R6890

Spirochlorphine
Clinical data
Other names	Spirochlorphine
Identifiers
	IUPAC name 8-[1-(4-chlorophenyl)ethyl]-1-phenyl-1,3,8-triazaspiro[4.5]decan-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−1
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 marketed 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 some 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.

The precursor chemical is called 1-phenyl-1,3,8-triazaspiro(4,5)decan-4-one [1021-25-6]. This intermediate has a plethora of known uses. Named drugs also made from this compound include the following list of examples: spirilene, fluspirilene, spiramide, spiperone, RP-23618, spioxatrine & 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 (K_i values) of 4, 75, and 10 nM for the mu, delta, and the total opioid receptor population.^[6]

References

^ 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.
^ 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.

[pmid6132825-1] 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.

[pmid22440-4] 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.

[pmid2167979-6] 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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