Misplaced Pages

Spirochlorphine

Clinical data
Other names	Spirochlorphine
Identifiers
IUPAC name 8--1-phenyl-1,3,8-triazaspirodecan-4-one
CAS Number	3222-88-6
PubChem CID	14783734
ChemSpider	21257352
ChEMBL	ChEMBL312281
Chemical and physical data
Formula	C21H24ClN3O
Molar mass	369.89 g·mol
3D model (JSmol)	Interactive image
SMILES CC(C1=CC=C(C=C1)Cl)N2CCC3(CC2)C(=O)NCN3C4=CC=CC=C4
InChI 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. The first known mention of this compound was in 1977. It has been advertised online as a research chemical having a potency 2-5 times that of fentanyl. 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. R6890 has affinities (K_i values) of 4, 75, and 10 nM for the mu, delta, and the total opioid receptor population, respectively.

References

1. Leysen JE, Gommeren W, Niemegeers CJ (February 1983). "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.

• Analgesics
• Belgian inventions
• Euphoriants
• Mu-opioid receptor agonists
• Piperidines
• Synthetic opioids
• 4-Chlorophenyl compounds
• Anilines
• Spiro compounds
• Imidazolidinones