Skip to Content
MilliporeSigma
All Photos(5)

Key Documents

View All Documentation

A1910

Sigma-Aldrich

(±)-2-Amino-4-phosphonobutyric acid

solid

Synonym(s):

(±)-AP-4

Sign Into View Organizational & Contract Pricing

Select a Size

100 MG
$172.80
250 MG
$412.00
500 MG
$740.00
1 G
$1,200.00

$172.80

List Price$192.00Save 10%
Web-Only Promotion

Available to ship onApril 29, 2025Details

Request a Bulk Order
All Photos(5)

Select a Size

Change View
100 MG
$172.80
250 MG
$412.00
500 MG
$740.00
1 G
$1,200.00

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

$172.80

List Price$192.00Save 10%
Web-Only Promotion

Available to ship onApril 29, 2025Details

Request a Bulk Order

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)

Looking for similar products? Visit Product Comparison Guide

Related Categories

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.

Caution

Hygroscopic, store desiccated.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
0000373440
0000373440
0000253226
0000253225
0000234182

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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
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
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
View All Related Papers

Questions

Reviews

No rating value

Active Filters

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service