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Thioridazine hydrochloride

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Name

Thioridazine hydrochloride

EINECS 204-992-8
CAS No. 130-61-0 Density 1.1227 (rough estimate)
PSA 57.08000 LogP 6.69050
Solubility Soluble in water (75 mM), DMSO (100 mM), chloroform, ethanol, and methanol. Melting Point 158-160 °C
Formula C21H27ClN2S2 Boiling Point 515.7 °C at 760 mmHg
Molecular Weight 407.044 Flash Point 265.7 °C
Transport Information UN 3077 9/PG 3 Appearance Pale yellow solid
Safety 26-36-60-61 Risk Codes 22-36/37/38-50/53
Molecular Structure Molecular Structure of 130-61-0 (Thioridazine hydrochloride) Hazard Symbols HarmfulXn, DangerousN
Synonyms

10H-Phenothiazine,10-[2-(1-methyl-2-piperidinyl)ethyl]-2-(methylthio)-, monohydrochloride (9CI);Phenothiazine, 10-[2-(1-methyl-2-piperidyl)ethyl]-2-(methylthio)-,hydrochloride (6CI,7CI);Phenothiazine,10-[2-(1-methyl-2-piperidyl)ethyl]-2-(methylthio)-, monohydrochloride (8CI);10-[3-(1-Methyl-2-piperidyl)ethyl]-2-(methylthio)phenothiazine hydrochloride;2-Methylmercapto-10-[2-(N-methyl-2-piperidyl)ethyl]phenothiazine hydrochloride;Aldazine;Mallorol;Mellaril;Mellaril hydrochloride;Melleretten;Melleril (tablet);NSC 186060;Novoridazine;Orsanil;Stalleril;10-(2-(1-Methyl-2-piperidyl)ethyl)-2-methylthiophenothiazine hydrochloride;10H-Phenothiazine,10-[2-(1-methyl-2-piperidinyl)ethyl]-2-(methylthio)-, hydrochloride (1:1);

Article Data 2

Thioridazine hydrochloride Synthetic route

(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 2-{2-[2-(methylthio)-10H-phenothiazin-10-yl]ethyl}piperidine-1-carboxylate

130-61-0

thioridazine Hydrochloride

Conditions
ConditionsYield
Stage #1: (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 2-{2-[2-(methylthio)-10H-phenothiazin-10-yl]ethyl}piperidine-1-carboxylate With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 50℃; for 18h; Inert atmosphere;
Stage #2: With hydrogenchloride In ethanol; water
100%
Multi-step reaction with 2 steps
1: lithium aluminium tetrahydride / tetrahydrofuran / 18 h / 0 - 50 °C / Inert atmosphere
2: hydrogenchloride / ethanol; water
View Scheme
130-61-0

thioridazine Hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In ethanol; water100%
130-61-0

thioridazine Hydrochloride

969-99-3

chlorpromazine sulfoxide

Conditions
ConditionsYield
With dihydrogen peroxide In water for 72h; Ambient temperature;93%
50893-53-3

carbonochloridic acid 1-chloro-ethyl ester

130-61-0

thioridazine Hydrochloride

1-chloroethyl 2-(2-(2-(methylthio)-10hphenothiazin-10-yl)ethyl)piperidine-1-carboxylate

Conditions
ConditionsYield
Stage #1: thioridazine Hydrochloride With triethylamine In 1,2-dichloro-ethane at 20℃; for 0.333333h; Inert atmosphere;
Stage #2: carbonochloridic acid 1-chloro-ethyl ester In 1,2-dichloro-ethane for 12h; Inert atmosphere; Reflux;
84%
513-53-1

1-methyl-1-propanethiol

130-61-0

thioridazine Hydrochloride

96457-89-5

2-(sec-butylthio)-10-(2-(1-methylpiperidin-2-yl)ethyl)-10H-phenothiazine

Conditions
ConditionsYield
With Singacycle A1; lithium hexamethyldisilazane In o-xylene at 160℃; for 12h; Glovebox; Sealed tube;71%
1569-69-3

Cyclohexanethiol

130-61-0

thioridazine Hydrochloride

2-(cyclohexylthio)-10-(2-(1-methylpiperidin-2-yl)ethyl)-10H-phenothiazine

Conditions
ConditionsYield
With Singacycle A1; lithium hexamethyldisilazane In o-xylene at 160℃; for 12h; Glovebox; Sealed tube;62%
34301-54-7

1-Adamantanethiol

130-61-0

thioridazine Hydrochloride

2-((adamantan-1-yl)thio)-10-(2-(1-methylpiperidin-2-yl)ethyl)-10H-phenothiazine

Conditions
ConditionsYield
With Singacycle A1; lithium hexamethyldisilazane In o-xylene at 160℃; for 12h; Glovebox; Sealed tube;61%
130-61-0

thioridazine Hydrochloride

100-53-8

phenylmethanethiol

97013-68-8

2-(benzylthio)-10-(2-(1-methylpiperidin-2-yl)ethyl)-10H-phenothiazine

Conditions
ConditionsYield
With Singacycle A1; lithium hexamethyldisilazane In o-xylene at 160℃; for 12h; Glovebox; Sealed tube;56%
110-53-2

