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Frovatriptan salts of aliphatic carboxylic acids

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The interaction of the antimigraine pharmaceutical agent frovatriptan with acetic acid and succinic acid yields the salts (±)‐6‐carbamoyl‐N‐methyl‐2,3,4,9‐tetrahydro‐1H‐carbazol‐3‐aminium acetate, C14H18N3O+·C2H3O2 , (I), (R)‐(+)‐6‐carbamoyl‐N‐methyl‐2,3,4,9‐tetrahydro‐1H‐carbazol‐3‐aminium 3‐carboxypropanoate monohydrate, C14H18N3O+·C4H5O4 ·H2O, (II), and bis[(R)‐(+)‐6‐carbamoyl‐N‐methyl‐2,3,4,9‐tetrahydro‐1H‐carbazol‐3‐aminium] succinate trihydrate, 2C14H18N3O+·C4H4O4 2−·3H2O, (III). The methylazaniumyl substitutent is oriented differently in all three structures. Additionally, the amide group in (I) is in a different orientation. All the salts form three‐dimensional hydrogen‐bonded structures. In (I), the cations form head‐to‐head hydrogen‐bonded amide–amide catemers through N—H...O interactions, while in (II) and (III) the cations form head‐to‐head amide–amide dimers. The cation catemers in (I) are extended into a three‐dimensional network through further interactions with acetate anion acceptors. The presence of succinate anions and water molecules in (II) and (III) primarily governs the three‐dimensional network through water‐bridged cation–anion associations via O—H...O and N—H...O hydrogen bonds. The structures reported here shed some light on the possible mode of noncovalent interactions in the aggregation and interaction patterns of drug molecule adducts.
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Document Type: Research Article

Publication date: April 15, 2013

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