Structural studies of analgesics and their interactions. III. The crystal and molecular structure of amidopyrine

Singh, TP and Vijayan, M (1976) Structural studies of analgesics and their interactions. III. The crystal and molecular structure of amidopyrine. In: Acta Crystallographica Section B: Structural Crystallography and Crystal Chemistry, 32 (8). pp. 2432-2437.

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Abstract

Amidopyrine (1-phenyl-2,3-dimethyl-4-dimethylaminopyrazolone), C13HzvN30, a dimethylamino derivative of antipyrine and an important analgesic and antipyretic agent, crystallizes in the triclinic space group P1 with four molecules in a unit cell of dimensions a= 7.458 (5), b = 10.744 (5), c= 17.486 (15)/~,, e=98.6 (2),/~= 85.6 (3), y= 108-6 (2) . The structure was solved by direct methods and refined to an R value of 0.055 for 3706 photographically observed reflexions. The dimensions of the two crystallographically independent molecules are very nearly the same. The pyrazolone moiety in the molecule has dimensions comparable to those in antipyrine. Unlike antipyrine, the molecular dimensions of amidopyrine in the free state (the present structure) are close to those found in some of its hydrogenbonded complexes. Thus it appears that the presence of the dimethylamino group makes the molecule more resistant to changes in its dimensions resulting from molecular association. An attempt has also been made to correlate the polar nature of the pyrazolone moiety and the hybridization state of the hetero nitrogen atoms in antipyrine, amidopyrine and their complexes.

Item Type:	Journal Article
Publication:	Acta Crystallographica Section B: Structural Crystallography and Crystal Chemistry
Publisher:	International Union of Crystallography
Additional Information:	Copyright of this article belongs to International Union of Crystallography
Department/Centre:	Division of Biological Sciences > Molecular Biophysics Unit
Date Deposited:	09 Dec 2009 10:28
Last Modified:	19 Sep 2010 05:49
URI:	http://eprints.iisc.ac.in/id/eprint/24270

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