Valerylfentanyl
{{Short description|Opioid analgesic}}
{{Drugbox
| IUPAC_name = N-(1-(2-Phenylethyl)-4-piperidinyl)-N-phenylpentylamide
| image = Valerylfentanyl.png
| image2 = Valerylfentanyl 3D BS.png
| pregnancy_category =
| legal_AU =
| legal_BR = F1
| legal_CA = Schedule I
| legal_DE = Anlage II
| legal_UK = Class A
| legal_US = Schedule I
| legal_UN = N I
| legal_status =
| routes_of_administration =
| bioavailability =
| protein_bound =
| metabolism =
| elimination_half-life =
| excretion =
| CAS_number = 122882-90-0
| ATC_prefix =
| ATC_suffix =
| PubChem = 21595398
| KEGG = C22762
| DrugBank_Ref =
| DrugBank =
| ChemSpiderID = 10551383
| ChEBI_Ref =
| ChEBI =
| UNII_Ref =
| UNII = VUG0EQK700
| C=24 | H=32 | N=2 | O=1
| smiles = CCCCC(=O)N(C1CCN(CC1)CCC2=CC=CC=C2)C3=CC=CC=C3
| StdInChI = 1S/C24H32N2O/c1-2-3-14-24(27)26(22-12-8-5-9-13-22)23-16-19-25(20-17-23)18-15-21-10-6-4-7-11-21/h4-13,23H,2-3,14-20H2,1H3
| StdInChIKey = VCCPXHWAJYWQMR-UHFFFAOYSA-N
| synonyms =
}}
Valerylfentanyl is an opioid analgesic that is an analog of fentanyl and has been sold online as a designer drug.{{cite journal | vauthors = Cooman T, Hoover B, Sauvé B, Bergeron SA, Quinete N, Gardinali P, Arroyo LE | title = The metabolism of valerylfentanyl using human liver microsomes and zebrafish larvae | journal = Drug Testing and Analysis | volume = 14 | issue = 6 | pages = 1116–1129 | date = June 2022 | pmid = 35128825 | doi = 10.1002/dta.3233 | s2cid = 246633284 }} 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.{{cite journal | vauthors = Prekupec MP, Mansky PA, Baumann MH | title = Misuse of Novel Synthetic Opioids: A Deadly New Trend | journal = Journal of Addiction Medicine | volume = 11 | issue = 4 | pages = 256–265 | year = 2017 | pmid = 28590391 | pmc = 5537029 | doi = 10.1097/ADM.0000000000000324 }} In one study, it fully substituted for oxycodone and produced antinociception and oxycodone-like
discriminative stimulus effects comparable in potency to morphine in mice,{{cite journal | vauthors = Walentiny DM, Moisa LT, Beardsley PM | title = Oxycodone-like discriminative stimulus effects of fentanyl-related emerging drugs of abuse in mice | journal = Neuropharmacology | volume = 150 | pages = 210–216 | date = May 2019 | pmid = 30735691 | doi = 10.1016/j.neuropharm.2019.02.007 | doi-access = free }} but failed to stimulate locomotor activity in mice at doses up to 100 mg/kg.{{cite journal | vauthors = Varshneya NB, Walentiny DM, Moisa LT, Walker TD, Akinfiresoye LR, Beardsley PM | title = Opioid-like antinociceptive and locomotor effects of emerging fentanyl-related substances | journal = Neuropharmacology | volume = 151 | pages = 171–179 | date = June 2019 | pmid = 30904478 | pmc = 8992608 | doi = 10.1016/j.neuropharm.2019.03.023 | s2cid = 84182661 }}
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.{{cite journal | vauthors = Mounteney J, Giraudon I, Denissov G, Griffiths P | title = Fentanyls: Are we missing the signs? Highly potent and on the rise in Europe | journal = The International Journal on Drug Policy | volume = 26 | issue = 7 | pages = 626–631 | date = July 2015 | pmid = 25976511 | doi = 10.1016/j.drugpo.2015.04.003 }} 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.{{cite journal | vauthors = Armenian P, Vo KT, Barr-Walker J, Lynch KL | title = Fentanyl, fentanyl analogs and novel synthetic opioids: A comprehensive review | journal = Neuropharmacology | volume = 134 | issue = Pt A | pages = 121–132 | date = May 2018 | pmid = 29042317 | doi = 10.1016/j.neuropharm.2017.10.016 | s2cid = 21404877 | url = https://escholarship.org/uc/item/8xh0s7nf | url-access = subscription }}
Legal status
Valerylfentanyl is a Schedule I controlled drug in the USA since 1 February 2018.{{cite news|title=Schedules of Controlled Substances: Temporary Placement of Seven Fentanyl-Related Substances in Schedule I|url=https://www.federalregister.gov/documents/2018/02/01/2018-02008/schedules-of-controlled-substances-temporary-placement-of-seven-fentanyl-related-substances-in|newspaper=Federal Register|date=1 February 2018}}
In December of 2019, the UNODC announced scheduling recommendations placing valerylfentanyl into Schedule I.{{cite web|url=https://www.unodc.org/LSS/Announcement/Details/021820a0-8746-42a4-9ee3-47ce50b30ca3|title=December 2019 – WHO: World Health Organization recommends 12 NPS for scheduling}}