L(+)-2-Amino-4-phosphonobutanoic acid (L-AP4)A mGluR-4/6 receptor agonist

L(+)-2-Amino-4-phosphonobutanoic acid (L-AP4) (CAS 23052-81-5)

L(+)-2-Amino-4-phosphonobutanoic acid (L-AP4) | CAS 23052-81-5 is rated 5.0 out of 5 by 1.
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Synonym: L-AP4
Application: A mGluR-4/6 receptor agonist
CAS Number: 23052-81-5
Purity: ≥97%
Molecular Weight: 183.10
Molecular Formula: C4H10NO5P
* Refer to Certificate of Analysis for lot specific data (including water content).
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L(+)-2-Amino-4-phosphonobutanoic acid (L-AP4) is an amino-acid derivative and a mGluR-4 and mGluR-6 metabotropic glutamate receptor agonist. L-AP4 is also an agonist at the quisqualate-sensitized AP6 site in hippocampus. L-AP4 is a potent synaptic depressant. L(+)-2-Amino-4-phosphonobutanoic acid (L-AP4) is an activator of NMDA.


References

1. Koerner, J.F., et al. 1981. Brain Res. 216: 192-198. PMID: 6266585
2. Evans, R.H., et al. 1982. Br. J. Pharmacol. 75: 65-75. PMID: 7042024
3. Davies, J., et al. 1982. Brain Res. 235: 378-386. PMID: 6145492
4. Nakajima, Y., et al. 1993. J. Biol. Chem. 268: 11868-11873. PMID: 8389366
5. Kristensen, P., et al. 1993. Neurosci. Lett. 155: 159-162. PMID: 8104323
6. Saugstad, J.A., et al. 1994. Mol. Pharmacol. 45: 367-372. PMID: 8145723
7. Bushell, T.J., et al. 1995. Neuropharmacology. 34: 239-241. PMID: 7617150
8. Tones, M.A., et al. 1995. Neuroreport. 7: 117-120. PMID: 8742431
9. Ozawa, S., et al. 1998. Prog. Neurobiol. 54: 581-618. PMID: 9550192

Physical State :
Solid
Solubility :
Soluble in water (25 mg/ml), dilute aqueous base, and 1eq. NaOH (100 mM).
Storage :
Store at 4° C
Melting Point :
225-228° C
Boiling Point :
~491.7° C at 760 mmHg (Predicted)
Density :
~1.6 g/cm3 (Predicted)
Refractive Index :
n20D 1.55 (Predicted)
Optical Activity :
α20/D +24°, c = 1 in 6N HCl
IC50 :
Displace [3H]APB: IC50 = 1.5 µM (rat)
Ki Data :
Metabotropic glutamate receptor 8: Ki= 61 nM (human); Metabotropic glutamate receptor 4: Ki= 0.16 nM (human); Metabotropic glutamate receptor 6: Ki= 0.9 µM (human); Metabotropic glutamate receptor 8: Ki= 1.9 µM (human)
pK Values :
pKa: 2.19 (Predicted), pKb: 9.75 (Predicted)
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
WGK Germany :
3
PubChem CID :
179394
MDL Number :
MFCD00083244
SMILES :
C(CP(=O)(O)O)[C@@H](C(=O)O)N

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Certificate of Analysis

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Rated 5 out of 5 by from Takemoto Takemoto, Y. (PubMed 25450419) reported that microinjections of L-Cysteine and the mGluR-4/6 receptor agonist L-AP4 in the rat caudal ventrolateral medulla decreases arterial blood pressure. -SCBT Publication Review
Date published: 2015-01-02
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