130-61-0 Usage
Uses
1. Used in Pharmaceutical Industry:
Thioridazine hydrochloride is used as a dopamine receptor blocker and antipsychotic agent for the treatment of various psychiatric disorders. Its high anticholinergic activity and low EPS tendency make it a suitable choice for managing symptoms without causing significant side effects.
2. Used in Research and Development:
Thioridazine hydrochloride is used as an intercalating agent for analyzing the integrity of double-stranded DNA (dsDNA) using square-wave voltammetry (SWV) techniques. This application aids in understanding the structural and functional properties of DNA.
3. Used in Drug Metabolism Studies:
Thioridazine hydrochloride is used as a positive control for the inhibition of hepatic enzyme cytochrome P4502D6 (CYP2D6) in human liver microsomes. This helps researchers study the effects of various substances on the enzyme's activity and their potential interactions with drugs metabolized by CYP2D6.
4. Used in Cancer Research:
Thioridazine hydrochloride has been reported to bind strongly to dopamine receptors on cancer stem cells, causing differentiation and leaving normal cells unaffected. This property makes it a potential candidate for targeted cancer therapy, specifically against cancer stem cells.
5. Used in Chemical Synthesis:
As the parent compound of sulforidazine and mesoridazine, Thioridazine hydrochloride serves as a starting material for the synthesis of these related compounds, which also have pharmaceutical applications.
Originator
Mellaril,Sandoz,US,1959
Manufacturing Process
N-(m-methylmercapto-phenyl)-aniline (MP 59° to 61°C) is prepared by
condensing m-methylmercapto-aniline (BP 163° to 165°C/16 mm Hg) with the
potassium salt of o-chloro-benzoic acid and decarboxylating the resultant N-
(m-methylmercapto-phenyl)-anthranilic acid (MP 139° to 141°C) by heating,
and then distilling.9.87 parts of N-(m-methylmercapto-phenyl)-aniline are heated with 2.93
parts of sulfur and 0.15 part of powdered iodine for 15 minutes in a bath at
about 160°C. Upon termination of the ensuing evolution of hydrogen sulfide,
animal charcoal is added to the reaction mixture and recrystallization carried
out first from 40 parts by volume of chlorobenzene, and then from 25 to 30
parts by volume of benzene at the boiling temperature. The obtained citronyellow
3-methylmercapto-phenothiazine has a MP of 138° to 140°C.17.82 parts of 2-methylmercapto-phenothiazine, 3.4 parts of finely pulverized sodamide and 80 parts by volume of absolute xylene are heated to boiling for
two hours at a bath temperature of 180°C under a reflux condenser and while
stirring the reaction mixture. Without interrupting the heating, a solution of
13.2 parts of 2-(N-methyl-piperidyl-2')-1chloro-ethane in 40 parts by volume
of absolute xylene is then added dropwise in the course of 1 1/2 hours. After
further heating for 3 hours, the reaction mixture is cooled and, after the
addition of 5 parts of ammonium chloride, is shaken three times with water,
using 25 parts by volume each time. The xylene solution is extracted once
with 35 parts by volume of 3 normal acetic acid and then three times, each
time with 15 parts by volume of the said acid, after which the acetic acid
extract is washed with 60 parts by volume of ether and is then made
phenolphthalein-alkaline by means of 25 parts by volume of concentrated
aqueous caustic soda solution.The precipitated oily base is taken up in a total of 100 parts by volume of
benzene. The benzene layer, dried over potassium carbonate, is filtered and
then evaporated under reduced pressure. The residue from the evaporation is
distilled in a high vacuum; after separating a preliminary distillate which
passes over up to 228°C under a pressure of 0.92 mm Hg, the principal
fraction, 2-methylmercapto-10-[2'-(N-methyl-piperidyl-2'')-ethyl-
1']phenothiazine, which distills over at 228° to 232°C under the lastmentioned
pressure, is collected. The analytically pure base has a BP of
230°C/0.02 mm Hg.
Therapeutic Function
Tranquilizer
Biological Activity
Dopamine receptor antagonist that displays antipsychotic activity.
Biochem/physiol Actions
D2 dopamine receptor antagonist; phenothazine antipsychotic with reduced extrapyramidal side effects; Ca2+ channel blocker.
Check Digit Verification of cas no
The CAS Registry Mumber 130-61-0 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,3 and 0 respectively; the second part has 2 digits, 6 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 130-61:
(5*1)+(4*3)+(3*0)+(2*6)+(1*1)=30
30 % 10 = 0
So 130-61-0 is a valid CAS Registry Number.
InChI:InChI=1/C21H26N2S2.ClH/c1-22-13-6-5-7-16(22)12-14-23-18-8-3-4-9-20(18)25-21-11-10-17(24-2)15-19(21)23;/h3-4,8-11,15-16H,5-7,12-14H2,1-2H3;1H
130-61-0Relevant academic research and scientific papers
THE (S)-ENANTIOMER OF MEPAZINE
-
Page/Page column 47; 49; 50, (2015/01/16)
The present invention relates to the (S)-enantiomer of mepazine, its applicability in therapy, a pharmacological composition comprising (S)-mepazine, and processes for the preparation of (S)- mepazine and one of its intermediates.
Structural analysis of phenothiazine derivatives as allosteric inhibitors of the MALT1 paracaspase
Schlauderer, Florian,Lammens, Katja,Nagel, Daniel,Vincendeau, Michelle,Eitelhuber, Andrea C.,Verhelst, Steven H. L.,Kling, Dale,Chrusciel, Al,Ruland, Juergen,Krappmann, Daniel,Hopfner, Karl-Peter
supporting information, p. 10384 - 10387 (2013/10/21)
Second site: In the crystal structure of human MALT1casp-Ig3 (mucosa-associated lymphoid tissue lymphoma translocation protein 1) in complex with the tricyclic phenothiazine derivative thioridazine (violet in the picture), the inhibitor is bound in a hydrophobic pocket far from the active site. This explains the action of phenothiazine derivatives as noncompetitive, reversible inhibitors. Copyright
![(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 2-{2-[2-(methylthio)-10H-phenothiazin-10-yl]ethyl}piperidine-1-carboxylate](/Databaselist/images/loading.webp)
