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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

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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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)
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
Harry C Winter et al.
Neurochemical research, 33(2), 223-231 (2007-10-18)
Noncyclic fluorine-substituted and cyclic analogs of glutamic acid were tested for their ability to inhibit glutamate uptake in isolated bovine presynaptic vesicles, in order to assess the specific structural requirements of the glutamate translocation system in the vesicle membrane. Cyclic
Matthew E Larkum et al.
Journal of neurophysiology, 99(2), 683-694 (2007-11-30)
The six-layered mammalian neocortex evolved from the three-layered paleocortex, which is retained in present-day reptiles such as the turtle. Thus the turtle offers an opportunity to examine which cellular and circuit properties are fundamental to cortical function. We characterized the
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