77-LH-28-1

77-LH-28-1
Identifiers
	IUPAC name 1-[3-(4-butylpiperidin-1-yl)propyl]-3,4-dihydroquinolin-2-one;
CAS Number	560085-11-2;
PubChem CID	10236758;
IUPHAR/BPS	3271;
ChemSpider	8412246;
UNII	9ZH28BM589;
CompTox Dashboard (EPA)	DTXSID90437063 ;
Chemical and physical data
Formula	C21H32N2O
Molar mass	328.500 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C2N(c1ccccc1CC2)CCCN3CCC(CC3)CCCC;
	InChI InChI=1S/C21H32N2O/c1-2-3-7-18-12-16-22(17-13-18)14-6-15-23-20-9-5-4-8-19(20)10-11-21(23)24/h4-5,8-9,18H,2-3,6-7,10-17H2,1H3; Key:PHMGZAICAOYEAF-UHFFFAOYSA-N;

77-LH-28-1 is a selective agonist of muscarinic acetylcholine receptor subtype 1 (M₁) discovered in 2008. It is an allosteric agonist, exhibiting over 100-fold specificity for M₁ over other muscarinic receptor subtypes. 77-LH-28-1 penetrates the brain by crossing the blood–brain barrier and is therefore a useful pharmacological tool with cognition enhancing effects.^[1] It has been used as a lead compound for discovery of other M1 agonists, and a crystal structure of the bound complex between 77-LH-28-1 and the M1 receptor has been published.^[2]

References

^ Langmead CJ, Austin NE, Branch CL, Brown JT, Buchanan KA, Davies CH, et al. (July 2008). "Characterization of a CNS penetrant, selective M1 muscarinic receptor agonist, 77-LH-28-1". British Journal of Pharmacology. 154 (5): 1104–1115. doi:10.1038/bjp.2008.152. PMC 2451039. PMID 18454168.
^ Brown AJ, Bradley SJ, Marshall FH, Brown GA, Bennett KA, Brown J, et al. (November 2021). "From structure to clinic: Design of a muscarinic M1 receptor agonist with potential to treatment of Alzheimer's disease". Cell. 184 (24): 5886–5901.e22. doi:10.1016/j.cell.2021.11.001. PMC 7616177. PMID 34822784.

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[1] Langmead CJ, Austin NE, Branch CL, Brown JT, Buchanan KA, Davies CH, et al. (July 2008). "Characterization of a CNS penetrant, selective M1 muscarinic receptor agonist, 77-LH-28-1". British Journal of Pharmacology. 154 (5): 1104–1115. doi:10.1038/bjp.2008.152. PMC 2451039. PMID 18454168.

[2] Brown AJ, Bradley SJ, Marshall FH, Brown GA, Bennett KA, Brown J, et al. (November 2021). "From structure to clinic: Design of a muscarinic M1 receptor agonist with potential to treatment of Alzheimer's disease". Cell. 184 (24): 5886–5901.e22. doi:10.1016/j.cell.2021.11.001. PMC 7616177. PMID 34822784.

[1]

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Identifiers

IUPAC name 1-[3-(4-butylpiperidin-1-yl)propyl]-3,4-dihydroquinolin-2-one
CAS Number	560085-11-2
PubChem CID	10236758
IUPHAR/BPS	3271
ChemSpider	8412246
UNII	9ZH28BM589
CompTox Dashboard (EPA)	DTXSID90437063
Chemical and physical data
Formula	C₂₁H₃₂N₂O
Molar mass	328.500 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES O=C2N(c1ccccc1CC2)CCCN3CCC(CC3)CCCC
InChI InChI=1S/C21H32N2O/c1-2-3-7-18-12-16-22(17-13-18)14-6-15-23-20-9-5-4-8-19(20)10-11-21(23)24/h4-5,8-9,18H,2-3,6-7,10-17H2,1H3 Key:PHMGZAICAOYEAF-UHFFFAOYSA-N