L-AP4

L-AP4

Identifiers
IUPAC name (2S)-2-amino-4-phosphonobutanoic acid
CAS Number	23052-81-5
PubChem (CID)	179394
IUPHAR/BPS	1410
ChemSpider	156157
ECHA InfoCard	100.164.384
Chemical and physical data
Formula	C4H10NO5P
Molar mass	183.099 g/mol
3D model (Jmol)	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
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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 (mGluR_4/6/7/8). 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

1. Thomsen C (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 (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.
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.
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.
5. MacIejak P, Szyndler J, Turzyńska D, Sobolewska A, Taracha E, Skórzewska A, Lehner M, Bidziński A, Hamed A, Wisłowska-Stanek A, Płaźnik A (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.