Chemistry:Acrylfentanyl
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| Formula | C22H26N2O |
| Molar mass | 334.463 g·mol−1 |
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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.[1][2][3][4][5] 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.[6][7][8][9]
Side effects
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.[10]
As acrylamide derivatives are often used in drug discovery to make covalent inhibitors which will bind irreversibly to its target, acrylfentanyl is claimed to be naloxone resistant.[11] However, acute intoxications with acrylfentanyl on mice[12] threatened by naloxone (2 mg/kg) have shown that acrylfentanyl could be displaced from the opioid receptor.
Acrylfentanyl has been linked to 20 deaths in Sweden as well as two deaths in Denmark in summer 2016.[13][14]
Legal status
Acrylfentanyl is a Schedule I controlled substance in the United States.[15] As of 16 August 2016, it is an illegal medicine in Sweden.[16]
See also
- 3-Methylbutyrfentanyl
- 4-Fluorobutyrfentanyl
- 4-Methoxybutyrfentanyl
- Acetylfentanyl
- Butyrfentanyl
- Furanylfentanyl
- List of fentanyl analogues
References
- ↑ "Acrylfentanyl (hydrochloride)". Cayman Chemical. https://www.caymanchem.com/product/19312.
- ↑ "Acryloylfentanyl, a recently emerged new psychoactive substance: a comprehensive review". Forensic Toxicology 35 (2): 232–243. July 2017. doi:10.1007/s11419-017-0367-8.
- ↑ "Identification of a new psychoactive substance in seized material: the synthetic opioid N-phenyl-N-[1-(2-phenethyl)piperidin-4-ylprop-2-enamide (Acrylfentanyl)"]. Drug Testing and Analysis 9 (3): 415–422. March 2017. doi:10.1002/dta.2046. PMID 27476446.
- ↑ "New Psychoactive Substances (NPS) - the Hydra monster of recreational drugs". Clinical Toxicology 55 (1): 1–3. January 2017. doi:10.1080/15563650.2016.1217003. PMID 27549399.
- ↑ "In vitro and in vivo pharmaco-dynamic study of the novel fentanyl derivatives: Acrylfentanyl, Ocfentanyl and Furanylfentanyl". Neuropharmacology 209: 109020. May 2022. doi:10.1016/j.neuropharm.2022.109020. PMID 35247453.
- ↑ "Potential affinity labels for the opiate receptor based on fentanyl and related compounds". Journal of Medicinal Chemistry 25 (8): 913–919. August 1982. doi:10.1021/jm00350a006. PMID 6288945.
- ↑ "Using support vector classification for SAR of fentanyl derivatives". Acta Pharmacologica Sinica 26 (1): 107–112. January 2005. doi:10.1111/j.1745-7254.2005.00014.x. PMID 15659122.
- ↑ "Fentanyl analogues with a modified propanamido group as potential affinity labels: synthesis and in vivo activity". Die Pharmazie 54 (4): 307–308. April 1999. PMID 10234745.
- ↑ "[Studies on potent analgesics. I. Synthesis and analgesic activity of derivatives of fentanyl (author's transl)"] (in zh). Yao Xue Xue Bao = Acta Pharmaceutica Sinica 16 (3): 199–210. March 1981. PMID 6264735. http://www.yxxb.com.cn:8081/aps/CN/abstract/abstract13196.shtml.
- ↑ "Fentanyls: Are we missing the signs? Highly potent and on the rise in Europe". The International Journal on Drug Policy 26 (7): 626–631. July 2015. doi:10.1016/j.drugpo.2015.04.003. PMID 25976511.
- ↑ "PHDMC - Community Overdose Action Team Issues Alert". 1 February 2017. https://www.phdmc.org/news-releases-coat/133-community-overdose-action-team-issues-alert-2-feb-17.
- ↑ "Potential affinity labels for the opiate receptor based on fentanyl and related compounds". Journal of Medicinal Chemistry 25 (8): 913–919. August 1982. doi:10.1021/jm00350a006. PMID 6288945.
- ↑ "Akrylfentanyl narkotikaklassas" (in sv). Rättsmedicinalverket. 9 August 2016. http://rmv.se/index.php?id=433.
- ↑ "Farligt stof i omløb - mistanken rettes mod acryl fentanyl" (in da). mynewsdesk. 6 September 2016. https://www.mynewsdesk.com/dk/nordjyllands-politi/pressreleases/farligt-stof-i-omloeb-mistanken-rettes-mod-acryl-fentanyl-1547605.
- ↑ "Controlled Substances by DEA Drug Code Number". Drug Enforcement Administration. https://www.deadiversion.usdoj.gov/schedules/orangebook/d_cs_drugcode.pdf.
- ↑ "31 nya ämnen kan klassas som narkotika eller hälsofarlig vara" (in sv). Folkhälsomyndigheten. 21 June 2016. https://www.folkhalsomyndigheten.se/nyheter-och-press/nyhetsarkiv/2016/juni/31-nya-amnen-kan-klassas-som-narkotika-eller-halsofarlig-vara/.
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