ACPD

{{other uses}}

{{Chembox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 477235244

| ImageFile = 1-amino-1,3-dicarboxycyclopentane.png

| ImageFile_Ref = {{chemboximage|correct|??}}

| ImageName = Stereo, skeletal formula of ACPD ((1S,3S)-1-amino,-1,3-dicarboxylic acid)

| PIN = 1-Aminocyclopentane-1,3-dicarboxylic acid{{Cite web|title = 1-amino-1,3-dicarboxycyclopentane - Compound Summary|url = https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=1310|work = PubChem Compound|publisher = National Center for Biotechnology Information|access-date = 15 October 2011|location = USA|date = 25 March 2005|at = Identification and Related Records}}

| Section1 = {{Chembox Identifiers

| Abbreviations = ACPD

| CASNo_Ref = {{cascite|changed|??}}

| CASNo = 39026-63-6

| CASNo1_Ref = {{cascite|correct|??}}

| CASNo1 = 56827-69-1

| CASNo1_Comment = (1R,3S)

| CASNo2_Ref = {{cascite|correct|??}}

| CASNo2 = 111900-32-4

| CASNo2_Comment = (1S,3R)

| PubChem = 1310

| PubChem1 = 44381972

| PubChem1_Comment = (1S)

| PubChem2 = 231345

| PubChem2_Comment = (1R,3R)

| PubChem3 = 73537

| PubChem3_Comment = (1R,3S)

| PubChem4 = 104766

| PubChem4_Comment = (1S,3R)

| PubChem5 = 6604704

| PubChem5_Comment = (1S,3S)

| ChemSpiderID = 1270

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID1 = 201559

| ChemSpiderID1_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID1_Comment = (1R,3R)

| ChemSpiderID2 = 66220

| ChemSpiderID2_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID2_Comment = (1R,3S)

| ChemSpiderID3 = 94574

| ChemSpiderID3_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID3_Comment = (1S,3R)

| ChemSpiderID4 = 5036967

| ChemSpiderID4_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID4_Comment = (1S,3S)

| MeSHName = 1-amino-1,3-dicarboxycyclopentane

| ChEMBL = 168278

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| RTECS = GY4060000 (1S,3R)

| SMILES = NC1(CCC(C1)C(O)=O)C(O)=O

| StdInChI = 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)

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = YFYNOWXBIBKGHB-UHFFFAOYSA-N

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

}}

| Section2 = {{Chembox Properties

| C = 7 | H = 11 | N = 1 | O = 4

| Appearance = White crystals

| Solubility = 20 g dm⁻³

| Solvent = ethanol

| SolubleOther = 240 mg dm⁻³

| LogP = −0.709

| pKa = 2.112

| pKb = 11.885

| IsoelectricPt = 2.84

}}

| Section3 = {{Chembox Hazards

| GHSPictograms = {{GHS exclamation mark}}

| GHSSignalWord = Warning

| HPhrases = {{H-phrases|302|312|315|319|332|335}}

| PPhrases = {{P-phrases|261|280|305+351+338}}

}}

}}

1-Amino-1,3-dicarboxycyclopentane (ACPD) is a chemical compound that binds to the metabotropic glutamate receptor (mGluR),{{cite journal |vauthors =Schoepp DD, True RA |title=1S,3R-ACPD-sensitive (metabotropic) [³H]glutamate receptor binding in membranes |journal=Neurosci. Lett. |volume=145 |issue=1 |pages=100–4 |date=September 1992 |pmid=1461560 |doi= 10.1016/0304-3940(92)90213-Q|s2cid=34921347 }} acting as a mGluR agonist. ACPD is a rigid analogue of the neurotransmitter glutamate and does not activate ionotropic glutamate receptors.{{cite journal |vauthors =Manzoni O, Fagni L, Pin JP, Rassendren F, Poulat F, Sladeczek F, Bockaert J |title=(trans)-1-amino-cyclopentyl-1,3-dicarboxylate stimulates quisqualate phosphoinositide-coupled receptors but not ionotropic glutamate receptors in striatal neurons and Xenopus oocytes |journal=Mol. Pharmacol. |volume=38 |issue=1 |pages=1–6 |date=July 1990 |pmid=2164627 |url=http://molpharm.aspetjournals.org/cgi/pmidlookup?view=long&pmid=2164627}} However, it has been reported to be an agonist of the glycine site of the NMDA receptor.{{Citation needed|date=August 2017}} ACPD can induce convulsions in neonatal rats.{{cite journal |vauthors =McDonald JW, Fix AS, Tizzano JP, Schoepp DD |title=Seizures and brain injury in neonatal rats induced by 1S,3R-ACPD, a metabotropic glutamate receptor agonist |journal=J. Neurosci. |volume=13 |issue=10 |pages=4445–55 |date=October 1993 |pmid=8410197 |pmc=6576384 |doi= 10.1523/JNEUROSCI.13-10-04445.1993}}