R6890 Explained
| Drug Name: | Spirochlorphine |
| Width: | 250px |
| Cas Number: | 3222-88-6 |
| Pubchem: | 14783734 |
| Chemspiderid: | 21257352 |
| Chembl: | 312281 |
| Synonyms: | Spirochlorphine |
| 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.[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. 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]
Notes and References
- Leysen JE, Gommeren W, Niemegeers CJ . [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 . February 1983 . 6132825 . 10.1016/0014-2999(83)90331-x .
- Caldwell JP, Matasi JJ, Zhang H, Fawzi A, Tulshian DB . Synthesis and structure-activity relationships of N-substituted spiropiperidines as nociceptin receptor ligands . Bioorganic & Medicinal Chemistry Letters . 17 . 8 . 2281–2284 . April 2007 . 17289383 . 10.1016/j.bmcl.2007.01.069 .
- Caldwell JP, Matasi JJ, Fernandez X, McLeod RL, Zhang H, Fawzi A, Tulshian DB . Synthesis and structure-activity relationships of N-substituted spiropiperidines as nociceptin receptor ligands: part 2 . Bioorganic & Medicinal Chemistry Letters . 19 . 4 . 1164–1167 . February 2009 . 19147350 . 10.1016/j.bmcl.2008.12.092 .
- Stahl KD, van Bever W, Janssen P, Simon EJ . Receptor affinity and pharmacological potency of a series of narcotic analgesic, anti-diarrheal and neuroleptic drugs . European Journal of Pharmacology . 46 . 3 . 199–205 . December 1977 . 22440 . 10.1016/0014-2999(77)90334-x .
- Zaveri NT . The nociceptin/orphanin FQ receptor (NOP) as a target for drug abuse medications . Current Topics in Medicinal Chemistry . 11 . 9 . 1151–1156 . 1 May 2011 . 21050175 . 10.2174/156802611795371341 . 3899399 .
- Galzi JL, Mejean A, Ilien B, Mollereau C, Meunier JC, Goeldner M, Hirth C . Photoactivatable opiate derivatives as irreversible probes of the mu-opioid receptor . Journal of Medicinal Chemistry . 33 . 9 . 2456–2464 . September 1990 . 2167979 . 10.1021/jm00171a020 .
