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A182

Sigma-Aldrich

trans-(1S,3R)-ACPD

>97%, solid

Synonym(s):

trans-(1S,3R)-1-Amino-1,3-cyclopentanedicarboxylic acid

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About This Item

Empirical Formula (Hill Notation):
C7H11NO4
CAS Number:
111900-32-4
Molecular Weight:
173.17
MDL number:
MFCD00153760
UNSPSC Code:
12352200
PubChem Substance ID:
24890591

assay

>97%

form

solid

color

white

solubility

ethanol: 0.24 mg/mL
H2O: 20 mg/mL

SMILES string

N[C@]1(CC[C@H](C1)C(O)=O)C(O)=O

Gene Information

human ... GRM1(2911) , GRM2(2912) , GRM3(2913) , GRM4(2914) , GRM6(2916) , GRM7(2917) , GRM8(2918)
rat ... Gria1(50592) , Grik1(29559) , Grin2b(24410) , Grm1(24414) , Grm2(24415) , Grm4(24417) , Grm5(24418)

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Biochem/physiol Actions

Selective metabotropic glutamate receptor agonist; active enantiomer of trans-(±)-ACPD.

Other Notes

Note: under IUPAC nomenclature, this compound is designated cis.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

Certificates of Analysis (COA)

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J W McDonald et al.
European journal of pharmacology, 215(2-3), 353-354 (1992-05-14)
The role of metabotropic type excitatory amino acid receptors in brain injury was assessed using the selective metabotropic receptor agonist, (1S,3R)-1-aminocyclopentane-1,3-dicarboxylic acid (1S,3R-ACPD). Intrastriatal stereotaxic injection of 1S,3R-ACPD (250 nmol) in PND 7 rats produced little brain injury as assessed
D D Schoepp et al.
Neuroscience letters, 145(1), 100-104 (1992-09-28)
Metabotropic glutamate receptors are selectively activated by 1S,3R-1-aminocyclopentane-1,3-dicarboxylic acid (1S,3R-ACPD). [3H]Glutamate binding sites in rat brain membranes were characterized in the presence of (RS)-alpha-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid (AMPA), kainate, and N-methyl-D-aspartate (NMDA) to block binding to ionotropic glutamate receptors. 1S,3R-ACPD displaced a
Víctor M Blanco et al.
American journal of physiology. Heart and circulatory physiology, 294(6), H2855-H2863 (2008-05-06)
A growing number of studies support an important contribution of astrocytes to neurovascular coupling, i.e., the phenomenon by which variations in neuronal activity trigger localized changes in blood flow that serve to match the metabolic demands of neurons. However, since
G N Andrianov et al.
Hearing research, 204(1-2), 200-209 (2005-06-01)
Using immunocytochemistry and multiunit recording of afferent activity of the whole vestibular nerve, we investigated the role of metabotropic glutamate receptors (mGluR) in the afferent neurotransmission in the frog semicircular canals (SCC). Group I (mGluR1alpha) and group II (mGluR2/3) mGluR
R Cerne et al.
Neuroscience letters, 144(1-2), 180-184 (1992-09-14)
In freshly isolated spinal dorsal horn (DH) neurons (laminae I-IV) of the young rat the effects of 25-100 microM of (+/-)-trans-1-aminocyclopentane-1,3-dicarboxylic acid (trans-ACPD), 1S,3R-ACPD and 1R,3S-ACPD, a metabotropic glutamate receptor (mGluR) agonist, on inward currents induced by glutamate (Glu), alpha-amino-3-hydroxy-5-methyl-4-isoxazolepropionic
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