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LSP2-9166

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LSP2-9166

Identifiers

IUPAC name

(2S)-2-amino-4-[[[4-(carboxymethoxy)-3-(trifluoromethoxy)phenyl]-hydroxymethyl]-hydroxyphosphoryl]butanoic acid

PubChem CID

71042034

ChemSpider

98651888

Chemical and physical data

Formula

C₁₄H₁₇F₃NO₉P

Molar mass

431.257 g·mol⁻¹

3D model (JSmol)

Interactive image

SMILES

C1=CC(=C(C=C1C(O)P(=O)(CC[C@@H](C(=O)O)N)O)OC(F)(F)F)OCC(=O)O

InChI

InChI=1S/C14H17F3NO9P/c15-14(16,17)27-10-5-7(1-2-9(10)26-6-11(19)20)13(23)28(24,25)4-3-8(18)12(21)22/h1-2,5,8,13,23H,3-4,6,18H2,(H,19,20)(H,21,22)(H,24,25)/t8-,13?/m0/s1

Key:NTRJZUQSNSIKLO-OADYLZGLSA-N

LSP2-9166 is a drug which acts as a selective agonist for the group III metabotropic glutamate receptors, with a reasonably potent EC₅₀ of 70nM at mGluR₄ and 220nM at mGluR₇, and weaker activity of 1380nM at mGluR₆ and 4800nM at mGluR₈.^[1] It has anticonvulsant effects in animal studies,^[2]^[3] and reduces self-administration of various addictive drugs.^[4]^[5]^[6]

References[edit]

^ Acher FC, Cabayé A, Eshak F, Goupil-Lamy A, Pin JP (February 2022). "Metabotropic glutamate receptor orthosteric ligands and their binding sites". Neuropharmacology. 204: 108886. doi:10.1016/j.neuropharm.2021.108886. PMID 34813860.

^ Girard B, Tuduri P, Moreno MP, Sakkaki S, Barboux C, Bouschet T, et al. (September 2019). "The mGlu7 receptor provides protective effects against epileptogenesis and epileptic seizures". Neurobiology of Disease. 129: 13–28. doi:10.1016/j.nbd.2019.04.016. PMID 31051234.

^ Kovalenko AA, Zakharova MV, Schwarz AP, Dyomina AV, Zubareva OE, Zaitsev AV (March 2022). "Changes in Metabotropic Glutamate Receptor Gene Expression in Rat Brain in a Lithium-Pilocarpine Model of Temporal Lobe Epilepsy". International Journal of Molecular Sciences. 23 (5): 2752. doi:10.3390/ijms23052752. PMC 8910969. PMID 35269897.

^ Hajasova Z, Canestrelli C, Acher F, Noble F, Marie N (March 2018). "Role of mGlu7 receptor in morphine rewarding effects is uncovered by a novel orthosteric agonist". Neuropharmacology. 131: 424–430. doi:10.1016/j.neuropharm.2018.01.002. PMID 29307544. S2CID 3391450.

^ Lebourgeois S, Vilpoux C, Jeanblanc J, Acher F, Marie N, Noble F, Naassila M (May 2018). "Pharmacological activation of mGlu4 and mGlu7 receptors, by LSP2-9166, reduces ethanol consumption and relapse in rat". Neuropharmacology. 133: 163–170. doi:10.1016/j.neuropharm.2018.01.031. PMID 29378211. S2CID 3959313.