{{Short description|Opioid analgesic}} {{cs1 config|name-list-style=vanc|display-authors=6}} {{Infobox drug | drug_name = Spirochlorphine | image = Spirochlorphine.svg | image_class = skin-invert-image | width = 250px | caption =
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<!-- Identifiers --> | CAS_number = 3222-88-6 | CAS_supplemental = | PubChem = 14783734 | IUPHAR_ligand = | DrugBank = | ChemSpiderID = 21257352 | UNII = | KEGG = | ChEBI = | ChEMBL = 312281 | NIAID_ChemDB = | PDB_ligand = | synonyms = Spirochlorphine
<!--Chemical data--> | C=21 | H=24 | Cl=1 | N=3 | O=1 | IUPAC_name = 8-[1-(4-chlorophenyl)ethyl]-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one | StdInChI=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) | StdInChIKey = KFEYPBZJPJJRFX-UHFFFAOYSA-N | SMILES = CC(C1=CC=C(C=C1)Cl)N2CCC3(CC2)C(=O)NCN3C4=CC=CC=C4 }} '''R6890''', sometimes known as '''spirochlorphine''', is an opioid analgesic and a member of the spiropiperidine family of agents.<ref name="pmid6132825">{{cite journal | vauthors = Leysen JE, Gommeren W, Niemegeers CJ | title = [3H]Sufentanil, a superior ligand for mu-opiate receptors: binding properties and regional distribution in rat brain and spinal cord | journal = European Journal of Pharmacology | volume = 87 | issue = 2–3 | pages = 209–225 | date = February 1983 | pmid = 6132825 | doi = 10.1016/0014-2999(83)90331-x }}</ref><ref>{{cite journal | vauthors = Caldwell JP, Matasi JJ, Zhang H, Fawzi A, Tulshian DB | title = Synthesis and structure-activity relationships of N-substituted spiropiperidines as nociceptin receptor ligands | journal = Bioorganic & Medicinal Chemistry Letters | volume = 17 | issue = 8 | pages = 2281–2284 | date = April 2007 | pmid = 17289383 | doi = 10.1016/j.bmcl.2007.01.069 }}</ref><ref>{{cite journal | vauthors = Caldwell JP, Matasi JJ, Fernandez X, McLeod RL, Zhang H, Fawzi A, Tulshian DB | title = Synthesis and structure-activity relationships of N-substituted spiropiperidines as nociceptin receptor ligands: part 2 | journal = Bioorganic & Medicinal Chemistry Letters | volume = 19 | issue = 4 | pages = 1164–1167 | date = February 2009 | pmid = 19147350 | doi = 10.1016/j.bmcl.2008.12.092 }}</ref> The first known mention of this compound was in 1977.<ref name="pmid22440">{{cite journal | vauthors = Stahl KD, van Bever W, Janssen P, Simon EJ | title = Receptor affinity and pharmacological potency of a series of narcotic analgesic, anti-diarrheal and neuroleptic drugs | journal = European Journal of Pharmacology | volume = 46 | issue = 3 | pages = 199–205 | date = December 1977 | pmid = 22440 | doi = 10.1016/0014-2999(77)90334-x }}</ref> Other examples of agents from this class are Ro64-6198 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 (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.<ref>{{cite journal | vauthors = Zaveri NT | title = The nociceptin/orphanin FQ receptor (NOP) as a target for drug abuse medications | journal = Current Topics in Medicinal Chemistry | volume = 11 | issue = 9 | pages = 1151–1156 | date = 1 May 2011 | pmid = 21050175 | doi = 10.2174/156802611795371341 | pmc = 3899399 }}</ref> R6890 has affinities (K<sub>i</sub> values) of 4, 75, and 10 nM for the mu, delta, and the total opioid receptor population, respectively.<ref name="pmid2167979">{{cite journal | vauthors = Galzi JL, Mejean A, Ilien B, Mollereau C, Meunier JC, Goeldner M, Hirth C | title = Photoactivatable opiate derivatives as irreversible probes of the mu-opioid receptor | journal = Journal of Medicinal Chemistry | volume = 33 | issue = 9 | pages = 2456–2464 | date = September 1990 | pmid = 2167979 | doi = 10.1021/jm00171a020 }}</ref> ==See also== *Cychlorphine *List of orphine opioids
== References == {{Reflist}}
{{Analgesics}} {{Opioid receptor modulators}}
Category:Analgesics Category:Belgian inventions Category:Euphoriants Category:Mu-opioid receptor agonists Category:Piperidines Category:Synthetic opioids Category:4-Chlorophenyl compounds Category:Anilines Category:Spiro compounds Category:Imidazolidinones