Last updated
Clinical data
ATC code
  • none
Legal status
Legal status
  • Development terminated
Pharmacokinetic data
Metabolism Hepatic
Elimination half-life 1.4 hours
Excretion Urine
  • 8-[4-[4-(1,2-benzothiazol-3-yl)piperazin-1-yl]butyl]-8-azaspiro[4.5]decane-7,9-dione
CAS Number
PubChem CID
CompTox Dashboard (EPA)
Chemical and physical data
Formula C24H32N4O2S
Molar mass 440.61 g·mol−1

Tiospirone (BMY-13,859), also sometimes called tiaspirone or tiosperone, is an atypical antipsychotic of the azapirone class. [1] It was investigated as a treatment for schizophrenia in the late 1980s and was found to have an effectiveness equivalent to those of typical antipsychotics in clinical trials but without causing extrapyramidal side effects. [2] [3] [4] [5] However, development was halted and it was not marketed. Perospirone, another azapirone derivative with antipsychotic properties, was synthesized and assayed several years after tiospirone. [6] It was found to be both more potent and more selective in comparison and was commercialized instead. [6]




Tiospirone acts as a 5-HT1A receptor partial agonist, 5-HT2A, 5-HT2C, and 5-HT7 receptor inverse agonist, and D2, D4, and α1-adrenergic receptor antagonist. [7] [8] [9] [10] [11] [12]

Binding profile [13]

ReceptorKi (nM)


Note that the piperazine used is the same as in the synthesis of Ziprasidone as well as Perospirone & 1192U90 [155289-31-9].

Synthesis: Patents: Tiospirone synthesis.svg
Synthesis: Patents:

Halogenation of 2,2'-dithiosalicylic acid [119-80-2] (1) with thionyl chloride gives 2,2'-dithiodibenzoyl chloride [19602-82-5] (2). Treatment with molecular chlorine then gives 2-(chlorothio)-benzoyl chloride [3950-02-5] (3). Treatment with ammonium hydroxide gives benzisothiazolone [2634-33-5] (4). Halogenation of the lactam with phosphoryl chloride gives 3-chloro-1,2-benzisothiazole [7716-66-7] (5). Alkylation of this with piperazine then yields 3-(1-piperazinyl)-1,2-benzisothiazole [87691-87-0] (6). The reaction of this with tetramethylenedibromide [110-52-1] (7) gave rise to CID:13232499 (8). The last step in the procedure is the reaction with azaspirodecanedione [1075-89-4] (9), thus completing the synthesis of tiaspirone (10).

See also

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