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Details

Stereochemistry RACEMIC
Molecular Formula C5H12NO5P
Molecular Weight 197.1262
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 2-AMINO-5-PHOSPHONOVALERATE

SMILES

NC(CCCP(O)(O)=O)C(O)=O

InChI

InChIKey=VOROEQBFPPIACJ-UHFFFAOYSA-N
InChI=1S/C5H12NO5P/c6-4(5(7)8)2-1-3-12(9,10)11/h4H,1-3,6H2,(H,7,8)(H2,9,10,11)

HIDE SMILES / InChI

Molecular Formula C5H12NO5P
Molecular Weight 197.1262
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
290.0 nM [IC50]
PubMed

PubMed

TitleDatePubMed
Defective hippocampal mossy fiber long-term potentiation in endothelial nitric oxide synthase knockout mice.
2001-09-01
Spreading depression in human neocortical slices.
2001-07-06
Effect of neonatal capsaicin treatment on neural activity in the medullary dorsal horn of neonatal rats evoked by electrical stimulation to the trigeminal afferents: an optical, electrophysiological, and quantitative study.
2001-07-06
Dopamine-independent locomotion following blockade of N-methyl-D-aspartate receptors in the ventral tegmental area.
2001-07
Increased spinal N-methyl-D-aspartate receptor function after 20 h of carrageenan-induced inflammation.
2001-07
Differential effects of NMDA antagonists microinjections into the nucleus reticularis pontis caudalis on seizures induced by pentylenetetrazol in the rat.
2001-07
N-Methyl-D-aspartate-induced c-Fos expression is enhanced in the forebrain structures related to emotion in Fyn-deficient mice.
2001-06-29
MAP2 phosphorylation and visual plasticity in Xenopus.
2001-06-29
The role of N-methyl-D-aspartate receptors in synaptic plasticity of rat visual cortex in vitro: effect of sensory experience.
2001-06-29
Gabaergic inhibition antagonizes adaptive adjustment of the owl's auditory space map during the initial phase of plasticity.
2001-06-15
Neurophysiological correlates of delayed visual differentiation tasks in monkeys: the effects of the site of intracortical blockade of NMDA receptors.
2001-06-05
The effects of an NDMA receptor antagonist on delayed visual differentiation in monkeys and rearrangements of neuron spike activity in the visual and prefrontal areas of the cortex.
2001-06-05
Unipolar brush cells form a glutamatergic projection system within the mouse cerebellar cortex.
2001-06-04
Amygdalar nmda receptors are critical for the expression of multiple conditioned fear responses.
2001-06-01
Injections of the NMDA receptor antagonist aminophosphonopentanoic acid into the lateral nucleus of the amygdala block the expression of fear-potentiated startle and freezing.
2001-06-01
NMDA-mediated activation of the medial amygdala initiates a downstream neuroendocrine memory responsible for pseudopregnancy in the female rat.
2001-06-01
Effects of adult neurogenesis on synaptic plasticity in the rat dentate gyrus.
2001-06
Dynamic modulation of excitation and inhibition during stimulation at gamma and beta frequencies in the CA1 hippocampal region.
2001-06
Local opiate withdrawal in locus coeruleus neurons in vitro.
2001-06
GABA(A)-dependent chloride influx modulates reversal potential of GABA(B)-mediated IPSPs in hippocampal pyramidal cells.
2001-06
Topical bicuculline to the rat spinal cord induces highly localized allodynia that is mediated by spinal prostaglandins.
2001-06
Early onset of glutamatergic and GABAergic synaptic activity in the visual layers of the rodent superior colliculus.
2001-06
Characterization of spontaneous excitatory synaptic currents in pyramidal cells of rat prelimbic cortex.
2001-05-18
Stress-induced increase in extracellular dopamine in striatum: role of glutamatergic action via N-methyl-D-aspartate receptors in substantia nigra.
2001-05-18
Melanin concentrating hormone depresses synaptic activity of glutamate and GABA neurons from rat lateral hypothalamus.
2001-05-15
Pharmacological aids to locomotor training after spinal injury in the cat.
2001-05-15
High-fidelity transmission acquired via a developmental decrease in NMDA receptor expression at an auditory synapse.
2001-05-15
A kainate receptor increases the efficacy of GABAergic synapses.
2001-05
Regulation of spontaneous inhibitory synaptic transmission by endogenous glutamate via non-NMDA receptors in cultured rat hippocampal neurons.
2001-05
Postsynaptic modulation of AMPA receptor-mediated synaptic responses and LTP by the type 3 ryanodine receptor.
2001-05
Kindling induces transient NMDA receptor-mediated facilitation of high-frequency input in the rat dentate gyrus.
2001-05
Post-episode depression of GABAergic transmission in spinal neurons of the chick embryo.
2001-05
Short-term plasticity at inhibitory synapses in rat striatum and its effects on striatal output.
2001-05
Enhanced temporal stability of cholinergic hippocampal gamma oscillations following respiratory alkalosis in vitro.
2001-05
Short-term synaptic depression in the neonatal mouse spinal cord: effects of calcium and temperature.
2001-05
Electrophysiological characterization of "giant" cells in stratum radiatum of the CA3 hippocampal region.
2001-05
Activation of group III mGluRs inhibits GABAergic and glutamatergic transmission in the substantia nigra pars reticulata.
2001-05
Activation of brainstem N-methyl-D-aspartate receptors is required for the analgesic actions of morphine given systemically.
2001-05
Ontogeny of ionotropic glutamate receptor expression in human fetal brain.
2001-04-30
NMDA and dopamine D2 receptors in the caudate-putamen are not involved in control of motor readiness in rats.
2001-04
An electrophysiological study of neural pathways for corticofugally inhibited neurons in the central nucleus of the inferior colliculus of the big brown bat, Eptesicus fuscus.
2001-04
Multiple-site optical recording reveals embryonic organization of synaptic networks in the chick spinal cord.
2001-04
Dopamine, but not glutamate, receptor blockade in the basolateral amygdala attenuates conditioned reward in a rat model of relapse to cocaine-seeking behavior.
2001-03
Stimulatory effect of endothelin-1 on neurons in the nucleus tractus solitarii is mediated by non-N-methyl-D-aspartate receptors.
2001-03
[The effect of metabotropic glutamate receptors on longitude of posttetanic reaction in spinal motoneurons of frog].
2001
Bidirectional modulation of basal forebrain N-methyl-D-aspartate receptor function differentially affects visual attention but not visual discrimination performance.
2001
Effect of lactate on the synaptic potential, energy metabolism, calcium homeostasis and extracellular glutamate concentration in the dentate gyrus of the hippocampus from guinea-pig.
2001
Modification of extracellular matrix by enzymatic removal of chondroitin sulfate and by lack of tenascin-R differentially affects several forms of synaptic plasticity in the hippocampus.
2001
PKC activation rescues LTP from NMDA receptor blockade.
2001
Differential mechanisms of Ca2+ responses in glial cells evoked by exogenous and endogenous glutamate in rat hippocampus.
2001
Patents

