Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C7H16NO5P |
Molecular Weight | 225.1794 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
N[C@H](CCCCCP(O)(O)=O)C(O)=O
InChI
InChIKey=MYDMWESTDPJANS-ZCFIWIBFSA-N
InChI=1S/C7H16NO5P/c8-6(7(9)10)4-2-1-3-5-14(11,12)13/h6H,1-5,8H2,(H,9,10)(H2,11,12,13)/t6-/m1/s1
Molecular Formula | C7H16NO5P |
Molecular Weight | 225.1794 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/6755315
Sources: https://www.ncbi.nlm.nih.gov/pubmed/6755315
(-)-AP-7 is an active isomer of 2-amino-7-phosphonoheptanoic acid, an NMDA receptor antagonist.
Originator
Sources: https://www.ncbi.nlm.nih.gov/pubmed/6111052
Curator's Comment: 1981
Approval Year
PubMed
Title | Date | PubMed |
---|---|---|
Phosphonate analogues of carboxylic acids as aminoacid antagonists on rat cortical neurones. | 1981 May 29 |
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Isomers of 2-amino-7-phosphonoheptanoic acid as antagonists of neuronal excitants. | 1982 Sep 20 |
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The effects of intrahippocampal ibotenic acid and their blockade by (-) 2-amino-7-phosphonoheptanoic acid: morphological and electroencephalographical analysis. | 1983 |
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N-methyl-D-aspartate receptor activation is required for the induction of both early and late phases of long-term potentiation in rat hippocampal slices. | 1989 Jan 2 |
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Evidence for the involvement of excitatory amino acid pathways in the development of precipitated withdrawal from acute and chronic morphine: an in vivo voltammetric study in the rat locus coeruleus. | 1993 Sep 24 |
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Behavioral effects of D-AP7 in rats subjected to experimental hypoxia. | 2003 May-Jun |
Patents
Sample Use Guides
rats: 25 ug i.c.v.; 2.5, 5.0 and 10 ug/site intrahippocampal
Route of Administration:
Other
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2564651
The action of the specific NMDA receptor antagonists (-)-2-amino-7-phosphonoheptanoic acid (D-APH) and 2-amino-5-phosphonovaleric acid (DL-APV) as well as of the inactive isomer L-APH was tested on orthodromic population excitatory postsynaptic potential (EPSP) and population spike (PS) responses recorded extracellularly from CA1 pyramidal cells. If the active D-isomer of APH (10 microM) or DL-APV (50 microM), but not if L-APH was present during tetanization, both EPSP and spike potentiation were markedly reduced or even blocked for the whole recording period (8 h after tetanization).
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 08:54:16 GMT 2023
by
admin
on
Sat Dec 16 08:54:16 GMT 2023
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Record UNII |
89FET0690I
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Record Status |
Validated (UNII)
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Record Version |
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1617430
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81338-23-0
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