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A1910

Sigma-Aldrich

(±)-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

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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General description

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

Application

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

Biochem/physiol Actions

NMDA glutamate receptor antagonist.

Caution

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

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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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
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
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
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
Satoshi Okado et al.
Investigative ophthalmology & visual science, 58(12), 5518-5525 (2017-10-28)
We determined the effects of a remodeled inner retina on the flicker electroretinograms (ERGs) in a rabbit eye at an advanced stage of inherited retinal degeneration. Six wild-type (WT) and four rhodopsin P347L transgenic (Tg) rabbits were studied at 18
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