyrfentanyl (also known as 4-MeO-BF) is an opioid analgesic that is an analog of butyrfentanyl and has been sold online as a designer drug.

Systematic (IUPAC) name
N-(4-Methoxyphenyl)-N-[1-(2-phenylethyl)-4-piperidinyl]-butanamide

Acrylfentanyl

Acrylfentanyl (also known as acryloylfentanyl) is a highly potent opioid analgesic that is an analog of fentanyl and has been sold online as a designer drug.

Systematic (IUPAC) name
N-Phenyl-N-[1-(2-phenylethyl)piperidin-4-yl]prop-2-enamide

α-Methylacetylfentanyl

α-Methylacetylfentanyl (or alphamethylacetylfentanyl) is an opioid analgesic that is an analog of fentanyl. It is a Schedule I controlled substance in the United States, with a DEA ACSCN of 9815.

Systematic (IUPAC) name
N-Phenyl-N-[1-(1-phenylpropan-2-yl)-4-piperidyl]acetamide

Alphamethylbutyrlfentanyl

α-Methylfentanyl

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

Systematic (IUPAC) name
N-phenyl-N-[1-(1-phenylpropan-2-yl)-4-piperidyl]propanamide

Alphamethylthiofentanyl

α-methyl-thiofentanyl is an opioid analgesic that is an analogue of fentanyl.

Systematic (IUPAC) name
N-phenyl-N-[1-(1-thiophen-2-ylpropan-2-yl)-4-piperidyl]propanamide

Acetylfentanyl

Acetylfentanyl (acetyl fentanyl) is an opioid analgesic drug that is an analog of fentanyl. Studies have estimated acetylfentanyl to be fifteen times more potent than morphine.[5][6] It has never been licensed for medical use and instead only been sold as a designer drug.

Systematic (IUPAC) name
N-(1-Phenethylpiperidin-4-yl)-N-phenylacetamide

Betahydroxyfentanyl

β-hydroxyfentanyl was sold briefly on the black market in the early 1980s, before the introduction 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.

Systematic (IUPAC) name
N-[1-(2-hydroxy-2-phenylethyl)piperidin-4-yl]-N-phenylpropanamide

Alfentanil

Alfentanil (R-39209, trade name Alfenta, Rapifen in Australia) is a potent but short-acting synthetic opioid analgesic drug, used for anaesthesia in surgery. It is an analogue of fentanyl with around 1/4 to 1/10 the potency of fentanyl and around 1/3 of the duration of action, but with an onset of effects 4x faster than fentanyl.

Systematic (IUPAC) name
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

Benzylfentanyl

Benzylfentanyl (R-4129) is a fentanyl analog.[1] It was temporarily placed in the US Schedule I by emergency scheduling in 1985 due to concerns about its potential for abuse as a designer drug, but this placement was allowed to expire and benzylfentanyl was formally removed from controlled substance listing in 2010, after the DEA’s testing determined it to be “essentially inactive” as an opioid.

IUPAC name
N-(1-Benzylpiperidin-4-yl)-N-phenylpropanamide

β-Methylfentanyl

β-Methylfentanyl was sold briefly on the black market in the early 1980s, before the introduction 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.

Systematic (IUPAC) name
N-{1-[2-hydroxy-2-(thiophen-2-yl)ethyl]piperidin-4-yl}-N-phenylpropanamide

Butyrfentanyl

Butyr-fentanyl or butyrylfentanyl (not to be confused with 3-methylfentanyl) is a potent short-acting synthetic opioid analgesic drug. It is an analogue of fentanyl with around one quarter the potency of fentanyl. One of the first mentions of this drug can be found in document written by The College on Problem of Drug Dependence, where it is mentioned as N-butyramide fentanyl analog

Systematic (IUPAC) name
N-(1-(2-phenylethyl)-4-piperidinyl)-N-phenylbutyramide

Brifentanil

Brifentanil (A-3331) is an opioid analgesic that is an analogue of fentanyl and was developed in the early 1990s.

Systematic (IUPAC) name
N-[(3R,4S)-1-[2-(4-ethyl-5-oxotetrazol-1-yl)ethyl] -3-methylpiperidin-4-yl]-N-(2-fluorophenyl)-2-methoxyacetamide

Carfentanil

Carfentanil or carfentanyl (also known as 4-carbomethoxyfentanyl) is an analog of the synthetic opioid analgesic fentanyl. It was found to be four orders of magnitude or 10,000 times more potent than morphine, making it one of the most potent known and the most potent commercially used opioids.

Systematic (IUPAC) name
4-((1-oxopropyl)-phenylamino)-1-(2-phenylethyl)-4-piperidinecarboxylic acid methyl ester

Isobutyrfentanyl

Furanylfentanyl

Furanylfentanyl (Fu-F) is an opioid analgesic that is an analog of fentanyl and has been sold as a designer drug. It has an ED50 value of 0.02 mg/kg in mice.[3] This makes it approximately five times less potent than fentanyl.

