9051. Tandospirone

Nomenclature

CAS number: 87760-53-0
(3aα,4β,7β,7aα)-Hexahydro-2-[4-[4-(2-pyrimidinyl)-1-piperazinyl]butyl]-4,7-methano-1H-isoindole-1,3(2H)-dione; (1R*,2S*,3R*,4S*)-N-[4-[4-(2-pyrimidinyl)-1-piperazinyl]butyl]-2,3-bicyclo[2.2.1]heptanedicarboximide.
C21H29N5O2; mol wt 383.49.
C 65.77%, H 7.62%, N 18.26%, O 8.34%.

Description and references

Serotonin (5-HT1A) receptor agonist. Prepn: K. Ishizumi et al., EP 82402; eidem, US 4507303 (1983, 1985 both to Sumitomo); idem et al., Chem. Pharm. Bull. 39, 2288 (1991). Behavioral pharmacology: C. A. Sannerud et al., Drug Alcohol Depend. 32, 195 (1993). Clinical efficacy in treatment of bulimia: H. Tamai et al., Int. J. Obes. 14, 289 (1990). Clinical evaluation of potential adverse effects: M. Suzuki et al., Jpn. J. Psychopharmacol. 13, 213 (1993); of abuse liability: S. M. Evans et al., J. Pharmacol. Exp. Ther. 271, 683 (1994). Review of pharmacology: P. A. Seymour et al., Prog. Clin. Biol. Res. 361, 453-460 (1990).

Chemical structure

Properties

Crystals from toluene/n-hexane, mp 112-113.5°.

Derivative

Citrate.

Nomenclature

CAS number: 112457-95-1
SM-3997; Sediel (Sumitomo).
C21H29N5O2.C6H8O7; mol wt 575.61.
C 56.34%, H 6.48%, N 12.17%, O 25.02%.

Properties

mp 169.5-170°.

Derivative

Hydrochloride.
C21H29N5O2.HCl; mol wt 419.95.
C 60.06%, H 7.20%, N 16.68%, O 7.62%, Cl 8.44%.

Properties

Crystals from isopropanol, mp 227-229°.

Therapeutic Category

Anxiolytic; antidepressant.

Keywords

Antidepressant; Anxiolytic; Arylpiperazines; Serotonin Receptor Agonist