Compound 9 (opioid antagonist)

Compound 9 (opioid antagonist)
Identifiers
	IUPAC name 6-[4-[(2-phenylethylamino)methyl]phenoxy]pyridine-3-carboxamide;
CAS Number	676494-79-4;
PubChem CID	44434058;
ChemSpider	23296584;
ChEMBL	ChEMBL238361;
Chemical and physical data
Formula	C21H21N3O2
Molar mass	347.418 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C1=CC=C(C=C1)CCNCC2=CC=C(C=C2)OC3=NC=C(C=C3)C(=O)N;
	InChI InChI=1S/C21H21N3O2/c22-21(25)18-8-11-20(24-15-18)26-19-9-6-17(7-10-19)14-23-13-12-16-4-2-1-3-5-16/h1-11,15,23H,12-14H2,(H2,22,25); Key:XPIWSPZHJZLUGI-UHFFFAOYSA-N;

Compound 9 is a highly potent non-selective opioid antagonist. It blocks all three of the μ, δ and κ opioid receptors with highest affinity at μ and weakest at κ. It has been researched as a potential treatment agent for opioid overdose associated with highly potent opioids such as carfentanil, which often fails to respond to conventional antidotes such as naloxone due to its high binding affinity at the mu opioid receptor.^[1]^[2]

References

^ Takeuchi K, Holloway WG, McKinzie JH, Suter TM, Statnick MA, Surface PL, et al. (October 2007). "Structure-activity relationship studies of carboxamido-biaryl ethers as opioid receptor antagonists (OpRAs). Part 1". Bioorganic & Medicinal Chemistry Letters. 17 (19): 5349–5352. doi:10.1016/j.bmcl.2007.08.008. PMID 17720493.
^ Martin J, Onyameh E, Luo D, Powell JW, Trivedi RR, Woloshin EJ, et al. (June 2025). "Searching for Synthetic Opioid Rescue Agents. 2: Identification of an Ultra-Potent Synthetic Opioid Rescue Agent". Journal of Medicinal Chemistry. 68 (12): 13057–13074. doi:10.1021/acs.jmedchem.5c01108. PMC 12238956. PMID 40499097.

[1] Takeuchi K, Holloway WG, McKinzie JH, Suter TM, Statnick MA, Surface PL, et al. (October 2007). "Structure-activity relationship studies of carboxamido-biaryl ethers as opioid receptor antagonists (OpRAs). Part 1". Bioorganic & Medicinal Chemistry Letters. 17 (19): 5349–5352. doi:10.1016/j.bmcl.2007.08.008. PMID 17720493.

[2] Martin J, Onyameh E, Luo D, Powell JW, Trivedi RR, Woloshin EJ, et al. (June 2025). "Searching for Synthetic Opioid Rescue Agents. 2: Identification of an Ultra-Potent Synthetic Opioid Rescue Agent". Journal of Medicinal Chemistry. 68 (12): 13057–13074. doi:10.1021/acs.jmedchem.5c01108. PMC 12238956. PMID 40499097.

[1]

[2]

See also

References