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 ;
PubChem CID	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	183.100 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 ;
	(what is this?) (verify)

Last updated December 27, 2025

L-AP4 (L-2-amino-4-phosphonobutyric acid) 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 (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. PMC 6672706 . 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. PMC 2649787 . 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. PMC 6672706 . 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. PMC 2649787 . 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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