DL-2-Amino-5-phosphonovaleric acid (AP5)A potent NMDA antagonist

DL-2-Amino-5-phosphonovaleric acid (AP5) (CAS 76326-31-3)

DL-2-Amino-5-phosphonovaleric acid (AP5) | CAS 76326-31-3 is rated 5.0 out of 5 by 1.
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Synonym: APV; DL-APV
Application: A potent NMDA antagonist
CAS Number: 76326-31-3
Purity: ≥98%
Molecular Weight: 197.13
Molecular Formula: C5H12NO5P
* Refer to Certificate of Analysis for lot specific data (including water content).
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DL-2-Amino-5-phosphonovaleric acid (DL-AP5) is an N-methyl-D-aspartate (NMDA; sc-200458) receptor antagonist. Interference of this compound with NMDA receptors has shown to be the mechanism behind its potent and selective antagonistic characteristic towards synaptic and amino-acid induced excitation. Additionally, in brain synapsic studies DL-AP5 has been reported to reverse NMDA inhibition of glutamate release evoked by 4-aminopyridine (sc-202421).


References

1. Davies, J. and Watkins, J.C. 1982. Brain Res. 235: 378-386. PMID: 6145492
2. Sequeira, S.M., et al. 2001. Brain Res. Mol. Brain Res. 89: 111-118. PMID: 11311981
3. Vigh, J. and Witkovsky, P. 2004. Vis. Neurosci. 21: 1-11. PMID: 15137577

Physical State :
Solid
Solubility :
Soluble in water (5.6 mg/ml), 0.1 M NaOH (4 mg/ml), and 1M NH4(OH). Insoluble in organic solvents.
Storage :
Store at room temperature
Melting Point :
246-248° C
Boiling Point :
482.14° C at 760 mmHg (Predicted)
Density :
1.53 g/cm3 (Predicted)
Refractive Index :
n20D 1.54 (Predicted)
IC50 :
Glutamate NMDA receptor: IC50 = 290 nM (Rattus norvegicus)
Ki Data :
Glutamate NMDA receptor: Ki= 260 nM (Rattus norvegicus)
pK Values :
pKa: 2.47 (Predicted), pKb: 9.81 (Predicted)
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
WGK Germany :
3
PubChem CID :
1216
MDL Number :
MFCD00010515
Beilstein Registry :
2446389
SMILES :
C(CC(C(=O)O)N)CP(=O)(O)O

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Certificate of Analysis

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DL-2-Amino-5-phosphonovaleric acid (AP5)  Product Citations

See how others have used DL-2-Amino-5-phosphonovaleric acid (AP5). Click on the entry to view the PubMed entry .

Citations 1 to 3 of 3 total

PMID: # 29162813  Lalonde, J. et al. 2017. Nat Commun. 8: 1659.

PMID: # 27522962  O'Brien, M. et al. 2016. Neuroscience. 334: 236-244.

PMID: # 24704516  Wong, H. et al. 2014. Neuroscience. 269: 232-44.

Citations 1 to 3 of 3 total
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Rated 5 out of 5 by from Vigh et al Vigh et al. (PubMed ID 15137577) used DL-2-Amino-5-phosphonovaleric acid (AP5) to block the late component of excitatory postsynaptic potential (EPSP) by inhibiting NMDA. -SCBT Publication Review
Date published: 2015-07-10
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