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Title: Solid-state and solution /sup 13/C NMR in the conformational analysis of methadone-hydrochloride and related narcotic analgesics

Abstract

Solid state and solution /sup 13/C NMR have been used to study the conformations of the racemic mixtures and single enantiomers of methadone hydrochloride, alpha and beta methadol hydrochloride, and alpha and beta acetylmethadol hydrochloride. The NMR spectra acquired for the compounds as solids, and in polar and nonpolar solvents are compared, in order to determine the conformation of the molecules in solution. To determine the reliability of assigning solution conformations by comparing solution and solid state chemical shift data, three bond coupling constants measured in solution are compared with those calculated from X-ray data. The conformations of the racemic mixture and plus enantiomer of methadone hydrochloride have been shown to be very similar in the solid state, where minor differences in conformation can be seen by comparing NMR spectra obtained for the solids. Also shown is that the molecules of methadone hydrochloride have conformations in polar and in nonpolar solvents which are very similar to the conformation of the molecules in the solid state.

Authors:
Publication Date:
Research Org.:
North Carolina State Univ., Raleigh (USA)
OSTI Identifier:
6592728
Alternate Identifier(s):
OSTI ID: 6592728
Resource Type:
Thesis/Dissertation
Resource Relation:
Other Information: Thesis (Ph. D)
Country of Publication:
United States
Language:
English
Subject:
59 BASIC BIOLOGICAL SCIENCES; ANALGESICS; MOLECULAR STRUCTURE; CARBON 13; CHEMICAL SHIFT; MOLECULES; NMR SPECTRA; NUCLEAR MAGNETIC RESONANCE; SOLID SOLUTIONS; CARBON ISOTOPES; CENTRAL NERVOUS SYSTEM DEPRESSANTS; DISPERSIONS; DRUGS; EVEN-ODD NUCLEI; ISOTOPES; LIGHT NUCLEI; MAGNETIC RESONANCE; MIXTURES; NUCLEI; RESONANCE; SOLUTIONS; SPECTRA; STABLE ISOTOPES 550200* -- Biochemistry

Citation Formats

Sumner, S.C.J. Solid-state and solution /sup 13/C NMR in the conformational analysis of methadone-hydrochloride and related narcotic analgesics. United States: N. p., 1986. Web.
Sumner, S.C.J. Solid-state and solution /sup 13/C NMR in the conformational analysis of methadone-hydrochloride and related narcotic analgesics. United States.
Sumner, S.C.J. Wed . "Solid-state and solution /sup 13/C NMR in the conformational analysis of methadone-hydrochloride and related narcotic analgesics". United States.
@article{osti_6592728,
title = {Solid-state and solution /sup 13/C NMR in the conformational analysis of methadone-hydrochloride and related narcotic analgesics},
author = {Sumner, S.C.J.},
abstractNote = {Solid state and solution /sup 13/C NMR have been used to study the conformations of the racemic mixtures and single enantiomers of methadone hydrochloride, alpha and beta methadol hydrochloride, and alpha and beta acetylmethadol hydrochloride. The NMR spectra acquired for the compounds as solids, and in polar and nonpolar solvents are compared, in order to determine the conformation of the molecules in solution. To determine the reliability of assigning solution conformations by comparing solution and solid state chemical shift data, three bond coupling constants measured in solution are compared with those calculated from X-ray data. The conformations of the racemic mixture and plus enantiomer of methadone hydrochloride have been shown to be very similar in the solid state, where minor differences in conformation can be seen by comparing NMR spectra obtained for the solids. Also shown is that the molecules of methadone hydrochloride have conformations in polar and in nonpolar solvents which are very similar to the conformation of the molecules in the solid state.},
doi = {},
journal = {},
number = ,
volume = ,
place = {United States},
year = {Wed Jan 01 00:00:00 EST 1986},
month = {Wed Jan 01 00:00:00 EST 1986}
}

Thesis/Dissertation:
Other availability
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