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Merck
CN

A4910

Sigma-Aldrich

DL-2-Amino-3-phosphonopropionic acid

Synonym(s):

3-Phosphono-DL-alanine, AP-3

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About This Item

Empirical Formula (Hill Notation):
C3H8NO5P
CAS Number:
20263-06-3
Molecular Weight:
169.07
MDL number:
MFCD00014350
UNSPSC Code:
12352106
PubChem Substance ID:
24277949
NACRES:
NA.32

Key Documents

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form

powder

Quality Level

200

mp

227-229 °C (lit.)

SMILES string

NC(CP(O)(O)=O)C(O)=O

InChI

1S/C3H8NO5P/c4-2(3(5)6)1-10(7,8)9/h2H,1,4H2,(H,5,6)(H2,7,8,9)

InChI key

LBTABPSJONFLPO-UHFFFAOYSA-N

Gene Information

human ... GRM1(2911), GRM2(2912), GRM3(2913), GRM4(2914), GRM5(2915), GRM6(2916), GRM7(2917), GRM8(2918)

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Biochem/physiol Actions

Potent metabotropic glutamate receptor antagonist.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

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
0000207580
0000167081
0000167081
0000207580
0000144446

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K E Vogt et al.
Proceedings of the National Academy of Sciences of the United States of America, 96(3), 1118-1122 (1999-02-03)
Mossy fiber synapses form the major excitatory input into the autoassociative network of pyramidal cells in the CA3 area of the hippocampus. Here we demonstrate that at the mossy fiber synapses, glutamate and gamma-aminobutyric acid (GABA) act as autaptic and
Carlos Tejeda-Guzmán et al.
The Journal of experimental biology, 221(Pt 6) (2018-01-26)
Membrane transporters and sequestration mechanisms concentrate metal ions differentially into discrete subcellular microenvironments for use in protein cofactors, signalling, storage or excretion. Here we identify zinc storage granules as the insect's major zinc reservoir in principal Malpighian tubule epithelial cells
Akari Takai et al.
International journal of molecular sciences, 21(17) (2020-09-10)
Developmental and epileptic encephalopathies (DEEs) are the spectrum of severe epilepsies characterized by early-onset, refractory seizures occurring in the context of developmental regression or plateauing. Early infantile epileptic encephalopathy (EIEE) is one of the earliest forms of DEE, manifesting as
Tao Wang et al.
Molecular cancer research : MCR, 17(2), 398-408 (2018-09-30)
The αvβ3 integrin is involved in various physiologic and pathologic processes such as wound healing, angiogenesis, tumor growth, and metastasis. The impact of αvβ3 integrin on the radiosensitivity of prostate cancer cells and the molecular mechanism controlling cell survival in
T Banno et al.
The Journal of comparative neurology, 402(2), 252-263 (1998-12-09)
The intraventricular administrations of L-glutamate or trans-1-amino-1,3-cyclopentanedicarboxylic acid (t-ACPD), which is an agonist for the metabotropic glutamate receptor, induced conformational changes of the smooth endoplasmic reticulum (SER) to form lamellar bodies, consisting of stacks of flattened cisterns in Purkinje cell
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