| Identification | More | [Name]
Chloropyramine hydrochloride | [CAS]
6170-42-9 | [Synonyms]
CHLOROPYRAMINE HCL
CHLOROPYRAMINE HYDROCHLORIDE
CHLOROPYRAMINE MONOHYDROCHLORIDE
N-P-CHLOROBENZYL-N,N-DIMETHYL-N-(2-PYRIDYL)ETHYLENEDIAMINE HYDROCHLORIDE
N-P-CHLOROBENZYL-N',N'-DIMETHYL-N-[2-PYRIDYL]ETHYLENEDIAMINE HYDROCHLORIDE
N-P-CHLOROBENZYL-N',N'-DIMETHYL-N-[2-PYRIDYL]LETHYLENEDIAMINE HYDROCHLORIDE
Chloropyramine HCI
N-[(4-chlorophenyl)methyl]-N’,N’-dimethyl-N-2-pyridinyl-1,2-ethanediamine | [EINECS(EC#)]
228-216-2 | [Molecular Formula]
C16H21Cl2N3 | [MDL Number]
MFCD00079009 | [Molecular Weight]
326.26 | [MOL File]
6170-42-9.mol |
| Chemical Properties | Back Directory | [Melting point ]
172-174° | [storage temp. ]
Inert atmosphere,Room Temperature | [solubility ]
Chloroform (Slightly), Methanol (Slightly), Water (Slightly) | [form ]
neat | [color ]
White to Off-White | [Major Application]
forensics and toxicology
pharmaceutical (small molecule)
veterinary | [InChI]
1S/C16H20ClN3.ClH/c1-19(2)11-12-20(16-5-3-4-10-18-16)13-14-6-8-15(17)9-7-14;/h3-10H,11-13H2,1-2H3;1H | [InChIKey]
VEYWWAGBHABATA-UHFFFAOYSA-N | [SMILES]
Cl.CN(C)CCN(Cc1ccc(Cl)cc1)c2ccccn2 | [CAS DataBase Reference]
6170-42-9(CAS DataBase Reference) |
| Hazard Information | Back Directory | [Originator]
Chloropyramine,Vramed | [Uses]
Chloropyramine hydrochloride is a neurotransmitter related agent for research of drug analysis. Also, it is designed to disrupt the focal adhesion kinase (FAK) and vascular endothelial growth factor receptor-3 (VEGFR-3) interaction in neuroblastoma. | [Uses]
synthetic | [Manufacturing Process]
A solution comprising 40 parts of 2-bromopyridine, 100 parts of N,N-dimethylN'-(4-chlorobenzyl)ethylenediamine and 100 parts of quinoline is heated at
140-145°C for 5 hours. The oil layer after washing with 30% sodium
hydroxide solution is distilled, and the fraction which distills at 142-170°C/1
mm is collected. This oil is converted to the monohydrochloride and
recrystallized from a mixture of amyl alcohol and ether. The
monohydrochloride salt of N,N-dimethyl-N'-(4-chlorobenzyl)-N'-(2-pyridyl)
ethylenediamine is obtained which melts at 167-168.4°C.
N,N-Dimethyl-N'-(4-chlorobenzyl)-N'-(2-pyridyl)ethylenediamine may be
prepared by another method:
To a mixture of 100 ml of liquid ammonia and about 80 mg of black iron oxide
was added 0.78 g (0.02 atom) of potassium. When all of the potassium had
reacted, 3.3 g of N,N-dimethyl-N'-(2-pyridyl)ethylenediamine was added. After
the addition of 75 ml of dry toluene the ammonia was removed on the steam
bath. To the cooled and stirred mixture was added 4.26 g of p-chlorobenzyl
chloride, and the reaction mixture was stirred on the steam bath for 11 hours.
It was then filtered and concentrated to an oil. This concentrate was taken up
in ether, and the ethereal solution was washed with water, dried over sodium
sulfate, and concentrated. Distillation gave 2.96 g of yellow liquid. Treatment
of this distillate with an equivalent quantity of hydrogen chloride in absolute
alcohol and precipitation by the addition of anhydrous ether gave 2.33 g of
the N,N-dimethyl-N'-(4-chlorobenzyl)-N'-(2-pyridyl)ethylenediamine
hydrochloride. | [Therapeutic Function]
Antihistaminic | [in vivo]
Chloropyramine hydrochloride causes a dramatic reduction of tumor growth in both model systems whereby the tumor size in the treated groups is approximately 20% of the tumor size in vehicle control groups. Doxorubicin administered at 3 mg/kg causes approximately 60% reduction of tumor growth, but has no effect on tumor growth at 0, 3 mg/kg. In contrast, there is a modest effect of Chloropyramine hydrochloride alone (50% reduction of tumor growth). The low-dose combination of Chloropyramine hydrochloride and doxorubicin has a prolonged anti-tumor effect (85% reduction of tumor growth) that is greater than either drug alone[1]. | [IC 50]
H1 Receptor; VEGFR-3 |
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