(E)-(+/-)-2-AMINO-4-METHYL-5-PHOSPHONO-3-PENTENOIC ACID ETHYL ESTER


CAS No. : 127910-32-1

(E)-(+/-)-2-AMINO-4-METHYL-5-PHOSPHONO-3-PENTENOIC ACID ETHYL ESTER,127910-32-1
Product Details
For research use only. Not Intended for Therapeutic Use!
Cat No:M113287
Synonyms:(R,E)-(4-amino-5-ethoxy-2-methyl-5-oxopent-2-en-1-yl)phosphonic acid
Molecular Formula:C8H16NO5P
Molecular Weight:237.192
Target:NMDA Receptor
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Appearance:Solid powder
Purity: > 98%
Cat No:M113287
Cas No:127910-32-1
Product-Name:(E)-(+/-)-2-AMINO-4-METHYL-5-PHOSPHONO-3-PENTENOIC ACID ETHYL ESTER
IUPAC Name:[(E)-4-amino-5-ethoxy-2-methyl-5-oxopent-2-enyl]phosphonic acid
InChI: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+
InChIKey:OKDOWCKDTWNRCB-GQCTYLIASA-N
SMILES:CCOC(=O)C(C=C(C)CP(=O)(O)O)N
Cgp 39551 is a potent and selective and competitive NMDA antagonist (Ki = 310 nM for inhibition of [3H]-CPP binding in rat brain). It is centrally active upon oral administration in vivo.

