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Protonation of Trimipramine Salts of Maleate, Mesylate and Hydrochloride Observed by 1H, 13C and 15N NMR Spectroscopy

Protonation of Trimipramine Salts of Maleate, Mesylate and Hydrochloride Observed by 1H, 13C and 15N NMR Spectroscopy

B S Somashekar, G A Nagana Gowda, A R Ramesha, C L Khetrapal

Magn Reson Chem. 2005 Feb;43(2):166-70.

PMID: 15562517

Abstract:

Protonation of the tricyclic antidepressant drug trimipramine with maleic acid, methanesulfonic acid and hydrochloric acid was studied using 1H, 13C and 15N NMR spectroscopy at natural abundance. The effect of counter ions on the protonation was compared under identical conditions of solvent, concentration and temperature using homonuclear and heteronuclear one- and two-dimensional experiments. Differential protonation of the terminal tertiary amine nitrogen is determined from the indirect spin-spin couplings, chemical shifts, 13C relaxation data and variable-temperature experiments. In the maleate salt, only one of the acidic protons is involved in protonation, the other being associated with the anion moiety. 15N chemical shifts of the protonated nitrogens are nearly linearly related to the pK(a) of the constituent acid.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
IAR42410455	Kevetrin-(4-isothioureido-13C,15N2-butyronitrile-13C,15N) hydrochloride			Price

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