R6890

Spirochlorphine
Clinical data
Other namesSpirochlorphine
Identifiers
  • 8-[1-(4-chlorophenyl)ethyl]-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one
CAS Number
PubChem CID
ChemSpider
ChEMBL
Chemical and physical data
FormulaC21H24ClN3O
Molar mass369.89 g·mol−1
3D model (JSmol)
  • CC(C1=CC=C(C=C1)Cl)N2CCC3(CC2)C(=O)NCN3C4=CC=CC=C4
  • InChI=1S/C21H24ClN3O/c1-16(17-7-9-18(22)10-8-17)24-13-11-21(12-14-24)20(26)23-15-25(21)19-5-3-2-4-6-19/h2-10,16H,11-15H2,1H3,(H,23,26)
  • Key:KFEYPBZJPJJRFX-UHFFFAOYSA-N

R6890, sometimes known as spirochlorphine, is an orphine opioid analgesic and a member of the spiropiperidine family of agents. The first known mention of this compound was in 1977. 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.

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

The pharmacology of R6890 is described as a nociceptin receptor (NOP) agonist, although R6890 retains significant affinity at the mu opioid receptor in an animal model. R6890 has affinities (Ki values) of 4, 75, and 10 nM for the mu, delta, and the total opioid receptor population, respectively.

See also

References

  1. ↑ 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.
  2. ↑ 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.
  3. ↑ 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.
  4. ↑ 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.
  5. ↑ 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
  6. ↑ 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.
  7. ↑ 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.