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1-Amino-5-phosphonoindan-1-carboxylic acid

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This article is about the metabotropic glutamate receptor antagonist. For the cannabinoid drug, see SDB-001.
APICA
Clinical data
ATC code
  • none
Identifiers
  • 1-Amino-5-phosphonoindan-1-carboxylic acid
ChemSpider
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC10H12NO5P
Molar mass257.179 g/mol g·mol−1
3D model (JSmol)
  • O=P(O)(O)c(c2)ccc1c2CCC1(N)C(O)=O
  • InChI=1S/C10H12NO5P/c11-10(9(12)13)4-3-6-5-7(17(14,15)16)1-2-8(6)10/h1-2,5H,3-4,11H2,(H,12,13)(H2,14,15,16) checkY
  • Key:ZNQZXIHSJUDIKL-UHFFFAOYSA-N checkY
  (verify)

1-Amino-5-phosphonoindan-1-carboxylic acid (APICA) is a drug that is used in neuroscience research. It is a selective antagonist for the group II metabotropic glutamate receptors (mGluR2/3), and has been useful in the study of this receptor subfamily.[1][2][3][4][5]

References

  1. ^ Ma D, Tian H, Sun H, Kozikowski AP, Pshenichkin S, Wroblewski JT. Synthesis and biological activity of cyclic analogues of MPPG and MCPG as metabotropic glutamate receptor antagonists. Bioorganic & Medicinal Chemistry Letters. 1997 May 6;7(9):1195-1198. doi:10.1016/S0960-894X(97)00177-7
  2. ^ Ma D, Tian H, Zou G. Asymmetric Strecker-Type Reaction of alpha-Aryl Ketones. Synthesis of (S)-alphaM4CPG, (S)-MPPG, (S)-AIDA, and (S)-APICA, the Antagonists of Metabotropic Glutamate Receptors. Journal of Organic Chemistry. 1999 Jan 8;64(1):120-125. PMID 11674092
  3. ^ Xi ZX, Baker DA, Shen H, Carson DS, Kalivas PW. Group II metabotropic glutamate receptors modulate extracellular glutamate in the nucleus accumbens. Journal of Pharmacology and Experimental Therapeutics. 2002 Jan;300(1):162-71. doi:10.1124/jpet.300.1.162 PMID 11752112
  4. ^ Baker DA, Xi ZX, Shen H, Swanson CJ, Kalivas PW. The origin and neuronal function of in vivo nonsynaptic glutamate. Journal of Neuroscience. 2002 Oct 15;22(20):9134-41. PMID 12388621
  5. ^ Zhou F, Yao HH, Wu JY, Yang YJ, Ding JH, Zhang J, Hu G. Activation of Group II/III metabotropic glutamate receptors attenuates LPS-induced astroglial neurotoxicity via promoting glutamate uptake. Journal of Neuroscience Research. 2006 Aug 1;84(2):268-77. PMID 16752416
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