1-Bromopentane

130-61-0

thioridazine Hydrochloride

1-methyl-2-(2-(2-(methylthio)-10H-phenothiazin-10-yl)ethyl)-1-pentylpiperidin-1-ium bromide

Conditions
ConditionsYield
In acetonitrile for 24h; Reflux; Inert atmosphere;51%
111-88-6

Octanethiol

130-61-0

thioridazine Hydrochloride

10-(2-(1-methylpiperidin-2-yl)ethyl)-2-(octylthio)-10H-phenothiazine

Conditions
ConditionsYield
With Singacycle A1; lithium hexamethyldisilazane In o-xylene at 160℃; for 12h; Glovebox; Sealed tube;49%

Thioridazine hydrochloride Chemical Properties


IUPAC NAME: 10-[2-(1-Methylpiperidin-2-yl)ethyl]-2-methylsulfanylphenothiazine hydrochloride
EINECS: 204-992-8
Molecular Formula: C21H27ClN2S2
Molecular Weight: 407.04 g/mol
Flash Point: 265.7 °C
Boiling Point: 515.7 °C at 760 mmHg
Enthalpy of Vaporization: 78.76 kJ/mol 
Vapour Pressure: 9.65E-11 mmHg at 25 °C 
Appearance: Pale Yellow Solid
Melting Point: 158-160 °C
Product Categories: Miscellaneous ; Intermediates & Fine Chemicals ; Pharmaceuticals ; Dopamine receptor 
Classification Code of 10-(2-(1-Methyl-2-piperidyl)ethyl)-2-methylthiophenothiazine hydrochloride (CAS NO.130-61-0): Antipsychotic; Drug / Therapeutic Agent; Human Data; Mutation data; Sedative-hypnotic

Thioridazine hydrochloride Uses

 10-(2-(1-Methyl-2-piperidyl)ethyl)-2-methylthiophenothiazine hydrochloride (CAS NO.130-61-0) is used for acute schizophrenia, bipolar disorder, menopause, mental illness, nervous depression.

Thioridazine hydrochloride Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 oral 160mg/kg (160mg/kg)   "Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972Vol. -, Pg. 53, 1972.
mouse LD50 intraperitoneal 100mg/kg (100mg/kg)   National Technical Information Service. Vol. AD277-689,
mouse LD50 intravenous 33mg/kg (33mg/kg)   Therapie. Vol. 14, Pg. 793, 1959.
mouse LD50 oral 360mg/kg (360mg/kg)   "Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972Vol. -, Pg. 53, 1972.
rabbit LD50 intravenous 26mg/kg (26mg/kg)   "Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972Vol. -, Pg. 53, 1972.
rabbit LD50 oral 1100mg/kg (1100mg/kg)   "Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972Vol. -, Pg. 53, 1972.
rat LD50 intravenous 71mg/kg (71mg/kg)   "Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972Vol. -, Pg. 53, 1972.
rat LD50 oral 1060mg/kg (1060mg/kg)   Drugs in Japan Vol. 6, Pg. 458, 1982.
women TDLo oral 864mg/kg/18D- (864mg/kg) CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP

ENDOCRINE: EVIDENCE OF THYROID HYPERFUNCTION
Postgraduate Medical Journal. Vol. 60, Pg. 445, 1984.

Thioridazine hydrochloride Consensus Reports

EPA Genetic Toxicology Program.

Thioridazine hydrochloride Safety Profile

Poison by ingestion and intravenous routes. Human systemic effects: evidence of thyroid hyperfunction, increased body temperature, pulse rate increase. Mutation data reported. When heated to decomposition it emits very toxic fumes of NOx, SOx, and HCl.
Hazard Codes: HarmfulXn,DangerousN
Risk Statements:
R22: Harmful if swallowed.
R36/37/38: Irritating to eyes, respiratory system and skin.
R50/53: Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment.
Safety Statements:
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36: Wear suitable protective clothing.
S60: This material and its container must be disposed of as hazardous waste. 
S61: Avoid release to the environment. Refer to special instructions / safety data sheets.

Thioridazine hydrochloride Specification

 10-(2-(1-Methyl-2-piperidyl)ethyl)-2-methylthiophenothiazine hydrochloride (CAS NO.130-61-0), its Synonyms are Thioridazine hydrochloride ; 10H-Phenothiazine, 10-(2-(1-methyl-2-piperidinyl)ethyl)-2-(methylthio)-, monohydrochloride ; 2-Methylmercapto-10-(2-(N-methyl-2-piperidyl)ethyl)phenothiazine hydrochloride ; Mellaril ; Mellaril hydrochloride ; Melleril (tablet) ; Melzine ; Sonapax hydrochloride ; Thioridazine HCl ; Thioridazine chloride .

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