SER-601

SER-601
Clinical data
Routes of; administration	Oral
Identifiers
	IUPAC name N-(Adamant-1-yl)-1-pentyl-4-oxo-6-isopropyl-1,4-dihydroquinoline-3-carboxamide;
CAS Number	1048038-90-9 ;
PubChem CID	25034551;
ChemSpider	24606023 ;
UNII	S723GJY405;
ChEMBL	ChEMBL502276 ;
CompTox Dashboard (EPA)	DTXSID80648525 ;
Chemical and physical data
Formula	C28H38N2O2
Molar mass	434.624 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC(C)c5ccc(c1c5)n(CCCCC)cc(c1=O)C(=O)NC4(C2)CC(CC2C3)CC3C4;
	InChI InChI=1S/C28H38N2O2/c1-4-5-6-9-30-17-24(26(31)23-13-22(18(2)3)7-8-25(23)30)27(32)29-28-14-19-10-20(15-28)12-21(11-19)16-28/h7-8,13,17-21H,4-6,9-12,14-16H2,1-3H3,(H,29,32) ; Key:KUMKLUDNETVLDS-UHFFFAOYSA-N ;
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SER-601 (COR-167) is a drug which acts as a potent and selective cannabinoid CB₂ receptor agonist, based on a quinolone-3-carboxylic acid core structure, with 190 times selectivity for CB₂ over the related CB₁ receptor. It has analgesic effects in animal studies, as well as neuroprotective effects,^[1] but without a "cannabis high" due to its low affinity for CB₁.^[2] A number of related compounds are known, almost all of which have high selectivity for CB₂.^[3]

References

^ Contartese A, Valoti M, Corelli F, Pasquini S, Mugnaini C, Pessina F, et al. (December 2012). "A novel CB2 agonist, COR167, potently protects rat brain cortical slices against OGD and reperfusion injury". Pharmacological Research. 66 (6): 555–563. doi:10.1016/j.phrs.2012.08.003. PMID 23036353.
^ Pasquini S, Botta L, Semeraro T, Mugnaini C, Ligresti A, Palazzo E, et al. (August 2008). "Investigations on the 4-quinolone-3-carboxylic acid motif. 2. Synthesis and structure-activity relationship of potent and selective cannabinoid-2 receptor agonists endowed with analgesic activity in vivo". Journal of Medicinal Chemistry. 51 (16): 5075–5084. doi:10.1021/jm800552f. PMID 18680276.
^ Pasquini S, Ligresti A, Mugnaini C, Semeraro T, Cicione L, De Rosa M, et al. (August 2010). "Investigations on the 4-quinolone-3-carboxylic acid motif. 3. Synthesis, structure-affinity relationships, and pharmacological characterization of 6-substituted 4-quinolone-3-carboxamides as highly selective cannabinoid-2 receptor ligands". Journal of Medicinal Chemistry. 53 (16): 5915–5928. doi:10.1021/jm100123x. PMID 20718492.

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[1] Contartese A, Valoti M, Corelli F, Pasquini S, Mugnaini C, Pessina F, et al. (December 2012). "A novel CB2 agonist, COR167, potently protects rat brain cortical slices against OGD and reperfusion injury". Pharmacological Research. 66 (6): 555–563. doi:10.1016/j.phrs.2012.08.003. PMID 23036353.

[pmid18680276-2] Pasquini S, Botta L, Semeraro T, Mugnaini C, Ligresti A, Palazzo E, et al. (August 2008). "Investigations on the 4-quinolone-3-carboxylic acid motif. 2. Synthesis and structure-activity relationship of potent and selective cannabinoid-2 receptor agonists endowed with analgesic activity in vivo". Journal of Medicinal Chemistry. 51 (16): 5075–5084. doi:10.1021/jm800552f. PMID 18680276.

[pmid20718492-3] Pasquini S, Ligresti A, Mugnaini C, Semeraro T, Cicione L, De Rosa M, et al. (August 2010). "Investigations on the 4-quinolone-3-carboxylic acid motif. 3. Synthesis, structure-affinity relationships, and pharmacological characterization of 6-substituted 4-quinolone-3-carboxamides as highly selective cannabinoid-2 receptor ligands". Journal of Medicinal Chemistry. 53 (16): 5915–5928. doi:10.1021/jm100123x. PMID 20718492.

[1]

[2]

[3]

Clinical data

Routes of administration	Oral
Identifiers
IUPAC name N-(Adamant-1-yl)-1-pentyl-4-oxo-6-isopropyl-1,4-dihydroquinoline-3-carboxamide
CAS Number	1048038-90-9^Y
PubChem CID	25034551
ChemSpider	24606023^Y
UNII	S723GJY405
ChEMBL	ChEMBL502276^Y
CompTox Dashboard (EPA)	DTXSID80648525
Chemical and physical data
Formula	C₂₈H₃₈N₂O₂
Molar mass	434.624 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CC(C)c5ccc(c1c5)n(CCCCC)cc(c1=O)C(=O)NC4(C2)CC(CC2C3)CC3C4
InChI InChI=1S/C28H38N2O2/c1-4-5-6-9-30-17-24(26(31)23-13-22(18(2)3)7-8-25(23)30)27(32)29-28-14-19-10-20(15-28)12-21(11-19)16-28/h7-8,13,17-21H,4-6,9-12,14-16H2,1-3H3,(H,29,32)^Y Key:KUMKLUDNETVLDS-UHFFFAOYSA-N^Y
^NY (what is this?) (verify)

SER-601

See also

References