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Merck
CN

SML0058

CGP 39551

≥98% (HPLC)

Synonym(s):

CGP 39551, (E)-(±)-2-Amino-4-methyl-5-phosphono-3-pentenoic acid ethyl ester

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About This Item

Empirical Formula (Hill Notation):
C8H16NO5P
CAS Number:
127910-32-1
Molecular Weight:
237.19
NACRES:
NA.77
PubChem Substance ID:
329825124
UNSPSC Code:
12352202
MDL number:
MFCD00882474

Key Documents

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InChI

1S/C8H16NO5P/c1-3-14-8(10)7(9)4-6(2)5-15(11,12)13/h4,7H,3,5,9H2,1-2H3,(H2,11,12,13)/b6-4+

SMILES string

CCOC(=O)C(N)\C=C(/C)CP(O)(O)=O

InChI key

OKDOWCKDTWNRCB-GQCTYLIASA-N

assay

≥98% (HPLC)

form

powder

storage condition

desiccated

color

white to beige

solubility

H2O: 15 mg/mL, clear

storage temp.

2-8°C

Application

CGP 39551 may be used in cell signaling studies.

Biochem/physiol Actions

CGP 39551 produces excitatory effects and causes psychotomimetic effects in humans.
CGP 39551 is a competitive NMDA antagonist and anticonvulsant.
CGP 39551 is an orally active competitive NMDA antagonist and anticonvulsant.

Features and Benefits

This compound is featured on the Glutamate Receptors (Ion Channel Family) page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

pictograms

Skull and crossbones
GHS06

signalword

Danger

hcodes

H301

Hazard Classifications

Acute Tox. 3 Oral

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
112M4625V

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Barbara Monti et al.
The European journal of neuroscience, 16(8), 1490-1498 (2002-10-31)
During both in vivo and in vitro development, cerebellar granule cells depend on the activity of the NMDA glutamate receptor subtype for survival and full differentiation. With the present results, we demonstrate that CREB activation, downstream of the NMDA receptor
J J Kim et al.
Proceedings of the National Academy of Sciences of the United States of America, 93(10), 4750-4753 (1996-05-14)
Behavioral stress has detrimental effects on subsequent cognitive performance in many species, including humans. For example, humans exposed to stressful situations typically exhibit marked deficits in various learning and memory tasks. However, the underlying neural mechanisms by which stress exerts
Agnès Gruart et al.
The Journal of neuroscience : the official journal of the Society for Neuroscience, 26(4), 1077-1087 (2006-01-27)
One of the brain sites more directly related with learning and memory processes is the hippocampus. We recorded, in conscious mice, the activity-dependent changes taking place at the hippocampal CA3-CA1 synapse during the acquisition, extinction, recall, and reconditioning of an
W Zajaczkowski et al.
Neuropharmacology, 36(7), 961-971 (1997-07-01)
In general, N-methyl-D-aspartate (NMDA) receptor antagonists inhibit learning and long term potentiation (LTP). However, it has been suggested that direct tonic, i.e. non-temporal, activation of NMDA receptors, in contrast to learning, may lead to an increase in synaptic "noise" and
M M Marcus et al.
Neuropharmacology, 40(4), 482-490 (2001-03-16)
The effects of acute intravenous administration of the non-competitive NMDA receptor antagonists, phencyclidine (PCP), dizocilpine (MK-801; (+)-5-methyl-10,11-dihydroxy-5H-dibenzo(a,b)cyclohepten-5,10-imine), and the competitive NMDA receptor antagonist CGP 39551 (DL-(E)-2-amino-4-methyl-5-phosphono-3-pentanoic acid) on extracellular dopamine concentrations were analyzed in the shell and core subdivisions of
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