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Methanesulfonic Acid Salt Forms of Carbamazepine and 10,11-dihydrocarbamazepine

Methanesulfonic Acid Salt Forms of Carbamazepine and 10,11-dihydrocarbamazepine

Alex R Eberlin, Mark D Eddleston, Christopher S Frampton

Acta Crystallogr C. 2013 Nov;69(Pt 11):1260-6.

PMID: 24192169

Abstract:

New methanesulfonic acid salt forms of the anticonvulsant and analgesic active pharmaceutical ingredient carbamazepine and its closely related structural analogue 10,11-dihydrocarbamazepine have been prepared and characterized by single-crystal X-ray diffraction at 120 and 100 K, respectively {namely [(5H-dibenzo[b,f]azepin-5-yl)(hydroxy)methylidene]azanium methanesulfonate, C15H13N2O(+)·CH3SO3(-), and [(10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)(hydroxy)methylidene]azanium methanesulfonate, C15H15N2O(+)·CH3SO3(-)}. In light of the structural information obtained, the crystal structure of the carbamazepine trifluoroacetic acid monosolvate [dibenzo[b,f]azepine-5-carboxamide-trifluoroacetic acid (1/1), C15H12N2O·CF3COOH] was redetermined at 100 and 270 K, and from this data it was concluded that the protonation state for this solvate species is best described as in an `intermediate state' with the acidic proton located almost at the mid-point between the acid and base.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP3564736-A	10,11-Dihydrocarbamazepine		3564-73-6	Price

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