Synthesis of isotopically labeled CIS-(3aR)-(-)-2,3,3a,4,5,9b-hexahydro-3-(N-propyl)-1H-benz[e]indole-9-carboxamide, a 5-HT1A receptor agonist

• Published in: Journal of labelled compounds & radiopharmaceuticals Vol. 39; no. 11; pp. 891 - 900
• Main Authors: Stolle, Wayne T., Easter, John A., Ackland, Mark J., Haadsma-Svensson, Susanne R., Lin, Chiu-Hong, Hsi, Richard S. P.
• Format: Journal Article
• Language: English
• Published: Chichester John Wiley & Sons, Ltd 01.11.1997; Wiley
• Subjects: aryl cyanation; Biochemical Research Methods; Biochemistry & Molecular Biology; Biological and medical sciences; C-13; C-14; catalytic reduction; Chemistry; Chemistry, Analytical; Chemistry, Medicinal; Exact sciences and technology; Heterocyclic compounds; Heterocyclic compounds with only one n hetero atom and condensed derivatives; isotopic labeling; Life Sciences & Biomedicine; Medical sciences; N-15; Neuropharmacology; O-18; Organic chemistry; Pharmacology & Pharmacy; Pharmacology. Drug treatments; Physical Sciences; Preparations and properties; Psycholeptics: tranquillizer, neuroleptic; Psychology. Psychoanalysis. Psychiatry; Psychopharmacology; Science & Technology; synthesis; tritium; synthesis; aryl cyanation; O-18; tritium; catalytic reduction; C-14; isotopic labeling; C-13; CIS-(3AR)-(-)-2,3,3A,4,5,9B-HEXAHYDRO-3-PROPYL-1H-BENZINDOLE-9-CARBOXAMIDE; N-15; DERIVATIVES; Agonist; Nitrogen 15; Isotope labelling; Radiolabelling; Nitrogen heterocycle; Oxygen 18; Psychotropic; Tritium; Hydrogen Isotopes; Tricyclic compound; Cis stereoisomer; Tranquillizer; Carboxamide; Aromatic compound; Carbon 14; Carbon 13; 5-HT1A receptor; Enantiomer(-)
• ISSN: 0362-4803; 1099-1344
• DOI: 10.1002/(SICI)1099-1344(199711)39:11<891::AID-JLCR34>3.0.CO;2-Q

The title compound is a potent and selective 5‐HT1A receptor agonist with clinical potentials for treating anxiety and depression. It has been labeled with stable and radioactive isotopes to support ADME studies in animals and human subjects. Its carboxamide group was labeled with C‐14, C‐13, or C‐13, N‐15, and O‐18. To provide a radioligand for investigating the receptor binding characteristics of the compound, we also labeled it with tritium in the N‐propyl group to obtain the high specific activity of 86.7 Ci/mmol. © 1997 John Wiley & Sons, Ltd.