1: D/'Hooge R, Raes A, Hiramatsu M, Mori A, Van Bogaert PP, De Deyn PP. Effects of the competitive N-methyl-D-aspartate antagonist CGP 37849 and its ethylester CGP 39551 on N-methyl-D-aspartate-evoked whole-cell currents in cultured spinal neurones and on vestibular stimulation-induced seizures in EL mice. Arzneimittelforschung. 1998 Dec;48(12):1121-5. PubMed PMID: 9893924.
2: Velísek L, Vachová D, Mares P. Excitatory amino acid antagonists and pentylenetetrazol-induced seizures during ontogenesis. IV. Effects of CGP 39551. Pharmacol Biochem Behav. 1997 Mar;56(3):493-8. PubMed PMID: 9077588.
3: De Sarro G, De Sarro A, Ammendola D, Patel S. Lack of development of tolerance to anticonvulsant effects of two excitatory amino acid antagonists, CGP [corrected] 37849 and CGP 39551 in genetically epilepsy-prone rats. Brain Res. 1996 Sep 23;734(1-2):91-7. Erratum in: Brain Res 1997 Mar 7;750(1-2):329. PubMed PMID: 8896813.
4: Mennini T, Miari A, Presti ML, Rizzi M, Samanin R, Vezzani A. Adaptive changes in the NMDA receptor complex in rat hippocampus after chronic treatment with CGP 39551. Eur J Pharmacol. 1994 Dec 12;271(1):93-101. PubMed PMID: 7698217.
5: Dall/'Olio R, Facchinetti F, Contestabile A, Gandolfi O. Chronic neonatal blockade of N-methyl-D-aspartate receptor by CGP 39551 increases dopaminergic function in adult rat. Neuroscience. 1994 Nov;63(2):451-5. PubMed PMID: 7891857.
6: Facchinetti F, Dall/'Olio R, Ciani E, Sparapani M, Virgili M, Contestabile A. Long-lasting effects of chronic neonatal blockade of N-methyl-D-aspartate receptor through the competitive antagonist CGP 39551 in rats. Neuroscience. 1994 May;60(2):343-53. PubMed PMID: 7915409.
7: Pearce PC, Halsey MJ, Maclean CJ, Ward EM, Pearson J, Henley M, Meldrum BS. The orally active NMDA receptor antagonist CGP 39551 ameliorates the high pressure neurological syndrome in Papio anubis. Brain Res. 1993 Sep 17;622(1-2):177-84. PubMed PMID: 7902190.
8: Facchinetti F, Ciani E, Dall/'Olio R, Virgili M, Contestabile A, Fonnum F. Structural, neurochemical and behavioural consequences of neonatal blockade of NMDA receptor through chronic treatment with CGP 39551 or MK-801. Brain Res Dev Brain Res. 1993 Aug 20;74(2):219-24. PubMed PMID: 8104744.
9: Maj J, Rogóz Z, Skuza G. Central effects of CGP 37849 and CGP 39551, competitive NMDA receptor antagonists, in mice. Pol J Pharmacol. 1993 Jul-Aug;45(4):349-60. PubMed PMID: 7906989.
10: Czechowska G, Dziki M, Pietrasiewicz T, Kleinrok Z, Turski WA, Czuczwar SJ. Competitive antagonists of NMDA receptors, CGP 37849 and CGP 39551, enhance the anticonvulsant activity of valproate against electroconvulsions in mice. Eur J Pharmacol. 1993 Feb 23;232(1):59-64. PubMed PMID: 8096188.
11: Maj J, Skuza G, Rogóz Z. Some central effects of CGP 37849 and CGP 39551, the competitive NMDA receptor antagonists: potential antiparkinsonian activity. J Neural Transm Park Dis Dement Sect. 1993;6(1):53-62. PubMed PMID: 8105798.
12: Maj J, Rogóz Z, Skuza G, Sowińska H. The effect of CGP 37849 and CGP 39551, competitive NMDA receptor antagonists, in the forced swimming test. Pol J Pharmacol Pharm. 1992 Jul-Aug;44(4):337-46. PubMed PMID: 1363131.
13: Maren S, Baudry M, Thompson RF. Effects of the novel NMDA receptor antagonist, CGP 39551, on field potentials and the induction and expression of LTP in the dentate gyrus in vivo. Synapse. 1992 Jul;11(3):221-8. PubMed PMID: 1353274.
14: Virgili M, Migani P, Contestabile A, Barnabei O. Protection from kainic acid neuropathological syndrome by NMDA receptor antagonists: effect of MK-801 and CGP 39551 on neurotransmitter and glial markers. Neuropharmacology. 1992 May;31(5):469-74. PubMed PMID: 1356249.
15: Cotterell KL, Croucher MJ, Bradford HF. Weak anticonvulsant activity of CGP 37849 and CGP 39551 against kindled seizures following systemic administration. Eur J Pharmacol. 1992 Apr 22;214(2-3):285-7. PubMed PMID: 1355438.
16: Ylinen A, Lahtinen H, Sirviö J, Partanen J, Asikainen A, Gulyas A, Freund TF, Riekkinen P. Behavioural, electrophysiological and histopathological changes following sustained stimulation of the perforant pathway input to the hippocampus: effect of the NMDA receptor antagonist, CGP 39551. Brain Res. 1991 Jul 12;553(2):195-200. PubMed PMID: 1681982.
17: Chapman AG, Graham JL, Patel S, Meldrum BS. Anticonvulsant activity of two orally active competitive N-methyl-D-aspartate antagonists, CGP 37849 and CGP 39551, against sound-induced seizures in DBA/2 mice and photically induced myoclonus in Papio papio. Epilepsia. 1991 Jul-Aug;32(4):578-87. PubMed PMID: 1678345.
18: Löscher W, Hönack D, Fassbender CP. Regional alterations in brain amino acids after administration of the N-methyl-D-aspartate receptor antagonists MK-801 and CGP 39551 in rats. Neurosci Lett. 1991 Mar 11;124(1):115-8. PubMed PMID: 1677457.
19: Löscher W, Hönack D. Anticonvulsant and behavioral effects of two novel competitive N-methyl-D-aspartic acid receptor antagonists, CGP 37849 and CGP 39551, in the kindling model of epilepsy. Comparison with MK-801 and carbamazepine. J Pharmacol Exp Ther. 1991 Feb;256(2):432-40. PubMed PMID: 1671593.
20: Liljequist S. The competitive NMDA receptor antagonist, CGP 39551, inhibits ethanol withdrawal seizures. Eur J Pharmacol. 1991 Jan 3;192(1):197-8. PubMed PMID: 1674917.

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