R6890
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| Other names | Spirochlorphine |
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| Formula | C21H24ClN3O |
| Molar mass | 369.89 g·mol−1 |
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R6890, sometimes known as spirochlorphine, is an opioid analgesic and a member of the spiropiperidine family of agents.[1][2][3] The first known mention of this compound was in 1977.[4] Other examples of agents from this class are Ro64-6198 and Ro65-6570. Brorphine also has a similar structure. It has been sold as a designer drug, and was proposed for placement on the Schedule 1 list in the USA on 1 July 2026.[5]
A precursor chemical used in the synthesis of R6890 is 1-phenyl-1,3,8-triazaspiro(4,5)decan-4-one (also known as spirodecanone), which is used in the synthesis of other drugs including spirilene, fluspirilene, spiramide, spiperone, RP-23618, spiroxatrine, L008716 and R5260.
Pharmacology
[edit]The pharmacology of R6890 is described as a nociceptin receptor (NOP) agonist, although R6890 retains significant affinity at the mu opioid receptor.[6] R6890 has affinities (Ki values) of 4, 75, and 10 nM for the mu, delta, and the total opioid receptor population, respectively.[7]
See also
[edit]References
[edit]- ↑ Leysen JE, Gommeren W, Niemegeers CJ (February 1983). "[3H]Sufentanil, a superior ligand for mu-opiate receptors: binding properties and regional distribution in rat brain and spinal cord". European Journal of Pharmacology. 87 (2–3): 209–225. doi:10.1016/0014-2999(83)90331-x. PMID 6132825.
- ↑ Caldwell JP, Matasi JJ, Zhang H, Fawzi A, Tulshian DB (April 2007). "Synthesis and structure-activity relationships of N-substituted spiropiperidines as nociceptin receptor ligands". Bioorganic & Medicinal Chemistry Letters. 17 (8): 2281–2284. doi:10.1016/j.bmcl.2007.01.069. PMID 17289383.
- ↑ Caldwell JP, Matasi JJ, Fernandez X, McLeod RL, Zhang H, Fawzi A, et al. (February 2009). "Synthesis and structure-activity relationships of N-substituted spiropiperidines as nociceptin receptor ligands: part 2". Bioorganic & Medicinal Chemistry Letters. 19 (4): 1164–1167. doi:10.1016/j.bmcl.2008.12.092. PMID 19147350.
- ↑ Stahl KD, van Bever W, Janssen P, Simon EJ (December 1977). "Receptor affinity and pharmacological potency of a series of narcotic analgesic, anti-diarrheal and neuroleptic drugs". European Journal of Pharmacology. 46 (3): 199–205. doi:10.1016/0014-2999(77)90334-x. PMID 22440.
- ↑ Schedules of Controlled Substances: Temporary Placement of 5,6- Dichloro Brorphine, 5,6-Dichloro Desmethylchlorphine, N-Propionitrile Chlorphine, and Spirochlorphine in Schedule I of the Controlled Substances Act. Department of Justice, Drug Enforcement Administration. 21 CFR Part 1308. Docket No. DEA-1665. 1 July 2026
- ↑ Zaveri NT (1 May 2011). "The nociceptin/orphanin FQ receptor (NOP) as a target for drug abuse medications". Current Topics in Medicinal Chemistry. 11 (9): 1151–1156. doi:10.2174/156802611795371341. PMC 3899399. PMID 21050175.
- ↑ Galzi JL, Mejean A, Ilien B, Mollereau C, Meunier JC, Goeldner M, et al. (September 1990). "Photoactivatable opiate derivatives as irreversible probes of the mu-opioid receptor". Journal of Medicinal Chemistry. 33 (9): 2456–2464. doi:10.1021/jm00171a020. PMID 2167979.