L-AP4

L-AP4
Identifiers
	IUPAC name (2S)-2-amino-4-phosphonobutanoic acid;
CAS Number	23052-81-5 ;
PubChem CID	179394;
IUPHAR/BPS	1412;
ChemSpider	156157;
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 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;
	(verify)

L-2-amino-4-phosphonobutyric acid (or 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 their various functions.^[2]^[3]^[4]^[5]

References

^ Thomsen, C (1997). "The L-AP4 receptor". General pharmacology. 29 (2): 151–8. doi:10.1016/S0306-3623(96)00417-X. PMID 9251893. {{cite journal}}: Cite has empty unknown parameter: |author-name-separator= (help); Unknown parameter |author-separator= ignored (help)
^ Lopez, S; Turle-Lorenzo, N; Acher, F; De Leonibus, E; Mele, A; Amalric, M (2007). "Targeting group III metabotropic glutamate receptors produces complex behavioral effects in rodent models of Parkinson's disease". Journal of Neuroscience. 27 (25): 6701–11. doi:10.1523/JNEUROSCI.0299-07.2007. PMID 17581957. {{cite journal}}: Cite has empty unknown parameter: |author-name-separator= (help); Unknown parameter |author-separator= ignored (help)
^ MacInnes, N; Duty, S (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. {{cite journal}}: Cite has empty unknown parameter: |author-name-separator= (help); Unknown parameter |author-separator= ignored (help)
^ Zhang, HM; Chen, SR; Pan, HL (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. PMC 2649787. PMID 19017536. {{cite journal}}: Cite has empty unknown parameter: |author-name-separator= (help); Unknown parameter |author-separator= ignored (help)
^ MacIejak, P; Szyndler, J; Turzyńska, D; Sobolewska, A; Taracha, E; Skórzewska, A; Lehner, M; Bidziński, A; Hamed, A; Wisłowska-Stanek, Aleksandra; Płaźnik, Adam (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. {{cite journal}}: Cite has empty unknown parameter: |author-name-separator= (help); Unknown parameter |author-separator= ignored (help)

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[1] Thomsen, C (1997). "The L-AP4 receptor". General pharmacology. 29 (2): 151–8. doi:10.1016/S0306-3623(96)00417-X. PMID 9251893. {{cite journal}}: Cite has empty unknown parameter: |author-name-separator= (help); Unknown parameter |author-separator= ignored (help)

[2] Lopez, S; Turle-Lorenzo, N; Acher, F; De Leonibus, E; Mele, A; Amalric, M (2007). "Targeting group III metabotropic glutamate receptors produces complex behavioral effects in rodent models of Parkinson's disease". Journal of Neuroscience. 27 (25): 6701–11. doi:10.1523/JNEUROSCI.0299-07.2007. PMID 17581957. {{cite journal}}: Cite has empty unknown parameter: |author-name-separator= (help); Unknown parameter |author-separator= ignored (help)

[3] MacInnes, N; Duty, S (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. {{cite journal}}: Cite has empty unknown parameter: |author-name-separator= (help); Unknown parameter |author-separator= ignored (help)

[4] Zhang, HM; Chen, SR; Pan, HL (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. PMC 2649787. PMID 19017536. {{cite journal}}: Cite has empty unknown parameter: |author-name-separator= (help); Unknown parameter |author-separator= ignored (help)

[5] MacIejak, P; Szyndler, J; Turzyńska, D; Sobolewska, A; Taracha, E; Skórzewska, A; Lehner, M; Bidziński, A; Hamed, A; Wisłowska-Stanek, Aleksandra; Płaźnik, Adam (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. {{cite journal}}: Cite has empty unknown parameter: |author-name-separator= (help); Unknown parameter |author-separator= ignored (help)

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