A5352
L-(+)-2-Amino-6-phosphonohexanoic acid
≥98% (HPLC), solid
Synonym(s):
L-AP6
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About This Item
Empirical Formula (Hill Notation):
C6H14NO5P
CAS Number:
Molecular Weight:
211.15
NACRES:
NA.77
PubChem Substance ID:
UNSPSC Code:
12352200
MDL number:
Assay:
≥98% (HPLC)
Form:
solid
InChI key
QIOXWRQXHFVNLV-YFKPBYRVSA-N
SMILES string
N[C@@H](CCCCP(O)(O)=O)C(O)=O
InChI
1S/C6H14NO5P/c7-5(6(8)9)3-1-2-4-13(10,11)12/h5H,1-4,7H2,(H,8,9)(H2,10,11,12)/t5-/m0/s1
assay
≥98% (HPLC)
form
solid
color
white
Biochem/physiol Actions
L-(+)-2-Amino-6-phosphonohexanoic acid (L-AP6) is an excitatory glutamate analogue that is able to depolarize L-quisqualic acid (QUIS)-sensitized CA1 rat hippocampal neurons.
signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Gloves
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M K Schulte et al.
Brain research, 649(1-2), 203-207 (1994-06-27)
Brief exposure of rat hippocampal slices to quisqualic acid (QUIS) sensitizes neurons to depolarization by the alpha-amino-omega-phosphonate excitatory amino acid (EAA) analogues AP4, AP5 and AP6. These phosphonates interact with a novel QUIS-sensitized site. Whereas L-AP4 and D-AP5 cross-react with
L A Chase et al.
Neuroscience, 106(2), 287-301 (2001-09-22)
A brief exposure of hippocampal slices to L-quisqualic acid sensitizes CA1 pyramidal neurons 30-250-fold to depolarization by two classes of excitatory amino acid analogues: (1) those whose depolarizing effects are rapidly terminated following washout, e.g. L-2-amino-4-phosphonobutanoic acid (L-AP4) and L-2-amino-6-phosphonohexanoic
L A Chase et al.
Toxicology and applied pharmacology, 219(1), 1-9 (2007-01-20)
A brief exposure of hippocampal slices to L-quisqualic acid (QUIS) sensitizes CA1 pyramidal neurons 30- to 250-fold to depolarization by certain excitatory amino acids analogues, e.g., L-2-amino-6-phosphonohexanoic acid (L-AP6), and by the endogenous compound, L-cystine. This phenomenon has been termed
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