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| Formula | C22H26F2N2O |
| Molar mass | 372.460 g·mol−1 |
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2,2'-Difluorofentanyl is an opioid analgesic that is an analog of fentanyl which has been sold as a designer drug. [2]
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. Fentanyl analogs have killed hundreds of people throughout Europe and the former Soviet republics since the most recent resurgence in use began in Estonia in the early 2000s, and novel derivatives continue to appear. [3] A new wave of fentanyl analogues and associated deaths began in around 2014 in the US, and have continued to grow in prevalence; especially since 2016 these drugs have been responsible for hundreds of overdose deaths every week. [4]
As a ring-substituted derivative of fentanyl, 2,2'-difluorofentanyl is banned under drug analog laws in the United States [1] and other jurisdictions around the world.[ citation needed ]
β-Methylfentanyl is an opioid analgesic that is an analogue of fentanyl.
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 eight times 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.
R-30490 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. R-30490 was found to be the most selective agonist for the μ-opioid receptor out of all the fentanyl analogues tested, but it has never been introduced for medical use in humans, although the closely related drug sufentanil is widely used for analgesia and anesthesia during major surgery.
Benzylfentanyl (R-4129) is a fentanyl analog. 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. Benzylfentanyl has a Ki of 213 nM at the mu opioid receptor, binding around 1/200 as strong as fentanyl itself, though it is still slightly more potent than codeine.
3-Methylbutyrfentanyl (3-MBF) is an opioid analgesic that is an analog of butyrfentanyl.
Methoxyacetylfentanyl, commonly known as MAF is an opioid analgesic that is an analog of fentanyl and has been sold online as a designer drug.
Tetrahydrofuranylfentanyl is an opioid analgesic that is an analog of fentanyl and has been sold online as a designer drug, first appearing in Europe in late 2016.
Orthofluorofentanyl is an opioid analgesic that is an analog of fentanyl and has been sold online as a designer drug. While the structural isomer p-fluorofentanyl was one of the first illicit fentanyl analogues identified in 1981, Orthofluorofentanyl did not appear on the illicit market until August 2016.
Cyclopentylfentanyl is an opioid analgesic that is an analog of fentanyl and has been sold online as a designer drug, mainly in Sweden and other Scandinavian countries.
Valerylfentanyl is an opioid analgesic that is an analog of fentanyl and has been sold online as a designer drug. It has been seldom reported on illicit markets and there is little information about it, though it is believed to be less potent than butyrfentanyl but more potent than benzylfentanyl. In one study, it fully substituted for oxycodone and produced antinociception and oxycodone-like discriminative stimulus effects comparable in potency to morphine in mice, but failed to stimulate locomotor activity in mice at doses up to 100 mg/kg.
Isobutyrylfentanyl is an opioid analgesic that is an analog of fentanyl and has been sold online as a designer drug. It is believed to be around the same potency as butyrfentanyl but has been less widely distributed on illicit markets, though it was one of the earliest of the "new wave" of fentanyl derivatives to appear, and was reported in Europe for the first time in December 2012.
4-Chloroisobutyrylfentanyl is an opioid analgesic that is an analog of fentanyl, and has been sold online as a designer drug.
Cyclopropylfentanyl is an opioid analgesic that is an analog of fentanyl and has been sold as a designer drug. Between June and December 2017, a total of 78 cyclopropylfentanyl-related deaths with analytical confirmation in post-mortem samples were reported by various European countries. Another 115 deaths involving cyclopropylfentanyl were reported from the United States in 2017.
Benzoylfentanyl, also known as phenylfentanyl, is an opioid analgesic that is an analog of fentanyl and has been sold as a designer drug. In the United States, benzoylfentanyl was first identified in Drug Enforcement Administration drug seizures in 2018.
Tetramethylcyclopropylfentanyl is an opioid analgesic that is an analog of fentanyl and has been sold as a designer drug.
Benzodioxolefentanyl is an opioid analgesic that is an analog of fentanyl and has been sold as a designer drug.
3-Phenylpropanoylfentanyl (β'-phenylfentanyl) is an opioid analgesic that is an analog of fentanyl, which was invented in 1981, and has been sold as a designer drug, first identified in March 2017 in Sweden.
4-Methylphenethylacetylfentanyl is an opioid analgesic that is an analog of fentanyl and has been sold as a designer drug.
Isofentanyl (3-methyl-benzylfentanyl) is an opioid analgesic that is an analog of fentanyl first invented in 1973, and which has been sold as a designer drug.
4-Bromofentanyl (para-bromofentanyl) is an opioid analgesic drug that is an analog of fentanyl and has been sold as a designer drug, first identified in Pennsylvania in the US in March 2020.