Thioridazine hydrochloride

Thioridazine is an antipsychotic drug, used in the treatment of schizophrenia and psychosis, shows D4 selectivity or serotonin antagonism.

Thioridazine hydrochloride is a hydrochloride. It has a role as a first generation antipsychotic and a geroprotector. It contains a thioridazine.|A phenothiazine antipsychotic used in the management of PHYCOSES, including SCHIZOPHRENIA.

To a solution of 6f (200 mg, 0.371 mmol) in THF (10 mL, 100 mmol) at 0°C was added 2.0 M lithium aluminum hydride in THF (0.278 mL, 0.557 mmol). The reaction was warmed to room temperature and then heated at 50°C for 18 hours. At that time the reaction was cooled to 0°C and water, 1M sodium hydroxide and water were added. The mixture was stirred overnight and then filtered through a pad of Celite. The filtrate was concentrated under reduced pressure and the remaining residue purified by flash chromatography using 0-5percent methanol in DCM to afford the desired product (36 mg, 26percent) as a colorless oil. This oil was dissolved in ethanol and IM HCI, concentrated under reduced pressure and then concentrated from ethyl acetate twice to afford 7f as a white solid in quantitative yield.Chiral HPLC retention time: 12.85 min. NMR (400 MHz, MeOD) δ (ppm) = 1.48-1.58 (m, 2H), 1.70-2.10 (m, 6H), 2.51 (s, 3H), 2.69 (s, 3H), 2.97-3.17 (m, 2H), 3.37-3.47 (m, IH), 4.05-4.19 (m, 2H), 6.92-6.96 (m, 2H), 7.00-7.04 (m, IH), 7.08-7.10 (m, I H), 7.12-7.14 (m, IH), 7.20-7.23 (m, IH), 7.25- 7.29 (m, I H); MS (ESI+) for C21H26N2S2 m/z 371 (M+H) In an analogous manner, 6s (220 mg, 0.408 mmol) provided 7s (29 mg, 19percent) as a colorless oil. This oil was dissolved in ethanol and IM HCI, concentrated under reduced pressure and then concentrated from ethyl acetate twice to afford 7s as a white solid in quantitative yield.Chiral HPLC retention time: 12.1 1 min. NMR (400 MHz, MeOD) δ (ppm) - 1.48-1.58 (m, 2H), 1.70-2.10 (m, 6H), 2.51 (s, 3H), 2.69 (s, 3H), 2.97-3.17 (m, 2H), 3.37-3.47 (m, 1H), 4.05-4.19 (m, 2H), 6.92-6.96 (m, 2H), 7.00-7.04 (m, III), 7.08-7.10 (m, 1H), 7.12-7.14 (m, 1H), 7.20-7.23 (m, IH), 7.25- 7.29 (m, 1H); MS (ESI+) for C21H26N2S2 mtz 371 (M+H)

Thioridazine HCl is a dopamine receptor blocker and antipsychotic.It is the parent compound of sulforidazine and mesoridazine. This compound has been reported to bind strongly to dopamine receptors on cancer stem cells and cause differentiation leaving normal cells alone (see Can. Chem. News 12 July/August 2012).

Molecular Weight:407.0
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:4
Exact Mass:406.1304189
Monoisotopic Mass:406.1304189
Topological Polar Surface Area:57.1
Heavy Atom Count:26
Complexity:432
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:2
Compound Is Canonicalized:Yes