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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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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

Quality Level

100

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

Signal Word

Warning

Hazard Statements

H302 + H312 + H332

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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)
Shilpa P Rao et al.
Glia, 55(16), 1680-1689 (2007-09-22)
Astrocytes are now recognized as dynamic signaling elements in the brain. Bidirectional communication between neurons and astrocytes involves integration of neuronal inputs by astrocytes and release of gliotransmitters that modulate neuronal excitability and synaptic transmission. The ovarian steroid hormone, 17beta-estradiol
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
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