RB-64

RB-64

Systematic (IUPAC) name
Methyl (2S,4aR,6aR,7R,9S,10aS,10bR)-2-(furan-3-yl)-6a,10b-dimethyl-4,10-dioxo-9-(2-thiocyanatoacetyl)oxy-2,4a,5,6,7,8,9,10a-octahydro-1H-benzo[f]isochromene-7-carboxylate
Legal status
Legal status	Legal/Uncontrolled
Identifiers
ATC code	none
PubChem	CID 73347341
ChemSpider	30812525 Y
ChEMBL	CHEMBL2381583 Y
Chemical data
Formula	C24H27NO8S
Molar mass	489.54 g/mol
3D model (Jmol)	Interactive image
SMILES C[C@@]12CC[C@H]3C(=O)O[C@@H](C[C@@]3([C@H]1C(=O)[C@H](C[C@H]2C(=O)OC)OC(=O)CSC#N)C)C4=COC=C4
InChI InChI=1S/C24H27NO8S/c1-23-6-4-14-22(29)33-17(13-5-7-31-10-13)9-24(14,2)20(23)19(27)16(8-15(23)21(28)30-3)32-18(26)11-34-12-25/h5,7,10,14-17,20H,4,6,8-9,11H2,1-3H3/t14-,15-,16-,17-,20-,23-,24-/m0/s1 Y[PubChem] Key:AZPUAKGNQXURGA-ZWLNRFIDSA-N Y[PubChem]

RB-64 or 22-thiocyanatosalvinorin A is a semi-synthetic salvonorin derivative and a κ-opioid receptor (KOR) agonist which is used in scientific research. Its most remarkable property is its biased activity in signal transduction in favour of G protein versus β-arrestin-2, a phenomenon which is called functional selectivity or biased agonism. RB-64 has a bias factor of 96 and is analgesic with fewer of the prototypical side-effects associated with unbiased KOR agonists. The analgesia-like effect is long-lasting. Compared with unbiased agonists RB-64 evokes considerably less receptor internalisation.

See also

• Herkinorin
• Salvinorin B methoxymethyl ether
• Salvinorin A
• Nalfurafine

Further reading

• Yan F, Bikbulatov RV, Mocanu V, et al. (July 2009). "Structure-Based Design, Synthesis, and Biochemical and Pharmacological Characterization of Novel Salvinorin A Analogues as Active State Probes of the κ-Opioid Receptor". Biochemistry. 48 (29): 6898–908. doi:10.1021/bi900605n. PMC 2752672. PMID 19555087. 
• White KL, Scopton AP, Rives ML, et al. (January 2014). "Identification of Novel Functionally Selective κ-Opioid Receptor Scaffolds". Molecular Pharmacology. 85 (1): 83–90. doi:10.1124/mol.113.089649. PMC 3868907. PMID 24113749.