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L-AP4

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Chemical compound Pharmaceutical compound
L-AP4
Clinical data
Other namesL-2-Amino-4-phosphonobutyric acid
Identifiers
IUPAC name
  • (2S)-2-Amino-4-phosphonobutanoic acid
CAS Number
PubChem CID
IUPHAR/BPS
ChemSpider
UNII
CompTox Dashboard (EPA)
ECHA InfoCard100.164.384 Edit this at Wikidata
Chemical and physical data
FormulaC4H10NO5P
Molar mass183.100 g·mol
3D model (JSmol)
SMILES
  • C(CP(=O)(O)O)(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-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, 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.

References

  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.
Metabotropic glutamate receptor modulators
Group I
mGluR1Tooltip Metabotropic glutamate receptor 1
mGluR5Tooltip Metabotropic glutamate receptor 5
Group II
mGluR2Tooltip Metabotropic glutamate receptor 2
mGluR3Tooltip Metabotropic glutamate receptor 3
Group III
mGluR4Tooltip Metabotropic glutamate receptor 4
mGluR6Tooltip Metabotropic glutamate receptor 6
mGluR7Tooltip Metabotropic glutamate receptor 7
mGluR8Tooltip Metabotropic glutamate receptor 8
See also: Receptor/signaling modulators • Ionotropic glutamate receptor modulators • Glutamate metabolism/transport modulators
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