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SML0058

Sigma-Aldrich

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
MDL number:
MFCD00882474
UNSPSC Code:
12352202
PubChem Substance ID:
329825124
NACRES:
NA.77

assay

≥98% (HPLC)

form

powder

storage condition

desiccated

color

white to beige

solubility

H2O: 15 mg/mL, clear

storage temp.

2-8°C

SMILES string

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

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+

InChI key

OKDOWCKDTWNRCB-GQCTYLIASA-N

Application

CGP 39551 may be used in cell signaling studies.

Biochem/physiol Actions

CGP 39551 is a competitive NMDA antagonist and anticonvulsant.
CGP 39551 is an orally active competitive NMDA antagonist and anticonvulsant.
CGP 39551 produces excitatory effects and causes psychotomimetic effects in humans.[1]

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_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
112M4625V

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B Monti et al.
The European journal of neuroscience, 12(9), 3117-3123 (2000-09-21)
Elimination of neurons produced in excess naturally occurs during brain development through programmed cell death. Among the many survival factors affecting this process, a role for neurotransmitters acting on specific receptors has been suggested. We have performed an in vivo
R D'Hooge et al.
Fundamental & clinical pharmacology, 13(1), 67-74 (1999-02-23)
The effects of CGP 37849 [DL-(E)-2-amino-4-methyl-5-phosphono-3-pentenoate] and its ethylester CGP 39551 on whole-cell currents evoked by the endogenous excitatory amino acids, L-glutamate and L-aspartate, were studied in cultured mouse spinal cord neurones. Although CGP 37849 was the more potent compound
W Löscher et al.
The Journal of pharmacology and experimental therapeutics, 256(2), 432-440 (1991-02-01)
The orally active competitive N-methyl-D-aspartate (NMDA) receptor antagonists CGP 37849 (DL-[E]-2-amino-4-methyl-5-phosphono-3-pentenoic acid) and its ethyl ester CGP 39551 were evaluated in amygdala-kindled rats, a model for complex partial and secondarily generalized seizures. Anticonvulsant and behavioral effects of these novel compounds
B Schilström et al.
Neuroscience, 125(4), 957-964 (2004-05-04)
In the present study, using single cell recordings in vivo and intracellular recordings in vitro from midbrain slices, the role of N-methyl-d-aspartate (NMDA) receptor signaling on firing activity in ventral tegmental area dopamine neurons elicited by nicotine was investigated in
Tamzin L Ripley et al.
Psychopharmacology, 163(2), 157-165 (2002-08-31)
It has previously been shown that drugs, such as benzodiazepines, that inhibit seizure activity during ethanol withdrawal, fail to alleviate the potentiated withdrawal seen following repeated episodes of withdrawal when administered during each withdrawal episode. Acute administration of the N-methyl-
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