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(2R,4R)-APDC

Product Name
(2R,4R)-APDC
CAS No.
169209-63-6
Chemical Name
(2R,4R)-APDC
Synonyms
4R)-APDC;LY-314,593;(2R,4R)-APDC;2R, 4R-APDC monohydrate;(2R,4R)APDC,(2R,4R) APDC;4-amino-2,4-pyrrolidinedicarboxylic acid;(2R,4R)-4-AMINOPYRROLIDINE-2,4-DICARBOXYLATE;(2R,4R)-4-AMINOPYRROLIDINE-2,4-DICARBOXYLIC ACID;2,4-Pyrrolidinedicarboxylic acid, 4-amino-, (2R,4R)-;2,4-Pyrrolidinedicarboxylicacid,4-amino-,(2R,4R)-(9CI)
CBNumber
CB5772407
Molecular Formula
C6H10N2O4
Formula Weight
174.15
MOL File
169209-63-6.mol
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(2R,4R)-APDC Property

storage temp. 
Desiccate at RT
solubility 
H2O: ≥2mg/mL
form 
powder
color 
white
Water Solubility 
Soluble to 100 mM in water
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Safety

Hazard Codes 
Xn
Risk Statements 
22-36/37/38
Safety Statements 
26
WGK Germany 
3
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Tocris
Product number
1208
Product name
(2R,4R)-APDC
Purity
≥98%(HPLC)
Packaging
10
Price
$255
Updated
2021/12/16
Tocris
Product number
1208
Product name
(2R,4R)-APDC
Purity
≥98%(HPLC)
Packaging
50
Price
$1071
Updated
2021/12/16
TRC
Product number
A726238
Product name
(2R,4R)-APDC
Packaging
1mg
Price
$65
Updated
2021/12/16
TRC
Product number
A726238
Product name
(2R,4R)-APDC
Packaging
2.5mg
Price
$130
Updated
2021/12/16
American Custom Chemicals Corporation
Product number
CCH0001246
Product name
(2R,4R)-APDC
Purity
95.00%
Packaging
1MG
Price
$202.65
Updated
2021/12/16
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(2R,4R)-APDC Chemical Properties,Usage,Production

Uses

(2R,4R)-APDC is a potent and selective group II metabotropic glutamate receptor agonist (1,2). It has been shown that (2R,4R)-APDC decrease cell proliferation in the dentate gyrus of adult rats (1).

Definition

ChEBI: (2R,4R)-4-aminopyrrolidine-2,4-dicarboxylic acid is a pyrrolidinedicarboxylic acid.

Biological Activity

A highly selective and relatively potent group II metabotropic glutamate receptor agonist. EC 50 values are 0.4, 0.4, > 100, > 100, > 300 and > 300 μ M for human mGlu 2 , mGlu 3 , mGlu 1 , mGlu 5 , mGlu 4 and mGlu 7 receptors respectively. Centrally active following systemic administration in vivo . Also available as part of the Group II mGlu Receptor Tocriset™ .

in vitro

2r,4r-apdc blocked forskolin-stimulated camp with none of the other activities of ls,3r-acpd. forskolin-stimulated camp formation in human mglur2 expressing cells with about three-fold greater potency than ls,3r-acpd were also inhibited by 2r,4r-apdc, which, unlike ls,3r-acpd, exhibited no appreciable activation of phosphoinostide hydrolysis in human mglur. thus, 2r,4r-apdc should be a useful pharmacological tool to explore the functions of mglurs coupled to inhibition of adenylate cyclase [1]. the effects of four isomers of apdc were investigated at glutamate receptors in vitro. (2r,4r)-apdc, an aza analog of the nonselective mglur agonist (1s,3r)-acpd possessed relatively high affinity for metabotropic glutamate receptors (mglurs) with no effects on radioligand binding to nmda, ampa, or kainate receptors up to 100 ím. none of the other apdc isomers exhibited significant mglur binding affinity, indicating that this interaction is highly stereospecific [2].

in vivo

both (1s,3r)-acpd and (2r,4r)-apdc were effectively attenuating forskolin-stimulated camp formation in the adult rat cerebral cortex; however, while (1s,3r)-acpd was also effectively stimulating basal tritiated inositol monophosphate production of the neonatal rat cerebral cortex, (2r,4r)-apdc was not effectively stimulating phosphoinositide hydrolysis in this tissue preparation. an augmentation of ampa-induced excitation was produced by microelectrophoretic application of either (1s,3r)-acpd or (2r,4r)-apdc to intact rat spinal neurons [2].

storage

Desiccate at RT

References

[1] schoepp dd, johnson bg, salhoff cr, valli mj, desai ma, burnett jp, mayne ng, monn ja. selective inhibition of forskolin-stimulated cyclic amp formation in rat hippocampus by a novel mglur agonist, 2r,4r-4-aminopyrrolidine-2,4- dicarboxylate. neuropharmacology. 1995 aug;34(8):843-50.
[2] monn ja, valli mj, johnson bg, salhoff cr, wright ra, howe t, bond a, lodge d, spangle la, paschal jw, campbell jb, griffey k, tizzano jp, schoepp dd. synthesis of the four isomers of 4-aminopyrrolidine-2,4-dicarboxylate: identification of a potent, highly selective, and systemically-active agonist for metabotropic glutamate receptors negatively coupled to adenylate cyclase. j med chem. 1996 jul 19; 39 (15):2990-3000.

(2R,4R)-APDC Preparation Products And Raw materials

Raw materials

Preparation Products

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(2R,4R)-APDC Suppliers

3B Pharmachem (Wuhan) International Co.,Ltd.
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TargetMol Chemicals Inc.
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Energy Chemical
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Beijing Jin Ming Biotechnology Co., Ltd.
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