R6890

Last updated

Spirochlorphine
Spirochlorphine.svg
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
Formula C21H24ClN3O
Molar mass 369.89 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 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] It has been advertised online as a research chemical having a potency 2-5 times that of fentanyl.[ citation needed ] Other examples of agents from this class are Ro 64-6198 and Ro65-6570. Brorphine also has a similar structure.

A precursor chemical used in the synthesis of R6890 is 1-phenyl-1,3,8-triazaspiro(4,5)decan-4-one, which is used in the synthesis of other drugs including spirilene, fluspirilene, spiramide, spiperone, RP-23618, spioxatrine, and L008716.

Pharmacology

The pharmacology of R6890 is described as a nociceptin receptor (NOP) agonist, although R6890 retains significant activity at the mu opioid receptor. [5] R6890 has affinities (Ki values) of 4, 75, and 10 nM for the mu, delta, and the total opioid receptor population, respectively. [6]

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. ↑ 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.
  6. ↑ 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.
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