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A155

Sigma-Aldrich

trans-(±)-ACPD monohydrate

solid, ≥97% (NMR)

Synonym(s):

trans-(±)-1-Amino-1,3-cyclopentanedicarboxylic acid monohydrate

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5 MG
$172.00
100 MG
$1,990.00

$172.00

Available to ship onApril 01, 2025Details

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5 MG
$172.00
100 MG
$1,990.00

About This Item

Empirical Formula (Hill Notation):
C7H11NO4 · H2O
CAS Number:
67684-64-4
Molecular Weight:
191.18
MDL number:
MFCD11046039
UNSPSC Code:
12352200
PubChem Substance ID:
24277952
NACRES:
NA.32

$172.00

Available to ship onApril 01, 2025Details

assay

≥97% (NMR)

form

solid

color

white

solubility

H2O: 1 mg/mL

SMILES string

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

InChI

1S/C7H11NO4.H2O/c8-7(6(11)12)2-1-4(3-7)5(9)10;/h4H,1-3,8H2,(H,9,10)(H,11,12);1H2/t4-,7+;/m1./s1

InChI key

AZRMVYVZWAKHMR-RERZVJIGSA-N

Gene Information

human ... GRM1(2911) , GRM2(2912) , GRM3(2913) , GRM4(2914) , GRM5(2915) , GRM6(2916) , GRM7(2917) , GRM8(2918)

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Biochem/physiol Actions

Excitatory amino acid receptor agonist; selective for the metabotropic glutamate receptor subtype.

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

Storage Class

13 - Non Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
047K46053
047K46052
047K46051
047K4605

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Tzu-Chieh Chen et al.
Science signaling, 10(489) (2017-07-27)
Chronic glucocorticoid exposure is associated with the development of insulin resistance. We showed that glucocorticoid-induced insulin resistance was attenuated upon ablation of Angptl4, a glucocorticoid target gene encoding the secreted protein angiopoietin-like 4, which mediates glucocorticoid-induced lipolysis in white adipose
D D Schoepp et al.
Journal of neurochemistry, 56(5), 1789-1796 (1991-05-01)
This study explored further the function of the metabotropic excitatory amino acid receptor in the rat brain. The trans and cis isomers of (+-)-1-amino-1,3-cyclopentane-dicarboxylic acid (ACPD) were characterized for relative affinities at ionotropic and metabotropic excitatory amino acid receptors in
Trans-ACPD, a selective agonist of the phosphoinositide-coupled excitatory amino acid receptor.
E Palmer et al.
European journal of pharmacology, 166(3), 585-587 (1989-08-03)
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
P M Hwang et al.
Science (New York, N.Y.), 249(4970), 802-804 (1990-08-17)
With [3H]cytidine as a precursor, phosphoinositide turnover can be localized in brain slices by selective autoradiography of the product [3H]cytidine diphosphate diacylglycerol, which is membrane-bound. In the cerebellum, glutamatergic stimulation elicits an increase of phosphoinositide turnover only in Purkinje cells
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