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

Thesis/Dissertation · Wed Jan 01 00:00:00 EST 1986

OSTI ID:6592728

Sumner, S C.J.

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.

• Research Organization: North Carolina State Univ., Raleigh (USA)
• OSTI ID: 6592728
• Resource Relation: Other Information: Thesis (Ph. D)
• Country of Publication: United States
• Language: English

Related Subjects

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