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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
Behavioral effects of D-AP7 in rats subjected to experimental hypoxia.
2003-01-23
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.
1993-09-24
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.
1989-01-02
The relative potencies of (-)-2-amino-5-phosphonovalerate and (-)-2-amino-7-phosphonoheptanoate as antagonists of N-methylaspartate and quinolinic acids and repetitive spikes in rat hippocampal slices.
1986-08-27
The effects of intrahippocampal ibotenic acid and their blockade by (-) 2-amino-7-phosphonoheptanoic acid: morphological and electroencephalographical analysis.
1983
Isomers of 2-amino-7-phosphonoheptanoic acid as antagonists of neuronal excitants.
1982-09-20
Phosphonate analogues of carboxylic acids as aminoacid antagonists on rat cortical neurones.
1981-05-29
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 Mon Mar 31 22:22:41 GMT 2025
Edited
by admin
on Mon Mar 31 22:22:41 GMT 2025
Record UNII
89FET0690I
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
(R)-AP7
Preferred Name English
AP-7, (-)-
Common Name English
D-(-)-2-AMINO-7-PHOSPHONOHEPTANOATE
Systematic Name 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 Mon Mar 31 22:22:41 GMT 2025 , Edited by admin on Mon Mar 31 22:22:41 GMT 2025
PRIMARY
PUBCHEM
1617430
Created by admin on Mon Mar 31 22:22:41 GMT 2025 , Edited by admin on Mon Mar 31 22:22:41 GMT 2025
PRIMARY
CAS
81338-23-0
Created by admin on Mon Mar 31 22:22:41 GMT 2025 , Edited by admin on Mon Mar 31 22:22:41 GMT 2025
PRIMARY