Patents

Substance Class Chemical
Created
by admin
on Mon Mar 31 21:29:48 GMT 2025
Edited
by admin
on Mon Mar 31 21:29:48 GMT 2025
Record UNII
39PJ29YY8Z
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
AP-5 (±)-
Preferred Name English
2-AMINO-5-PHOSPHONOVALERATE
Systematic Name English
AP 5 (AMINO ACID)
Common Name English
AP 5 (±)-
Common Name English
2-APV
Common Name English
NORVALINE, 5-PHOSPHONO- (±)-
Systematic Name English
(±)-AMINO-5-PHOSPHONOPENTANOIC ACID
Systematic Name English
DL-2-AMINO-5-PHOSPHONOVALERIC ACID
Common Name English
DL-2-AMINO-5-PHOSPHONOPENTANOIC ACID
Common Name English
5-PHOSPHONO-DL-NORVALINE
Systematic Name English
DL-AP-5
Code English
APV (±)-
Common Name English
DL-NORVALINE, 5-PHOSPHONO-
Systematic Name English
(±)-2-AMINO-5-PHOSPHONOVALERIC ACID
Systematic Name English
2-AMINO-5-PHOSPHONOVALERIC ACID
Systematic Name English
2-AMINO-5-PHOSPHONOPENTANOIC ACID
Systematic Name English
Classification Tree Code System Code
WIKIPEDIA NMDA receptor antagonist
Created by admin on Mon Mar 31 21:29:48 GMT 2025 , Edited by admin on Mon Mar 31 21:29:48 GMT 2025
Code System Code Type Description
PUBCHEM
1216
Created by admin on Mon Mar 31 21:29:48 GMT 2025 , Edited by admin on Mon Mar 31 21:29:48 GMT 2025
PRIMARY
CAS
76326-31-3
Created by admin on Mon Mar 31 21:29:48 GMT 2025 , Edited by admin on Mon Mar 31 21:29:48 GMT 2025
PRIMARY
WIKIPEDIA
2-Amino-5-phosphonovalerate
Created by admin on Mon Mar 31 21:29:48 GMT 2025 , Edited by admin on Mon Mar 31 21:29:48 GMT 2025
PRIMARY
MESH
D015763
Created by admin on Mon Mar 31 21:29:48 GMT 2025 , Edited by admin on Mon Mar 31 21:29:48 GMT 2025
PRIMARY
CHEBI
138644
Created by admin on Mon Mar 31 21:29:48 GMT 2025 , Edited by admin on Mon Mar 31 21:29:48 GMT 2025
PRIMARY
FDA UNII
39PJ29YY8Z
Created by admin on Mon Mar 31 21:29:48 GMT 2025 , Edited by admin on Mon Mar 31 21:29:48 GMT 2025
PRIMARY
EPA CompTox
DTXSID90893701
Created by admin on Mon Mar 31 21:29:48 GMT 2025 , Edited by admin on Mon Mar 31 21:29:48 GMT 2025
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
Binds to glutamate site
COMPETITIVE INHIBITOR
ACTIVE ENANTIOMER->RACEMATE
Related Record Type Details
ACTIVE MOIETY