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CAS No.: | 113-59-7 |
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Name: | Chlorprothixene |
Molecular Structure: | |
Formula: | C18H18ClNS |
Molecular Weight: | 315.867 |
Synonyms: | 1-Propanamine,3-(2-chloro-9H-thioxanthen-9-ylidene)-N,N-dimethyl-, (Z)-;Thioxanthene-D9,g-propylamine, 2-chloro-N,N-dimethyl-, (Z)-(6CI,7CI,8CI);CPT;CPX;Chlorprothixene;Chlorprotixen;Chlorprotixene;Chlothixen;Iaractan;MK 184;Paxyl;Ro 4-0403;Tactaran;Taractan;Tarasan;Traquilan;Trictal;Truxil;Vetacalm;cis-Chlorprothixene;(3Z)-3-(2-chloro-9H-thioxanthen-9-ylidene)-N,N-dimethylpropan-1-amine;(Z)-2-Chloro-9-(3'-dimethylaminopropylidene)thioxanthene;(Z)-2-Chloro-N,N-dimethylthioxanthene-D9,g-propylamine;1-Propanamine, 3- (2-chloro-9H-thioxanthen-9-ylidene)-N,N-dimethyl-, (Z)-;1-propanamine, 3-(2-chloro-9H-thioxanthen-9-ylidene)-N,N-dimethyl-, (3Z)-;Chlorprothixene;Tarasan;Taractan; |
EINECS: | 204-032-8 |
Density: | 1.255 g/cm3 |
Melting Point: | 97-98° |
Boiling Point: | 435 °C at 760 mmHg |
Flash Point: | 216.9 °C |
Solubility: | 385.8ug/L(22.5 oC) |
PSA: | 28.54000 |
LogP: | 5.18800 |
chlorprothixene
Conditions | Yield |
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With sodium hydroxide In water |
Conditions | Yield |
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With C17H24N5Ru(1+)*F6P(1-); potassium acetate; potassium carbonate In 1-methyl-pyrrolidin-2-one at 35℃; for 48h; Inert atmosphere; | 90% |
trimethyl(difluoromethyl)silane
chlorprothixene
Conditions | Yield |
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With dicyclohexyl-(2′,4′,6′-triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine; cesium fluoride; bis(dibenzylideneacetone)-palladium(0) In 1,4-dioxane at 100℃; for 16h; Reagent/catalyst; Glovebox; Sealed tube; | 38% |
Conditions | Yield |
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With water In acetonitrile Quantum yield; Mechanism; Reagent/catalyst; Photolysis; Inert atmosphere; |
The Tarasan, with the CAS registry number 113-59-7 and EINECS registry number 204-032-8, has the systematic name of (3Z)-3-(2-chloro-9H-thioxanthen-9-ylidene)-N,N-dimethylpropan-1-amine. It is a kind of pale yellow crystalline powder, and insoluble in ethanol, ether or chloroform. The molecular formula of this chemical is C18H18ClNS.
The physical properties of Tarasan are as following: (1)ACD/LogP: 6.05; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 3.08; (4)ACD/LogD (pH 7.4): 4.41; (5)ACD/BCF (pH 5.5): 25.08; (6)ACD/BCF (pH 7.4): 529.41; (7)ACD/KOC (pH 5.5): 50.09; (8)ACD/KOC (pH 7.4): 1057.23; (9)#H bond acceptors: 1; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 3; (12)Polar Surface Area: 28.54 Å2; (13)Index of Refraction: 1.682; (14)Molar Refractivity: 95.35 cm3; (15)Molar Volume: 251.4 cm3; (16)Polarizability: 37.8×10-24cm3; (17)Surface Tension: 54.8 dyne/cm; (18)Density: 1.255 g/cm3; (19)Flash Point: 216.9 °C; (20)Enthalpy of Vaporization: 69.12 kJ/mol; (21)Boiling Point: 435 °C at 760 mmHg; (22)Vapour Pressure: 9.06E-08 mmHg at 25°C.
Preparation of Tarasan: It can start from 2-chlorothixantone. 2-Chlorothioxantone is reacted as a carbonyl component with either 3-dimethylaminopropylmagnesiumbromide, or with allylmagnesiumbromide, giving the corresponding tertiary alcohol. Dehydration is accomplished by acylation of the tertiary hydroxyl group using acetyl chloride and the subsequent pyrolysis of the formed acetate, which leads to the desired chlorprothixene which is also known as Tarasan.
Uses of Tarasan: It is a typical antipsychotic drug of the thioxanthene class. It is used in the teatment of psychotic disorders and of acute mania occurring as part of bipolar disorders. It is also used for the pre- and postoperative states with anxiety and insomnia, severe nausea/emesis.
You can still convert the following datas into molecular structure:
(1)SMILES: Clc2cc1C(\c3c(Sc1cc2)cccc3)=C/CCN(C)C
(2)InChI: InChI=1/C18H18ClNS/c1-20(2)11-5-7-14-15-6-3-4-8-17(15)21-18-10-9-13(19)12-16(14)18/h3-4,6-10,12H,5,11H2,1-2H3/b14-7-
(3)InChIKey: WSPOMRSOLSGNFJ-AUWJEWJLBL
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
man | LDLo | oral | 7mg/kg (7mg/kg) | BEHAVIORAL: GENERAL ANESTHETIC BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) BEHAVIORAL: MUSCLE WEAKNESS | Arzneimittel-Forschung. Drug Research. Vol. 14, Pg. 596, 1964. |
mouse | LD50 | intraperitoneal | 56200ug/kg (56.2mg/kg) | Cancer Research. Vol. 47, Pg. 5944, 1987. | |
mouse | LD50 | intravenous | 36mg/kg (36mg/kg) | Drugs in Japan Vol. -, Pg. 373, 1990. | |
mouse | LD50 | oral | 50100ug/kg (50.1mg/kg) | Cancer Research. Vol. 47, Pg. 5944, 1987. | |
rabbit | LD50 | oral | 182mg/kg (182mg/kg) | "Handbook of Analytical Toxicology," Sunshine, I., ed., Cleveland, OH, Chemical Rubber Co., 1969Vol. -, Pg. 33, 1969. | |
rat | LD50 | oral | 200mg/kg (200mg/kg) | Drugs in Japan Vol. 6, Pg. 252, 1982. |