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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
Structure of AP-7, (-)-

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

HIDE SMILES / InChI

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

(-)-AP-7 is an active isomer of 2-amino-7-phosphonoheptanoic acid, an NMDA receptor antagonist.

Originator

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Phosphonate analogues of carboxylic acids as aminoacid antagonists on rat cortical neurones.
1981 May 29
Isomers of 2-amino-7-phosphonoheptanoic acid as antagonists of neuronal excitants.
1982 Sep 20
The effects of intrahippocampal ibotenic acid and their blockade by (-) 2-amino-7-phosphonoheptanoic acid: morphological and electroencephalographical analysis.
1983
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
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
Behavioral effects of D-AP7 in rats subjected to experimental hypoxia.
2003 May-Jun
Patents

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
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 Sat Dec 16 08:54:16 GMT 2023
Edited
by admin
on Sat Dec 16 08:54:16 GMT 2023
Record UNII
89FET0690I
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
AP-7, (-)-
Common Name English
D-(-)-2-AMINO-7-PHOSPHONOHEPTANOATE
Systematic Name English
(R)-AP7
Code English
HEPTANOIC ACID, 2-AMINO-7-PHOSPHONO-, (2R)-
Systematic Name English
D-AP 7
Code English
Code System Code Type Description
FDA UNII
89FET0690I
Created by admin on Sat Dec 16 08:54:16 GMT 2023 , Edited by admin on Sat Dec 16 08:54:16 GMT 2023
PRIMARY
PUBCHEM
1617430
Created by admin on Sat Dec 16 08:54:16 GMT 2023 , Edited by admin on Sat Dec 16 08:54:16 GMT 2023
PRIMARY
CAS
81338-23-0
Created by admin on Sat Dec 16 08:54:16 GMT 2023 , Edited by admin on Sat Dec 16 08:54:16 GMT 2023
PRIMARY