U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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-LURJTMIESA-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-/m0/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 inactive isomer of 2-amino-7-phosphonoheptanoic acid, an NMDA receptor antagonist.

Originator

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
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
Stereospecificity of N-MDA-induced functional deficits.
1990
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
Isomers of 2-amino-7-phosphonoheptanoic acid as antagonists of neuronal excitants.
1982-09-20

Sample Use Guides

(+)-AP-7 is inactive in rats: 25 ug i.c.v.; 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
DK0IVR1IZJ
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
(+)-2-AMINO-7-PHOSPHONOHEPTANOIC ACID
Preferred Name English
AP-7, (+)-
Common Name English
L-(+)-2-AMINO-7-PHOSPHONOHEPTANOIC ACID
Systematic Name English
HEPTANOIC ACID, 2-AMINO-7-PHOSPHONO-, (2S)-
Systematic Name English
Code System Code Type Description
PUBCHEM
6348564
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
EPA CompTox
DTXSID101000167
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
81338-24-1
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
FDA UNII
DK0IVR1IZJ
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