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Mclobemide Research Paper

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Moclobemide (4-chloro-N-(2-morpholinoethyl)benzamide) is an antidepressant, which is not currently licensed for use in the United States. The compound was originally tested as a lipid-lowering drug, but scientists later determined that it had a greater effect on inhibiting the enzyme monoamine oxidase (MAO). MAO’s are important for brain function, as their primary function is to degrade or “break down” the hormones serotonin, dopamine, and noradrenaline. Moclobemide is considered an MAO inhibitor, or MAOI. MAOIs block the ability of MAOs to degrade these “feel-good” hormones. Once these enzymes are blocked, the concentrations of serotonin, dopamine, and noradrenaline increase and the drugs have an antidepressant effect.1 There is, however, …show more content…

4-(2-aminoethyl)morpholine (742 mg, 5.7 mmol) and acetone (10 mL) were mixed together on ice, while a mixture of 4-chlorobenzoyl chloride (0.55 ml, 4.3 mmol) in acetone (2.5 mL) was added drop-wise for 10 minutes. Then, the mixture was mixed on ice for an addition five minutes, then for ten minutes at room temperature. Diethyl ether (10 mL) was added to the mixture and the resultant white precipitate was filtered. The product was recrystallized using ethanol (95%) and filtered. After drying, the crystals were dissolved in a mixture of dichloromethane (10 mL) and ammonia (concentrated, 10 mL). The organic layer was removed and the aqueous layer was washed with dichloromethane (10 mL). The combined organic layer was dried with sodium sulfate (anhydrous) and evaporated, which afforded a white powder (0.68 g, 66%) mp: 130-133°C; 1H NMR (400 MHz, CDCl3) δ (ppm) 7.71 (d, 2H), 7.41 (d, 2H), 6.87 (s, 1H), 3.73 (t, 4H), 3.53 (q, 2H), 2.60 (t, 2H), 2.5 (t, 4H); IR (ATR) υmax (cm-1) 3277, ~2900, 1633, 1595, 1546, 1486, 1469, 1461, 1142, 1116, …show more content…

The signal at 6.87 ppm in the 400 MHz 1H NMR is the strongest support for a pure product. This singlet peak, integrated at one, is indicative of the singular proton attached to the nitrogen in the product Moclobemide. If the starting material 4-(2-aminoethyl)morpholine were present, there would be different singlet peak with an integral value of 2. However, there is no other singlet peak, indicating that the product is free of reactant contamination. All of the other peaks found on the 1H NMR spectrum are similar to peaks one would find in an NMR spectrum of the starting products. The doublet peaks at 7.72 ppm and 7.41 ppm with integral values of two are representative of the protons on the benzene ring. The triplet peak at 3.74 ppm with an integral value of 4 is indicative of the four protons surrounding the oxygen in the ring structure while the triplet peak at 2.51 ppm with an integral value of 4 is conclusive of the protons surrounding the nitrogen in the ring structure. Finally, the two triplets with integral values of 2, found at both 3.53 and 2.60 ppm are representative of the protons found between the amide group and the nitrogen-oxygen ring structure in Moclobemide. The only peak that confirms that this is the spectrum of Moclobemide and not a starting material is that singular peak found at 6.87

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