title: Almotriptan, an antimigraine agent, and its malate salt.
abstract: The crystal structures of almotriptan {systematic name: N,N-dimethyl-2-[5-(pyrrolidin-1-ylsulfonylmethyl)-1H-indol-3-yl]ethanamine}, C17H25N3O2S, and almotriptan malate {systematic name: N,N-dimethyl-2-[5-(pyrrolidin-1-ylsulfonylmethyl)-1H-indol-3-yl]ethanaminium malate, C17H26N3O2S+ x C4H5O5(-), a novel selective serotonin 1B/D agonist, have been determined in order to gain further insight into the structure-activity relationships of triptans. The two structures differ in the orientation of their sulfonylpyrrolidine side chains. A comparison with other triptans reveals that molecules of almotriptan, sumatriptan, zolmitriptan and rizatriptan can adopt two principal conformations. N-H...N, N-H...O and O-H...O hydrogen bonds are responsible for the molecular packing.
authors.affiliation: Laboratory of X-ray Crystallography, Indian Institute of Chemical Technology, Hyderabad 500 007, India. sshiya@yahoo.com
authors.forename: K
authors.initials: K
authors.lastname: Ravikumar
authors.forename: B
authors.initials: B
authors.lastname: Sridhar
authors.forename: Harihara
authors.initials: H
authors.lastname: Krishnan
authors.forename: A N
authors.initials: AN
authors.lastname: Singh
mesh_terms: D018360:Crystallography, X-Ray; D006860:Hydrogen Bonding; D008293:Malates / Q000737:chemistry* / Q000627:therapeutic use; D008881:Migraine Disorders / Q000188:drug therapy; D008968:Molecular Conformation; D017366:Serotonin Receptor Agonists / Q000737:chemistry* / Q000627:therapeutic use; D013329:Structure-Activity Relationship; D014363:Tryptamines / Q000737:chemistry* / Q000627:therapeutic use
chemical_list: D008293:Malates; D017366:Serotonin Receptor Agonists; D014363:Tryptamines; C409045:almotriptan; C030298:malic acid