Systematic (IUPAC) name
N-Phenyl-N-[1-(2-phenylethyl)piperidin-4-yl]furan-2-carboxamide

Lofentanil

Lofentanil is one of the most potent opioid analgesics known and is an analogue of fentanyl, which was developed in 1960. It is most similar to the highly potent opioid carfentanil (4-carbomethoxyfentanyl), only slightly more potent. Lofentanil can be described as 3-methylcarfentanil, or 3-methyl-4-carbomethoxyfentanyl.

Systematic (IUPAC) name
methyl (3S,4R)-3-methyl-1-(2-phenylethyl)-4-[phenyl(propionyl)amino]piperidine-4-carboxylate

N-Methylcarfentanil

N-Methylcarfentanil (R-32395) is an opioid analgesic drug related to the highly potent animal tranquilizer carfentanil, but several thousand times weaker, being only slightly stronger than morphine. It was first synthesised by a team of chemists at Janssen Pharmaceutica led by Paul Janssen, who were investigating the structure-activity relationships of the fentanyl family of drugs.

Systematic (IUPAC) name
methyl 1-methyl-4-(N-phenylpropanamido)piperidine-4-carboxylate

Mirfentanil

Mirfentanil is a fentanyl derivative with strong selectivity for the μ opioid receptor. At lower doses, it antagonizes the analgesic effects of alfentanil and substitutes for naloxone in morphine-treated monkeys; however, it also reverses naloxone-precipitated withdrawal in pigeons trained to discriminate morphine from naloxone.

IUPAC name
N-[1-(2-phenylethyl)piperidin-4-yl]-N-pyrazin-2-yl-2-furamide

R-30490

R-30490 (also known as 4-Methoxymethylfentanyl) is an opioid analgesic related to the highly potent animal tranquilizer carfentanil, and with only slightly lower potency. It was first synthesised by a team of chemists at Janssen Pharmaceutica led by Paul Janssen, who were investigating the structure-activity relationships of the fentanyl family of drugs.

Systematic (IUPAC) name
N-[4-(methoxymethyl)-1-(2-phenylethyl)piperidin-4-yl]-N-phenylpropanamide

Ohmefentanyl

Ohmefentanyl (also known as β-hydroxy-3-methylfentanyl, OMFand RTI-4614-4)[1] is an extremely potent opioid analgesic drug which selectively binds to the µ-opioid receptor.

Systematic (IUPAC) name
N-[1-(2-hydroxy-2-phenylethyl)-3-methylpiperidin-4-yl]-N-phenylpropanamide

Ocfentanil

Ocfentanil (INN) (also called A-3217) is a potent synthetic opioid structurally related to fentanyl that was developed in the early 1990s as one of a series of potent naloxone-reversible opioids in an attempt to obtain an opioid that had better therapeutic indices in terms of cardiovascular effects and respiratory depression as compared to fentanyl.

Systematic (IUPAC) name
N-(2-Fluorophenyl)-2-methoxy-N-[1-(2-phenylethyl)piperidin-4-yl]acetamide

Remifentanil

Remifentanil (marketed by GlaxoSmithKline and Abbott as Ultiva[1]) is a potent, short-acting synthetic opioid analgesic drug. It is given to patients during surgery to relieve pain and as an adjunct to an anaesthetic. Remifentanil is used for sedation as well as combined with other medications for use in general anesthesia.

Systematic (IUPAC) name
methyl 1-(3-methoxy-3-oxopropyl)-4-(N-phenylpropanamido)piperidine-4-carboxylate

Sufentanil

Sufentanil (R30730, brand name Sufenta) is a synthetic opioid analgesic drug approximately five to 10 times more potent than its parent drug, fentanyl, and 500 times as potent as morphine.

Systematic (IUPAC) name
N-[4-(Methoxymethyl)-1-(2-thiofuran-2-ylethyl)-4-piperidyl]-N-phenylpropanamide

Thiofentanyl

Thiofentanyl is an opioid analgesic that is an analogue of fentanyl. Thiofentanyl was sold briefly on the black market in the early 1980s, before the introduction 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.

Systematic (IUPAC) name
N-phenyl-N-{1-[2-(2-thienyl)ethyl]piperidin-4-yl}propanamide

Trefentanil

Trefentanil (A-3665) is an opioid analgesic that is an analogue of fentanyl and was developed in 1992.

Systematic (IUPAC) name
N-{1-[2-(4-ethyl-5-oxo-4,5-dihydro-1H-tetrazol-1-yl)ethyl]-4-phenylpiperidin-4-yl}-N-(2-fluorophenyl)propanamide