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A1910

(±)-2-Amino-4-phosphonobutyric acid

solid

Synonym(s):

(±)-AP-4

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About This Item

Empirical Formula (Hill Notation):
C4H10NO5P
CAS Number:
20263-07-4
Molecular Weight:
183.10
MDL number:
MFCD00013999
UNSPSC Code:
12352106
PubChem Substance ID:
57653830
NACRES:
NA.32

Key Documents

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form

solid

color

white

SMILES string

NC(CCP(O)(O)=O)C(O)=O

InChI

1S/C4H10NO5P/c5-3(4(6)7)1-2-11(8,9)10/h3H,1-2,5H2,(H,6,7)(H2,8,9,10)

InChI key

DDOQBQRIEWHWBT-UHFFFAOYSA-N

Gene Information

human ... GRIN1(2902), GRIN2A(2903), GRIN2B(2904), GRIN2C(2905), GRIN2D(2906), GRINA(2907)
rat ... Grin2b(24410)

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This Item
A7929165304AB15097
(±)-2-Amino-4-phosphonobutyric acid solid

Sigma-Aldrich

A1910

(±)-2-Amino-4-phosphonobutyric acid

L-(+)-2-Amino-4-phosphonobutyric acid optical purity optical purity: ≥95% (HPLC, Marfey′s reagent)

Sigma-Aldrich

A7929

L-(+)-2-Amino-4-phosphonobutyric acid

D-(–)-2-Amino-5-phosphonopentanoic Acid Active enantiomer of DL-2-amino-5-phosphonopentanoic acid (AP5) that is a commonly used as a competitive NMDA receptor antagonist.

Sigma-Aldrich

165304

D-(–)-2-Amino-5-phosphonopentanoic Acid

Anti-mGluR4 Antibody from rabbit

Sigma-Aldrich

AB15097

Anti-mGluR4 Antibody

form

solid

form

powder

form

solid

form

-

color

white

color

-

color

white

color

-

Gene Information

human ... GRIN1(2902), GRIN2A(2903), GRIN2B(2904), GRIN2C(2905), GRIN2D(2906), GRINA(2907)
rat ... Grin2b(24410)

Gene Information

human ... GRM1(2911), GRM2(2912), GRM3(2913), GRM4(2914), GRM6(2916), GRM7(2917), GRM8(2918)
rat ... Grm1(24414), Grm2(24415), Grm4(24417), Grm5(24418), Grm6(24419), Grm7(81672)

Gene Information

-

Gene Information

mouse ... Grm4(268934)

General description

(±)-2-Amino-4-phosphonobutyric acid or DL-AP4 is a group III nonselective metabotropic glutamate receptor (mGluR) agonist.[1] L-2-amino-4-phosphonobutyric acid (L-Ap4) displays close to 500-fold selectivity for group III mGluRs.[2]

Application

(±)-2-Amino-4-phosphonobutyric acid may be used as a glutamic acid receptor blocker in perfusion solution in the eye tissue electroretinography studies.[3]

Biochem/physiol Actions

NMDA glutamate receptor antagonist.

Disclaimer

Hygroscopic, store desiccated.

Storage Class Code

11 - 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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Certificates of Analysis (COA)

Lot/Batch Number
0000502523
0000502530
0000502530
0000502523
0000488338

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A Contractor et al.
Proceedings of the National Academy of Sciences of the United States of America, 95(15), 8969-8974 (1998-07-22)
The actions of glutamate in the central nervous system are mediated through interaction with fast activating ionotropic receptors and G protein-coupled metabotropic glutamate receptors (mGluRs). Studies of these receptors have relied on the availability of agonists and antagonists selective for
Alex S McKeown et al.
The Journal of physiology, 594(7), 1841-1854 (2015-12-23)
We propose that the end product of chromophore bleaching in rod photoreceptors, all-trans retinol, is part of a feedback loop that increases the sensitivity of the phototransduction cascade in rods. A previously described light-induced hypersensitivity in rods, termed adaptive potentiation
H-M Zhang et al.
Neuroscience, 158(2), 875-884 (2008-11-20)
Chronic neuropathic pain remains an unmet clinical problem because it is often resistant to conventional analgesics. Metabotropic glutamate receptors (mGluRs) are involved in nociceptive processing at the spinal level, but their functions in neuropathic pain are not fully known. In
Haruhisa Okawa et al.
Nature communications, 10(1), 2167-2167 (2019-05-17)
Ribbon synapses transmit information in sensory systems, but their development is not well understood. To test the hypothesis that ribbon assembly stabilizes nascent synapses, we performed simultaneous time-lapse imaging of fluorescently-tagged ribbons in retinal cone bipolar cells (BCs) and postsynaptic
Jared D Chrispell et al.
Investigative ophthalmology & visual science, 59(12), 5116-5124 (2018-10-30)
To define the functional roles of Grk1 and Grk7 in zebrafish cones in vivo. Genome editing was used to generate grk7a and grk1b knockout zebrafish. Electroretinogram (ERG) analyses of the isolated cone mass receptor potential and the b-wave were performed
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