21730-16-5 Usage
Description
Metapramine, also known by its brand name TIMAXEL, is a tricyclic antidepressant belonging to the dibenzoazepine class. It exhibits a pharmacological profile akin to other tricyclic antidepressants and demonstrates a rapid clinical onset of action. Metapramine is distinguished from other tricyclics by its significant enhancement of norepinephrine turnover and minimal inhibition of its reuptake. However, it shares the common characteristic of downregulating β-receptors with the tricyclic class.
Uses
Used in Pharmaceutical Industry:
Metapramine is used as a norepinephrine reuptake inhibitor for the treatment of depression. Its primary application is to increase the levels of norepinephrine in the brain, which contributes to an improvement in mood and alleviation of depressive symptoms. As a tricyclic antidepressant, Metapramine is particularly effective for patients experiencing major depressive disorder or other mood disorders where norepinephrine levels are implicated.
Additionally, due to its minimal impact on serotonin and dopamine reuptake, Metapramine may be a suitable option for patients who require selective norepinephrine reuptake inhibition without significant interference with other neurotransmitters, potentially reducing the risk of side effects associated with broader reuptake inhibition.
Originator
Rhone-Poulenc (France)
Manufacturing Process
5-Methyl-dibenzo[b,f]azepine (4.1 g), N-diethylaminoborane (1.7 g) and freshly distilled toluene (150 cc) are introduced into a 500 cc three-neck flask equipped with a dropping funnel and a condenser, and protected against moisture by a calcium chloride guard tube. The solution is heated under reflux (110°C) for 22 hours under a nitrogen atmosphere and then cooled. A 2 N aqueous sodium hydroxide solution (33 cc) is then run in followed by an 0.316 N aqueous methylchloramine solution (190 cc), the addition of which takes 9 minutes. The mixture is stirred for 1 hour and then decanted. The organic layer is washed with water until it has a pH of 6 and is then extracted with 2 N hydrochloric acid (5 times 50 cc), dried over sodium sulfate, filtered and evaporated. Recrystallization of the residue from petroleum ether yields some unconverted 5-methyl-dibenzo[b,f]azepine (2.17 g). The aqueous acid solution is rendered alkaline by adding 2 N sodium hydroxide solution. After extracting with diethyl ether (3 times 100 cc), drying the extracts over potassium carbonate, treating them with decolorizing charcoal, filtering and evaporating the ether, a yellowish oil (0.9 g), identified as 5-methyl-10-methylamino-10,11-dihydrodibenzo[b,f]azepine, is obtained in
a yield of 37.5%.
Methylchloramine can be prepared by adding an aqueous solution of sodium
hypochlorite to an aqueous solution of methylamine in accordance with the
process described by W.S. Metcalf, J. Chem. Soc.1942,148.
Therapeutic Function
Antidepressant
Check Digit Verification of cas no
The CAS Registry Mumber 21730-16-5 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,1,7,3 and 0 respectively; the second part has 2 digits, 1 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 21730-16:
(7*2)+(6*1)+(5*7)+(4*3)+(3*0)+(2*1)+(1*6)=75
75 % 10 = 5
So 21730-16-5 is a valid CAS Registry Number.
InChI:InChI=1/C16H18N2/c1-17-14-11-12-7-3-5-9-15(12)18(2)16-10-6-4-8-13(14)16/h3-10,14,17H,11H2,1-2H3
