Title: Dizocilpine
CAS Registry Number: 77086-21-6
CAS Name: 10,11-Dihydro-5-methyl-5H-dibenzo[a,d]cyclohepten-5,10-imine
Additional Names: (+)-5-methyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5,10-imine
Molecular Formula: C16H15N
Molecular Weight: 221.30
Percent Composition: C 86.84%, H 6.83%, N 6.33%
Literature References: Non-competitive NMDA, q.v., receptor antagonist. Prepn of racemate: M. E. Christy et al., J. Org. Chem. 44, 3117 (1979); T. R. Lamanec et al., ibid. 53, 1768 (1988); and of enantiomers: BE 882361; P. Anderson et al., US 4399141 (1980, 1983 both to Merck & Co.). Series of papers on pharmacological activities: B. V. Clineschmidt et al., Drug Dev. Res. 2, 123-163 (1982). NMDA receptor binding studies: E. H. F. Wong et al., Proc. Natl. Acad. Sci. USA 83, 7104 (1986); A. C. Foster, E. H. F. Wong, Br. J. Pharmacol. 91, 403 (1987); J. E. Huettner, B. P. Bean, Proc. Natl. Acad. Sci. USA 85, 1307 (1988). Metabolism in animals: H. B. Hucker et al., Drug Metab. Dispos. 11, 54 (1983). Pharmacokinetics: A. S. Troupin et al., Curr. Probl. Epilepsy 4, 191 (1986). Protective effects against excitotoxic amino acid-induced neuronal degeneration: G. N. Woodruff et al., Neuropharmacology 26, 903 (1987); A. C. Foster et al., Neurosci. Lett. 76, 307 (1987); A. C. Foster et al., J. Neurosci. 8, 4745 (1988); specifically in ischemia: R. Gill et al., Neuroscience 25, 847 (1988); E. Ozyurt et al., J. Cereb. Blood Flow Metab. 8, 138 (1988). Anticonvulsant activity in models of epilepsy: K. Sato et al., Brain Res. 463, 12 (1988); M. E. Gilbert, ibid. 90. Clinical evaluation in attention deficit disorder: F. W. Reimherr et al., Psychopharmacol. Bull. 22, 237 (1986).
Properties: White solid from cyclohexane, mp 68.5-69°. [a]20589 +161.4° (c = 0.038 g/2 ml ethanol).
Melting point: mp 68.5-69°
Optical Rotation: [a]20589 +161.4° (c = 0.038 g/2 ml ethanol)
Derivative Type: Maleate
CAS Registry Number: 77086-22-7
Manufacturers' Codes: MK-801
Molecular Formula: C16H15N.C4H4O4
Molecular Weight: 337.37
Percent Composition: C 71.20%, H 5.68%, N 4.15%, O 18.97%
Properties: Crystalline solid, mp 208.5-210°. [a]D20 +114° (c = 0.0128 g/2 ml ethanol).
Melting point: mp 208.5-210°
Optical Rotation: [a]D20 +114° (c = 0.0128 g/2 ml ethanol)
Derivative Type: (-)-Form
CAS Registry Number: 77086-19-2
Properties: White solid from cyclohexane, mp 68.5-69.5°. [a]589 -160.8° (c = 0.032 g/2 ml ethanol).
Melting point: mp 68.5-69.5°
Optical Rotation: [a]589 -160.8° (c = 0.032 g/2 ml ethanol)
Use: Biochemical probe for NMDA receptors. |