Chiral resolution and binding study of 1,3,4,14b-tetrahydro-2,10-dimethyl- 2H,10H-pyrazino[2,1-d]pyrrolo[1,2-b] [1,2,5]benzotriazepine (10-methyl-10- azaaptazepine) and 2-methyl-1,3,4,14b-tetrahydro-2H-pyrazino[2,1-d]pyrrolo[1,2- b] [1,2,5]benzothiadiazepine 10,10-dioxide (tiaaptazepine)

Gabriella De Martino, Giuseppe La Regina, Francesco La Torre, Roberto Cirilli, Ilario Mereghetti, Alfredo Cagnotto, Marino Artico, Romano Silvestri

Research output: Contribution to journalArticle

Abstract

The affinities of the enantiomers of 1,3,4,14b-tetrahydro-2,10-dimethyl-2H, 10H-pyrazino[2,1-d]pyrrolo[1,2-b] [1,2,5]benzotriazepine (10-methyl-10- azaaptazepine, 5) and 2-methyl-1,3,4,14b-tetrahydro-2H-pyrazino[2,1-d]pyrrolo[1, 2-b] [1,2,5]benzothiadiazepine 10,10-dioxide (tiaaptazepine, 6) were evaluated in receptor binding assays. Compound (+)-(S)-5, the most significant tested enantiomer, showed good affinities for 5-HT1A, 5-HT2A 5-HT2C and α2NA receptors, moderate affinities for DA1, DA3r and 5-HT3 receptors and it was devoid of affinity for DA2, α1NA and muscarinic receptors. Compound (+)-(S)-5 showed an interesting pharmacological profile different from those of the reference compounds mirtazepine, mianserin and 6-methoxymianserin.

Original languageEnglish
Pages (from-to)931-937
Number of pages7
JournalFarmaco
Volume60
Issue number11-12
DOIs
Publication statusPublished - Nov 2005

Keywords

  • 1,3,4,14b-Tetrahydro-2,10-dimethyl-2H,10H-pyrazino[2,1-d] pyrrolo[1,2-b] [1,2,5]benzotriazepine (10-methyl-10-azaaptazepine)
  • Chiral resolution

ASJC Scopus subject areas

  • Drug Discovery
  • Pharmaceutical Science

Fingerprint Dive into the research topics of 'Chiral resolution and binding study of 1,3,4,14b-tetrahydro-2,10-dimethyl- 2H,10H-pyrazino[2,1-d]pyrrolo[1,2-b] [1,2,5]benzotriazepine (10-methyl-10- azaaptazepine) and 2-methyl-1,3,4,14b-tetrahydro-2H-pyrazino[2,1-d]pyrrolo[1,2- b] [1,2,5]benzothiadiazepine 10,10-dioxide (tiaaptazepine)'. Together they form a unique fingerprint.

  • Cite this