Utopioid (drug class)
Utopioids (U-type opioids) are a class of synthetic opioid analgesic drugs first developed in the 1970s by the pharmaceutical company Upjohn,[1] but never marketed for medical use, although some compounds from this class have been used for scientific research as model kappa opioid receptor agonists. In the mid-2010s, one mu opioid receptor selective compound from this class, U-47700, re-emerged as a designer drug and became widely sold around the world for several years before being banned in various jurisdictions from 2016 onwards. Following the banning of U-47700, a number of related compounds have continued to appear on illicit drug markets, typically sold over the internet or as components of mixtures sold as "street heroin". U-47700 itself is the most potent mu opioid agonist from this class, around 7-10x the potency of morphine. Some other compounds such as 3,4-MDO-U-47700 and N-Ethyl-U-47700 retain similar mu selectivity but with lower potency similar to that of morphine, or have a mixture of mu and kappa mediated effects, such as U-48800. Most utopioid derivatives are however selective kappa agonists, which may have limited abuse potential as dissociative hallucinogens, but do not alleviate withdrawal distress in opioid dependent individuals or maintain addiction in a typical sense. Nevertheless, this has not stopped them from being sold as designer drugs, and a number of these compounds are now banned in many jurisdictions alongside U-47700 itself.[2][3][4][5][6][7][8][9]
Table of Utopioids
Chemical structure | Drug name | PubChem | CAS number |
---|---|---|---|
U-47109 | 44269286 | 67579-13-9 | |
U-47700 | 13544016 | 82657-23-6 | |
U-47931E (Bromadoline) | 6328449 | 2418521-61-4 | |
U-48520 | 13544026 | 67579-11-7 | |
U-48800 | 137700072 | 2370977-17-4 | |
U-49900 | 129392412 | 67579-76-4 | |
U-50488 | 3036289 | 67198-13-4 | |
U-51574 | 44269303 | ||
U-62066 (Spiradoline) | 55652 | 87151-85-7 | |
U-69593 | 105104 | 96744-75-1 | |
U-77891 | 117071705 | 119878-31-8 | |
N-Desmethyl-U-47700 | 129390993 | 67579-73-1 | |
N,N-Didesmethyl-U-47700 | 129406364 | 2616858-81-0 | |
3,4-MDO-U-47700 | 139598237 | 2488874-96-8 | |
3,4-Ethylenedioxy-U-47700 | 137700298 | 2749619-08-5 | |
3,4-Ethylenedioxy-U-51574 | 137700374 | 2748623-91-6 | |
N-Ethyl-U-47700 | 155907846 | ||
N-Propyl-U-47700 | 137700434 | 2749433-76-7 | |
N-Isopropyl-U-47700 | 137700166 | 2748319-16-4 | |
N-Cyclopropyl-U-47700 | 165361451 | ||
N-Methoxy-U-47700 | 155907659 | ||
N-Methyl-U-47931E | 54482637 | 75570-38-6 | |
3,4-Dibromo-U-47700 | |||
3,4-Difluoro-U-47700 | 165362347 | 2417942-54-0 | |
2,4-Difluoro-U-48800 | |||
4-TFM-U-48520 (U-04) | 53720446 | 67579-38-8 | |
α-U10 | 165362154 | 2417942-61-9 | |
β-U10 | 54524276 | 67579-80-0 | |
References
- "Utopioids". Cayman Chemical News and Announcements. 12 July 2018.
- Armenian P, Vo KT, Barr-Walker J, Lynch KL (May 2018). "Fentanyl, fentanyl analogs and novel synthetic opioids: A comprehensive review". Neuropharmacology. 134 (Pt A): 121–132. doi:10.1016/j.neuropharm.2017.10.016. PMID 29042317. S2CID 21404877.
- Sharma KK, Hales TG, Rao VJ, NicDaeid N, McKenzie C (2019). "The search for the "next" euphoric non-fentanil novel synthetic opioids on the illicit drugs market: current status and horizon scanning". Forensic Toxicology. 37 (1): 1–16. doi:10.1007/s11419-018-0454-5. PMC 6314991. PMID 30636980.
- Kyei-Baffour K, Lindsley CW (December 2020). "DARK Classics in Chemical Neuroscience: U-47700". ACS Chemical Neuroscience. 11 (23): 3928–3936. doi:10.1021/acschemneuro.0c00330. PMID 32639714. S2CID 220438986.
- Baumann MH, Tocco G, Papsun DM, Mohr AL, Fogarty MF, Krotulski AJ (November 2020). "U-47700 and Its Analogs: Non-Fentanyl Synthetic Opioids Impacting the Recreational Drug Market". Brain Sciences. 10 (11): 895. doi:10.3390/brainsci10110895. PMC 7700279. PMID 33238449.
- Vandeputte MM, Persson M, Walther D, Vikingsson S, Kronstrand R, Baumann MH, Gréen H, Stove CP (March 2022). "Characterization of recent non-fentanyl synthetic opioids via three different in vitro µ-opioid receptor activation assays". Archives of Toxicology. 96 (3): 877–897. doi:10.1007/s00204-021-03207-9. PMID 35072756. S2CID 246239574.
- Otte L, Wilde M, Auwärter V, Grafinger KE (July 2022). "Investigation of the μ- and κ-opioid receptor activation by eight new synthetic opioids using the [35 S]-GTPγS assay: U-47700, isopropyl U-47700, U-49900, U-47931E, N-methyl U-47931E, U-51754, U-48520, and U-48800". Drug Testing and Analysis. 14 (7): 1187–1199. doi:10.1002/dta.3238. PMID 35142070. S2CID 246701889.
- "Non-fentanyl opioids and related new psychoactive substances with no known legitimate uses" (PDF). International Narcotics Control Board. 28 January 2022.
- Vandeputte MM, Stove CP (July 2023). "In vitro μ-opioid receptor activation potential of U10 and β-U10, positional isomers of the synthetic opioid naphthyl U-47700". Drug Testing and Analysis. doi:10.1002/dta.3554. PMID 37482925. S2CID 260101432.