L-AP4

L-AP4
Clinical data
Other names	L-2-Amino-4-phosphonobutyric acid
Identifiers
	IUPAC name (2S)-2-Amino-4-phosphonobutanoic acid;
CAS Number	23052-81-5;
PubChemCID	179394;
IUPHAR/BPS	1410;
ChemSpider	156157;
UNII	C8M58SS68H;
CompTox Dashboard(EPA)	DTXSID30945733;
ECHA InfoCard	100.164.384
Chemical and physical data
Formula	C4H10NO5P
Molar mass	183.100g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C(CP(=O)(O)O)[C@@H](C(=O)O)N;
	InChI InChI=1S/C4H10NO5P/c5-3(4(6)7)1-2-11(8,9)10/h3H,1-2,5H2,(H,6,7)(H2,8,9,10)/t3-/m0/s1; Key:DDOQBQRIEWHWBT-VKHMYHEASA-N;
	(what is this?)(verify)

L-AP4(L-2-amino-4-phosphonobutyric acid) is a drug used in scientific research, which acts as a group-selectiveagonistfor the group IIImetabotropic 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 their various functions.^[2]^[3]^[4]^[5]

References

^Thomsen C (August 1997). "The L-AP4 receptor".General Pharmacology.29(2): 151–8.doi:10.1016/S0306-3623(96)00417-X.PMID 9251893.
^Lopez S, Turle-Lorenzo N, Acher F, De Leonibus E, Mele A, Amalric M (June 2007)."Targeting group III metabotropic glutamate receptors produces complex behavioral effects in rodent models of Parkinson's disease".The Journal of Neuroscience.27(25): 6701–11.doi:10.1523/JNEUROSCI.0299-07.2007.PMC6672706.PMID 17581957.
^Macinnes N, Duty S (February 2008). "Group III metabotropic glutamate receptors act as hetero-receptors modulating evoked GABA release in the globus pallidus in vivo".European Journal of Pharmacology.580(1–2): 95–9.doi:10.1016/j.ejphar.2007.10.030.PMID 18035348.
^Zhang HM, Chen SR, Pan HL (January 2009)."Effects of activation of group III metabotropic glutamate receptors on spinal synaptic transmission in a rat model of neuropathic pain".Neuroscience.158(2): 875–84.doi:10.1016/j.neuroscience.2008.10.042.PMC2649787.PMID 19017536.
^Maciejak P, Szyndler J, Turzyńska D, Sobolewska A, Taracha E, Skórzewska A, et al. (July 2009). "The effects of group III mGluR ligands on pentylenetetrazol-induced kindling of seizures and hippocampal amino acids concentration".Brain Research.1282:20–7.doi:10.1016/j.brainres.2009.05.049.PMID 19481536.S2CID 20844494.

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[1] Thomsen C (August 1997). "The L-AP4 receptor".General Pharmacology.29(2): 151–8.doi:10.1016/S0306-3623(96)00417-X.PMID 9251893.

[2] Lopez S, Turle-Lorenzo N, Acher F, De Leonibus E, Mele A, Amalric M (June 2007)."Targeting group III metabotropic glutamate receptors produces complex behavioral effects in rodent models of Parkinson's disease".The Journal of Neuroscience.27(25): 6701–11.doi:10.1523/JNEUROSCI.0299-07.2007.PMC6672706.PMID 17581957.

[3] Macinnes N, Duty S (February 2008). "Group III metabotropic glutamate receptors act as hetero-receptors modulating evoked GABA release in the globus pallidus in vivo".European Journal of Pharmacology.580(1–2): 95–9.doi:10.1016/j.ejphar.2007.10.030.PMID 18035348.

[4] Zhang HM, Chen SR, Pan HL (January 2009)."Effects of activation of group III metabotropic glutamate receptors on spinal synaptic transmission in a rat model of neuropathic pain".Neuroscience.158(2): 875–84.doi:10.1016/j.neuroscience.2008.10.042.PMC2649787.PMID 19017536.

[5] Maciejak P, Szyndler J, Turzyńska D, Sobolewska A, Taracha E, Skórzewska A, et al. (July 2009). "The effects of group III mGluR ligands on pentylenetetrazol-induced kindling of seizures and hippocampal amino acids concentration".Brain Research.1282:20–7.doi:10.1016/j.brainres.2009.05.049.PMID 19481536.S2CID 20844494.

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