Detail of "1207-72-3"

Reference

Photoelectron spectra of psychotropic drugs

Photoelectron spectra of psychotropic drugs. 2. Phenothiazine and related tranquilizers. Domelsmith, L. N.; Munchausen, Linda L.; Houk, K. N. (Dep. Chem., Louisiana State Univ., Baton Rouge, La., USA). J. Am. Chem. Soc., 99(20), 6506-14 (English) 1977. CODEN: JACSAT. DOCUMENT TYPE: Journal CA Section: 1 (Pharmacodynamics) Section cross-reference(s): 73, 22 Photoelectron spectra of phenothiazine (I) [92-84-2], N-methylphenothiazine [1207-72-3] and four biol. active derivs. - promazine [58-40-2], chlorpromazine [50-53-3], thioridazine [50-52-2], and tri fluoperazine [117-89-5] - were measured. Assignments of various ionization potentials (IP's) to particular MOs have been made on the basis of qual. models, correlations with IP's of similar mols., substituent effects, and CNDO/2 calcns. In contrast to previous deductions from calcns., soln. oxidn. potentials, or charge transfer spectra, these studies show that N-alkylation of I lowers the first, as well as higher, .pi. ionization potentials: I (1P1 = 7.26 eV), N-methylphenothiazine (7.15 eV), and promazine (7.20 eV). The discrepancies between gas-phase ionization potentials and soln. oxidn. potential and charge-transfer studies are attributed to differential solvation effects rather than conformational effects. There are also significant discrepancies between ionization potentials measured here and orbital energies obtained by CNDO/2 and ab initio calcns. The first ionization potentials, as well as averages of the first five .pi. ionization potentials, for the pharmacol. active phenothiazines fall in the order trifluoperazine (7.31 eV), promazine (7.20 eV), chlor promazine (7.16 eV), and thioridazine (7.00 eV) and do not correlate with antipsychotic activity based on dosage data for man.

A new study of the electrochemical oxidation of the phenothiazine ring

A new study of the electrochemical oxidation of the phenothiazine ring. I. The case of phenothiazine and its 3 and 7 disubstituted derivatives. Cauquis, Georges; Deronzier, Alain; Lepage, Jean Luc; Serve, Denis (Dep. Rech. Fondam., CEN Grenoble, Grenoble, Fr.). Bull. Soc. Chim.There are some reagents like 1771-23-9 is used in this study. Fr., (3-4, Pt. 2), 295-302 (French) 1977. CODEN: BSCFAS. DOCUMENT TYPE: Journal CA Section: 72 (Electrochemistry) Section cross-reference(s): 28, 22 The anodic processes of some 3,7-disubstituted phenothiazines and of N-methylphenothiazine [1207-72-3] in various acidic and alk. media in MeCN were studied. Depending on the medium, the oxidn. of the N-unsubstituted phenothiazines, which enclose the NH group, allows one to observe as a rule 6 species. In alk. medium, a 1-electron transfer results in the neutral free radical which, in some cases, dimerizes to give just the 1,10'- and 3,10'-biphenothiazinyls. The other species produced in acidic media are sufficiently stable to be unambiguously characterized. The oxidn. mechanism which is an EEC one in acidic media becomes progressively an ECE and a CEE one when increasing the basicity. The N-methylphenothiazine gives the sulfoxide through the radical cation. This sulfoxide is also oxidized to give the disulfoxide of a biphenothiazinyl. .