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| Formula | C23H28N2O |
| Molar mass | 348.490 g·mol−1 |
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Crotonylfentanyl is an opioid analgesic that is an analog of fentanyl and structural isomer of cyclopropylfentanyl [1] and has been sold online as a designer drug. [2] [3] In December 2019, the UNODC announced scheduling recommendations placing crotonylfentanyl into Schedule I. [4]
Oxycodone, sold under various brand names such as Roxicodone and OxyContin, is a semi-synthetic opioid used medically for treatment of moderate to severe pain. It is highly addictive and is a commonly abused drug. It is usually taken by mouth, and is available in immediate-release and controlled-release formulations. Onset of pain relief typically begins within fifteen minutes and lasts for up to six hours with the immediate-release formulation. In the United Kingdom, it is available by injection. Combination products are also available with paracetamol (acetaminophen), ibuprofen, naloxone, naltrexone, and aspirin.
Fentanyl is a potent synthetic piperidine opioid drug primarily used as an analgesic. Fentanyl is 50 to 100 times more potent than morphine, and its primary clinical utility is in pain management for cancer patients and those recovering from painful surgeries. Fentanyl is also used as a sedative. Depending on the method of delivery, fentanyl can be very fast acting and ingesting a relatively small quantity can cause overdose. Fentanyl works by activating μ-opioid receptors. Fentanyl is sold under the brand names Actiq, Duragesic and Sublimaze, among others.
Carfentanil or carfentanyl, sold under the brand name Wildnil, is an extremely potent opioid analgesic which is used in veterinary medicine to anesthetize large animals such as elephants and rhinoceroses. It is typically administered in this context by tranquilizer dart. Carfentanil has also been used in humans for imaging of opioid receptors. It has additionally been used as a recreational drug, typically by injection, insufflation, or inhalation. Deaths have been reported in association with carfentanil.
Phenoperidine, is an opioid analgesic which is structurally related to pethidine and is used clinically as a general anesthetic.
Ocfentanil 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. Ocfentanil was never developed for medical use despite reasonable results in human clinical trials, but subsequently started to be sold as a designer drug starting in around 2013.
Butyrfentanyl or butyrylfentanyl is a potent short-acting synthetic opioid analgesic drug. It is an analog of fentanyl with around one quarter of its potency. 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. This document also states that the article describing its clinical effects was published in 1987. It is an agonist for the μ-opioid receptors.
U-47700, also known as U4, pink heroin, pinky, and pink, is an opioid analgesic drug developed by a team at Upjohn in the 1970s which has around 7.5 times the potency of morphine in animal models.
Acetylfentanyl is an opioid analgesic drug that is an analog of fentanyl. Studies have estimated acetylfentanyl to be 15 times more potent than morphine, which would mean that despite being somewhat weaker than fentanyl, it is nevertheless still several times stronger than pure heroin. It has never been licensed for medical use and instead has only been sold as a designer drug. Acetylfentanyl was discovered at the same time as fentanyl itself and had only rarely been encountered on the illicit market in the late 1980s. However, in 2013, Canadian police seized 3 kilograms of acetylfentanyl. As a μ-opioid receptor agonist, acetylfentanyl may serve as a direct substitute for heroin or other opioids. Common 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.
Aticaprant, also known by its developmental codes JNJ-67953964, CERC-501, and LY-2456302, is a κ-opioid receptor (KOR) antagonist which is under development for the treatment of major depressive disorder. A regulatory application for approval of the medication is expected to be submitted by 2025. Aticaprant is taken by mouth.
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. This makes it approximately one fifth as potent as fentanyl.
4-Fluorobutyrylfentanyl (also known as 4-FBF and p-FBF or para-fluorobutyrylfentanyl) 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.
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. In animal studies the IC50 (the half maximal inhibitory concentration for acrylfentanyl to displace naloxone) is 1.4 nM, being slightly more potent than fentanyl itself (1.6 nM) as well as having a longer duration of action.
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.
4-Fluoroisobutyrylfentanyl (also known as 4-FIBF and p-FIBF) is an opioid analgesic that is an analog of butyrfentanyl and structural isomer of 4-Fluorobutyrfentanyl 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. 4-fluoroisobutyrylfentanyl is a highly selective μ-opioid receptor agonist whose analgesic potency is almost ten times of that reported for morphine.
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.
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.
Tetramethylcyclopropylfentanyl is an opioid analgesic that is an analog of fentanyl and has been sold as a designer drug.
Brorphine is a piperidine-based opioid analgesic compound. Brorphine was originally discovered in a 2018 paper investigating functionally biased opioid compounds, with the intention of finding safer analgesics that produce less respiratory depression than typical opioids. Brorphine was originally reported to be highly biased, with an EC50 of 4.8nM for GTPγS binding and 182nM for β-arrestin recruitment, however a more recent study found no significant bias for any of the compounds tested, including brorphine. Its safety profile in any animal model has never been established. Despite the lack of safety information on the compound, brorphine has been sold as a designer drug since mid-2019, initially being identified in the US Midwest, though it has since been found in 2020 in Belgium. It is related in chemical structure to compounds such as benzylfentanyl and bezitramide, though it is sufficiently structurally distinct to fall outside the formal definition of a "fentanyl analogue" in jurisdictions such as the US and New Zealand which have Markush structure controls over this family of drugs.
