| Identification | Back Directory | [Name]
10-[(1-methyl-3-piperidyl)methyl]-10H-phenothiazine monohydrochloride | [CAS]
2975-36-2 | [Synonyms]
Mepazine hydrochloride
10-((1-methylpiperidin-3-yl)methyl)-10H-phenothiazine hydrochloride
10-[(1-methyl-3-piperidyl)methyl]-10H-phenothiazine monohydrochloride
10H-Phenothiazine, 10-[(1-methyl-3-piperidinyl)methyl]-,monohydrochloride | [EINECS(EC#)]
221-020-8 | [Molecular Formula]
C19H23ClN2S | [MOL File]
2975-36-2.mol | [Molecular Weight]
346.917 |
| Chemical Properties | Back Directory | [Melting point ]
180-181 °C | [Boiling point ]
180-183 °C(Press: 0.5 Torr) | [storage temp. ]
Store at -20°C | [solubility ]
DMSO: 50 mg/mL (144.13 mM) | [form ]
Solid | [color ]
White to off-white | [Water Solubility ]
H2O: 2.5mg/mL
DMSO: 25mg/mL | [InChI]
1S/C19H22N2S.Cl/c1-20-12-6-7-15(13-20)14-21-16-8-2-4-10-18(16)22-19-11-5-3-9-17(19)21;/h2-5,8-11,15H,6-7,12-14H2,1H3; | [InChIKey]
ZGQUIYCUOPQIDJ-UHFFFAOYSA-N |
| Hazard Information | Back Directory | [Originator]
Pacatal,Warner Lambert,US,1957 | [Uses]
Mepazine hydrochloride is a cell-permeable phenothiazine derivative that inhibits mucosa-associated lymphoid tis 1(MALT1). It does not inhibit the caspase 3 or 8 proteolytic activity in a reversible and non-competitive manner. It blocks anti-CD3/CD28-stimulated IL-6 production in primary murine CD4+ T-cell and human peripheral blood mononuclear cell (PBMC) cultures. Mepazine has been observed to inhibit the MALT1 activity in activated B cell-like diffuse large B cell lymphoma (ABC-DLBCL)and RelB cleavage, resulting in effective blockage of nuclear factor (NF-κB)-dependent interleukin-6, 10 as well as anti-apoptoticB-cell lymphoma - extra-large (Bcl-xL) and FLIP-L expression. Mepazineshows ABC-DLBCL-selective cytotoxicity over GCB-DLBCL both in cultures in vitro and in mice in vivo. | [Manufacturing Process]
A 500 cc flask equipped with a mechanical stirrer, reflux condenser and a soda-lime tube was filled with 230 cc of absolute xylene, 27.5 g of 1-methyl3-bromomethylpiperidine, 53.3 g of phenothiazine and 14.2 g of finely powdered sodium amide, and the solution was heated under reflux for 6 hours. After cooling water was added and the batch was extracted with ether. As the hydrochloric acid salt of the obtained phenothiazine derivative is difficultly soluble in water, the further processing was carried out by way of the acetate. The etheric solution was extracted several times in a separating funnel with dilute acetic acid. The combined aqueous extracts were basified, extracted with ether, dried with potassium carbonate and, after removal of the ether, distilled in vacuo.
Yield = 64%; boiling point 230°C to 235°C at 4 mm; melting point of
hydrochloride is 180°C to 181°C. | [Therapeutic Function]
Tranquilizer | [Biological Activity]
Cell permeable: yes''Primary Target
MALT1 |
|
|