Ethyl beta-Carboline-3-carboxylate

Title: Ethyl b-Carboline-3-carboxylate
CAS Registry Number: 74214-62-3
CAS Name: 9H-Pyrido[3,4-b]indole-3-carboxylic acid ethyl ester
Additional Names: ethyl norharmancarboxylate; b-CCE
Molecular Formula: C14H12N2O2
Molecular Weight: 240.26
Percent Composition: C 69.99%, H 5.03%, N 11.66%, O 13.32%
Literature References: Deriv of b-carboline that is a potent displacer of 3H-diazepam from brain benzodiazepine receptors. Isoln from human urine and brain and binding site study: C. Braestrup et al., Proc. Natl. Acad. Sci. USA 77, 2288 (1980). Initially thought to be an endogenous ligand for benzodiazepine receptors in mammalian CNS, it is now believed to be formed during isoln and extraction procedures, R. F. Squires in GABA and Benzodiazepine Receptors, E. Costa et al., Eds. (Raven Press, New York, 1980) pp 129-138; M. Nielson et al., J. Neurochem. 36, 276 (1981). Synthesis and psychotropic activity: JP Kokai 81 43283 (to Schering AG), C.A. 95, 115508a (1981); U. Eder et al., EP 30254 (1981 to A/S Ferrosan; Schering AG). b-CCE has been shown to lower seizure threshold and to reverse the sedative effect of flurazepam, q.v.: P. J. Cowen et al., Nature 290, 54 (1981). Neurochemical and pharmacological actions of b-CCE and other b-carbolines: M. Cain et al., J. Med. Chem. 25, 1081 (1982). Anxiogenic and convulsant properties: L. Prado de Carvalho et al., Nature 301, 64 (1983).
Properties: mp 229-233°. uv max (pH 7): 215, 242, 279 nm.
Melting point: mp 229-233°
Absorption maximum: uv max (pH 7): 215, 242, 279 nm
Derivative Type: 3-Hydroxymethyl-b-carboline
CAS Registry Number: 65474-79-5
CAS Name: 9H-Pyrido[3,4-b]indole-3-methanol
Additional Names: 3-HMC
Molecular Formula: C12H10N2O
Molecular Weight: 198.22
Percent Composition: C 72.71%, H 5.08%, N 14.13%, O 8.07%
Literature References: Prepn: F. Hamaguchi, S. Ohki, Heterocycles 8, 383 (1977); M. Cain et al., loc. cit. Antagonism of anticonvulsant and anxiolytic actions of diazepam: P. Skolnick et al., Eur. J. Pharmacol. 68, 381 (1980).
Properties: Crystals, mp 225-228°.
Melting point: mp 225-228°
Use: As tools for studying benzodiazepine receptors.
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