ACPD

1-Amino-1,3-dicarboxycyclopentane (ACPD) is a chemical compound that binds to the metabotropic glutamate receptor (mGluR),[2] acting as a mGluR agonist. ACPD is a rigid analogue of the neurotransmitter glutamate and does not activate ionotropic glutamate receptors.[3] However, it has been reported to be an agonist of the glycine site of the NMDA receptor. ACPD can induce convulsions in neonatal rats.[4]

For other uses, see ACPD (disambiguation).
ACPD
Stereo, skeletal formula of ACPD ((1S,3S)-1-amino,-1,3-dicarboxylic acid)
Names
Preferred IUPAC name
1-Aminocyclopentane-1,3-dicarboxylic acid[1]
Identifiers
3D model (JSmol)
Abbreviations ACPD
ChEMBL
ChemSpider
MeSH 1-amino-1,3-dicarboxycyclopentane
RTECS number
  • GY4060000 (1S,3R)
  • InChI=1S/C7H11NO4/c8-7(6(11)12)2-1-4(3-7)5(9)10/h4H,1-3,8H2,(H,9,10)(H,11,12) ☒N
    Key: YFYNOWXBIBKGHB-UHFFFAOYSA-N ☒N
  • NC1(CCC(C1)C(O)=O)C(O)=O
Properties
C7H11NO4
Molar mass 173.168 g·mol−1
Appearance White crystals
20 g dm−3
Solubility in ethanol 240 mg dm−3
log P -0.709
Acidity (pKa) 2.112
Basicity (pKb) 11.885
Isoelectric point 2.84
Hazards
GHS labelling:
GHS07: Exclamation mark
Warning
H302, H312, H315, H319, H332, H335
P261, P280, P305+P351+P338
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

References
  1. "1-amino-1,3-dicarboxycyclopentane - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 25 March 2005. Identification and Related Records. Retrieved 15 October 2011.
  2. Schoepp DD, True RA (September 1992). "1S,3R-ACPD-sensitive (metabotropic) [3H]glutamate receptor binding in membranes". Neurosci. Lett. 145 (1): 100–4. doi:10.1016/0304-3940(92)90213-Q. PMID 1461560. S2CID 34921347.
  3. Manzoni O, Fagni L, Pin JP, Rassendren F, Poulat F, Sladeczek F, Bockaert J (July 1990). "(trans)-1-amino-cyclopentyl-1,3-dicarboxylate stimulates quisqualate phosphoinositide-coupled receptors but not ionotropic glutamate receptors in striatal neurons and Xenopus oocytes". Mol. Pharmacol. 38 (1): 1–6. PMID 2164627.
  4. McDonald JW, Fix AS, Tizzano JP, Schoepp DD (October 1993). "Seizures and brain injury in neonatal rats induced by 1S,3R-ACPD, a metabotropic glutamate receptor agonist". J. Neurosci. 13 (10): 4445–55. doi:10.1523/JNEUROSCI.13-10-04445.1993. PMC 6576384. PMID 8410197.


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