Compound

RB-64

Also called 22-thiocyanatosalvinorin a

Original Wikipedia articleen.wikipedia.org/wiki/RB-64 revision used (24 October 2026)

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Overview

RB-64, also known as 22-thiocyanatosalvinorin A, is a semi-synthetic derivative of salvinorin A. It is an irreversible agonist, with a reactive thiocyanate group that forms a bond to the κ-opioid receptor (KOR), resulting in very high potency. It is functionally selective, activating G proteins more potently than β-arrestin-2. RB-64 has a bias factor of up to 96 and is analgesic with fewer of the side-effects associated with unbiased KOR agonists. The analgesia is long-lasting. Compared with unbiased agonists, RB-64 evokes considerably less receptor internalization.[1][2][3] WP

Chemistry

Formula: C24H27NO8S PC
CAS number: 1174223-49-4 PC
Molar mass (g/mol): 489.5 PC
IUPAC name (computed by PubChem): 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 PC
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 PC
InChIKey: AZPUAKGNQXURGA-ZWLNRFIDSA-N PC
PubChem CID: 73347341

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Sources

Journal / agency Yan F, Bikbulatov RV, Mocanu V, Dicheva N, Parker CE, Wetsel WC, Mosier PD, Westkaemper RB, Allen JA, Zjawiony JK, Roth BL. Structure-based design, synthesis, and biochemical and pharmacological characterization of novel salvinorin A analogues as active state probes of the kappa-opioid receptor. Biochemistry. July 2009. doi:10.1021/bi900605n · PMID 19555087 · PMC2752672
Journal / agency White KL, Scopton AP, Rives ML, Bikbulatov RV, Polepally PR, Brown PJ, Kenakin T, Javitch JA, Zjawiony JK, Roth BL. Identification of novel functionally selective κ-opioid receptor scaffolds. Molecular Pharmacology. January 2014. doi:10.1124/mol.113.089649 · PMID 24113749 · PMC3868907
Journal / agency White KL, Robinson JE, Zhu H, DiBerto JF, Polepally PR, Zjawiony JK, Nichols DE, Malanga CJ, Roth BL. The G protein-biased κ-opioid receptor agonist RB-64 is analgesic with a unique spectrum of activities in vivo. The Journal of Pharmacology and Experimental Therapeutics. January 2015. doi:10.1124/jpet.114.216820 · PMID 25320048 · PMC4279099

Text and values on this page are quoted from Wikipedia (CC BY-SA 4.0), PubChem (public domain). Each value links to the exact revision it came from.