DL-2-Amino-3-phosphonopropionic acid

3-Phosphono-DL-alanine, AP-3
Empirical Formula (Hill Notation):
Número de CAS:
Peso molecular:
Número MDL:
ID de la sustancia en PubChem:


227-229 °C (lit.)

SMILES string




InChI key


Gene Information

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

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100 mg in poly bottle

Acciones bioquímicas o fisiológicas

Potent metabotropic glutamate receptor antagonist.

Características y beneficios

This compound is also offered as part of Sigma′s Library of Pharmacologically Active Compounds (LOPAC®1280), a biologically annotated collection of high-quality, ready-to-screen compounds. Click here to learn more.

Otras notas

Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. A4910.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Información legal

LOPAC is a registered trademark of Sigma-Aldrich Co. LLC


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Palabra de señalización


Frases de peligro

Órganos de actuación

Respiratory system

Equipo de protección personal

dust mask type N95 (US), Eyeshields, Gloves


NONH for all modes of transport

WGK Alemania


Punto de inflamabilidad F

Not applicable

Punto de inflamabilidad C

Not applicable

G Pellegri et al.
The European journal of neuroscience, 10(1), 272-280 (1998-09-30)
In view of the neurotrophic effect of vasoactive intestinal peptide (VIP), the regulation of brain-derived neurotrophic factor (BDNF) expression by VIP and the related peptide pituitary adenylate cyclase-activating polypeptide (PACAP) was analysed by Northern blot in primary cultures of cortical...
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...
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...
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...
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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