Chemistry:Utopioid (drug class)

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Utopioids (U-type opioids) are a class of synthetic opioid analgesic drugs first developed in the 1970s by the pharmaceutical company Upjohn.[1] However, they were never marketed for medical use. 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 prohibition of U-47700, a number of related compounds have continued to appear on illicit drug markets. They are often marketed online or included as components in mixtures sold under the guise of "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 structure.png U-47109 44269286 67579-13-9
U-47700 fixedstructure.svg U-47700 13544016 82657-23-6
U-47931E structure.png U-47931E (Bromadoline) 6328449 2418521-61-4
U-48520 structure.png U-48520 13544026 67579-11-7
U-48800 structure.png U-48800 137700072 2370977-17-4
U-49900 structure.png U-49900 129392412 67579-76-4
U-50488 structure.svg U-50488 3036289 67198-13-4
U-51574 structure.png U-51574 44269303
Spiradoline Structure.svg U-62066 (Spiradoline) 55652 87151-85-7
U-69,593 structure.svg U-69593 105104 96744-75-1
U-77891.svg U-77891 117071705 119878-31-8
N-Desmethyl-U-47700 structure.png N-Desmethyl-U-47700 129390993 67579-73-1
N,N-Didesmethyl-U-47700 structure.png N,N-Didesmethyl-U-47700 129406364 2616858-81-0
3,4-MDO-U-47700 structure.png 3,4-MDO-U-47700 139598237 2488874-96-8
3,4-Ethylenedioxy-U-47700 structure.png 3,4-Ethylenedioxy-U-47700 137700298 2749619-08-5
3,4-Ethylenedioxy-U-51574 structure.png 3,4-Ethylenedioxy-U-51574 137700374 2748623-91-6
N-Ethyl-U-47700 structure.png N-Ethyl-U-47700 155907846
N-Propyl-U-47700 structure.png N-Propyl-U-47700 137700434 2749433-76-7
N-Isopropyl-U-47700 structure.png N-Isopropyl-U-47700 137700166 2748319-16-4
N-Cyclopropyl-U-47700 structure.png N-Cyclopropyl-U-47700 165361451
N-Methoxy-U-47700 structure.png N-Methoxy-U-47700 155907659
N-Methyl-U-47931E structure.png N-Methyl-U-47931E 54482637 75570-38-6
3,4-Dibromo-U-47700 structure.png 3,4-Dibromo-U-47700
3,4-Difluoro-U-47700 structure.png 3,4-Difluoro-U-47700 165362347 2417942-54-0
2,4-Difluoro-U-48800 structure.png 2,4-Difluoro-U-48800
4-TFM-U-47700 structure.png 4-TFM-U-48520 (U-04) 53720446 67579-38-8
Alpha-U10 structure.png α-U10 165362154 2417942-61-9
Beta-U10 structure.png β-U10 54524276 67579-80-0

See also

References

  1. ↑ "Utopioids". Cayman Chemical News and Announcements. 12 July 2018. https://www.caymanchem.com/news/utopioids. 
  2. ↑ "Fentanyl, fentanyl analogs and novel synthetic opioids: A comprehensive review". Neuropharmacology 134 (Pt A): 121–132. May 2018. doi:10.1016/j.neuropharm.2017.10.016. PMID 29042317. https://escholarship.org/uc/item/8xh0s7nf. 
  3. ↑ "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. 2019. doi:10.1007/s11419-018-0454-5. PMID 30636980. 
  4. ↑ "DARK Classics in Chemical Neuroscience: U-47700". ACS Chemical Neuroscience 11 (23): 3928–3936. December 2020. doi:10.1021/acschemneuro.0c00330. PMID 32639714. 
  5. ↑ "U-47700 and Its Analogs: Non-Fentanyl Synthetic Opioids Impacting the Recreational Drug Market". Brain Sciences 10 (11): 895. November 2020. doi:10.3390/brainsci10110895. PMID 33238449. 
  6. ↑ "Characterization of recent non-fentanyl synthetic opioids via three different in vitro µ-opioid receptor activation assays". Archives of Toxicology 96 (3): 877–897. March 2022. doi:10.1007/s00204-021-03207-9. PMID 35072756. 
  7. ↑ "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. July 2022. doi:10.1002/dta.3238. PMID 35142070. 
  8. ↑ "Non-fentanyl opioids and related new psychoactive substances with no known legitimate uses.". International Narcotics Control Board. 28 January 2022. http://www.incb.org/documents/Global_Projects_OPIOIDS/INCB.GRIDS.OPIOIDS.NoFOs_list.pdf. 
  9. ↑ "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. July 2023. doi:10.1002/dta.3554. PMID 37482925. 



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