A155

trans-(±)-ACPD monohydrate

Name: <I>trans</I>-(±)-ACPD monohydrate
Brand: SIGMA

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

Key Documents

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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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This Item	P2371	A4978	SML0223
Sigma-Aldrich A155 trans-(±)-ACPD monohydrate	Sigma-Aldrich P2371 Pamidronate disodium salt hydrate	Sigma-Aldrich A4978 Alendronate sodium trihydrate	Sigma-Aldrich SML0223 Zoledronic acid monohydrate
form solid	form solid	form powder	form powder
assay ≥97% (NMR)	assay ≥95% (NMR)	assay ≥97% (NMR)	assay ≥98% (HPLC)
Quality Level 100	Quality Level 100	Quality Level 100	Quality Level 100
solubility H₂O: 1 mg/mL	solubility H₂O: 28 mg/mL	solubility water, double-distilled: 10 mg/mL	solubility H₂O: ≥2 mg/mL
color white	color white	color white	color white to beige
Gene Information human ... GRM1(2911), GRM2(2912), GRM3(2913), GRM4(2914), GRM5(2915), GRM6(2916), GRM7(2917), GRM8(2918)	Gene Information -	Gene Information human ... FDPS(2224)	Gene Information -

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

GHS07

Signal Word

Warning

Hazard Statements

H302 + H312 + H332

Precautionary Statements

P261 - P264 - P280 - P301 + P312 - P302 + P352 + P312 - P304 + P340 + P312

Hazard Classifications

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

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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In vitro and in vivo pharmacology of trans- and cis-(+-)-1-amino-1,3-cyclopentanedicarboxylic acid: dissociation of metabotropic and ionotropic excitatory amino acid receptor effects.

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

The glucocorticoid-Angptl4-ceramide axis induces insulin resistance through PP2A and PKCζ.

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

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)

Tone-dependent vascular responses to astrocyte-derived signals.

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

Autoradiographic imaging of phosphoinositide turnover in the brain.

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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