L-AP4

L-AP4
Identifiers
	IUPAC name (2S)-2-amino-4-phosphonobutanoic acid;
CAS Number	23052-81-5;
PubChem CID	179394;
CompTox Dashboard (EPA)	DTXSID30945733 ;
ECHA InfoCard	100.164.384
Chemical and physical data
Formula	C4H10NO5P
Molar mass	183.099 g/mol g·mol−1
3D model (JSmol)	Interactive image;
	SMILES OC(=O)C(N)CCP(O)(O)=O;

L-AP4 is a drug used in scientific research, which acts as a group-selective agonist for the group III metabotropic glutamate receptors (mGluR₄_/₆_/₇_/₈). It was the first ligand found to act as an agonist selective for this group of mGlu receptors,^[1] but does not show selectivity between the different mGluR Group III subtypes. It is widely used in the study of this receptor family and its various functions.^[2]^[3]^[4]^[5]

References

^ Thomsen C. The L-AP4 receptor. General Pharmacology. 1997 Aug;29(2):151-8. PMID 9251893
^ Lopez S, Turle-Lorenzo N, Acher F, De Leonibus E, Mele A, Amalric M. Targeting group III metabotropic glutamate receptors produces complex behavioral effects in rodent models of Parkinson's disease. Journal of Neuroscience. 2007 Jun 20;27(25):6701-11. PMID 17581957
^ Macinnes N, Duty S. Group III metabotropic glutamate receptors act as hetero-receptors modulating evoked GABA release in the globus pallidus in vivo. European Journal of Pharmacology. 2008 Feb 2;580(1-2):95-9. PMID 18035348
^ Zhang HM, Chen SR, Pan HL. Effects of activation of group III metabotropic glutamate receptors on spinal synaptic transmission in a rat model of neuropathic pain. Neuroscience. 2009 Jan 23;158(2):875-84. PMID 19017536
^ Maciejak P, Szyndler J, Turzyńska D, Sobolewska A, Taracha E, Skórzewska A, Lehner M, Bidziński A, Hamed A, Wisłowska-Stanek A, Płaźnik A. The effects of group III mGluR ligands on pentylenetetrazol-induced kindling of seizures and hippocampal amino acids concentration. Brain Research. 2009 Jul 28;1282:20-7. PMID 19481536

[1] Thomsen C. The L-AP4 receptor. General Pharmacology. 1997 Aug;29(2):151-8. PMID 9251893

[2] Lopez S, Turle-Lorenzo N, Acher F, De Leonibus E, Mele A, Amalric M. Targeting group III metabotropic glutamate receptors produces complex behavioral effects in rodent models of Parkinson's disease. Journal of Neuroscience. 2007 Jun 20;27(25):6701-11. PMID 17581957

[3] Macinnes N, Duty S. Group III metabotropic glutamate receptors act as hetero-receptors modulating evoked GABA release in the globus pallidus in vivo. European Journal of Pharmacology. 2008 Feb 2;580(1-2):95-9. PMID 18035348

[4] Zhang HM, Chen SR, Pan HL. Effects of activation of group III metabotropic glutamate receptors on spinal synaptic transmission in a rat model of neuropathic pain. Neuroscience. 2009 Jan 23;158(2):875-84. PMID 19017536

[5] Maciejak P, Szyndler J, Turzyńska D, Sobolewska A, Taracha E, Skórzewska A, Lehner M, Bidziński A, Hamed A, Wisłowska-Stanek A, Płaźnik A. The effects of group III mGluR ligands on pentylenetetrazol-induced kindling of seizures and hippocampal amino acids concentration. Brain Research. 2009 Jul 28;1282:20-7. PMID 19481536

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