title: Frovatriptan salts of aliphatic carboxylic acids.
abstract: 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.
authors.affiliation: Centre for X-ray Crystallography, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, India. sshiya@yahoo.com
authors.forename: Krishnan
authors.initials: K
authors.lastname: Ravikumar
authors.forename: Balasubramanian
authors.initials: B
authors.lastname: Sridhar
authors.forename: Jagadeesh Babu
authors.initials: JB
authors.lastname: Nanubolu
authors.forename: Venkatasubramanian
authors.initials: V
authors.lastname: Hariharakrishnan
authors.forename: Bandi Venugopal
authors.initials: BV
authors.lastname: Rao
mesh_terms: D000838:Anions / Q000737:chemistry; D002227:Carbazoles / Q000737:chemistry*; D002264:Carboxylic Acids / Q000737:chemistry*; D002412:Cations / Q000737:chemistry; D018360:Crystallography, X-Ray; D005227:Fatty Acids / Q000737:chemistry*; D006860:Hydrogen Bonding; D015394:Molecular Structure; D012492:Salts / Q000737:chemistry*; D014363:Tryptamines / Q000737:chemistry*
chemical_list: D000838:Anions; D002227:Carbazoles; D002264:Carboxylic Acids; D002412:Cations; D005227:Fatty Acids; D012492:Salts; D014363:Tryptamines; C108128:frovatriptan