This video explains the structure, synthesis and metabolism of benztropine and amantadine
Oh the previous video we have seen the chemistry of some of the dopaminergic a a cone is like a bromocriptine so in this video i will be dealing with chemistry of the some more agents and deeper concerns and drugs like a chemistry of depends drop in as well as amantadine so let us first deal with the benz dropping so this is the structure of the benz atropine so
You can see it is having atropine during system and this trope entering system also having the diphenyl methane group and this when strokin also make promo krypton is usually available in combination with the with himself misson it that is meeting something else alfred the vents are open so then we get to benz atropine mesylate and this is a nomenclature of heat
When the dropping that is a three bends the hydral oxy tropane methane sulfonate so let us see it synthesis so it’s synthesis is a right from the knife in and meet him two phenyl groups which are linked by a medium grouper so this – and methane is first brominated by using roaming one of the hydrogen is replaced by a bromine so it’s like a free-radical substitution
Reactions of alkenes so one of the hydrogen is replaced with the bromine so we get to blow more derivative of diphenyl methane now this bromo derivative of diphenyl methane is treated with the drop in this is the structure of propane in the presence of sodium hydroxide then what happens the hydrogen from the top in alcoholic moiety and the bromine from the bloomwood
– And methane will be more this oxygen of droping will be linked to the within the carbon of the entire final meeting so thus we get big bends dropping in order to get the bends dropping in solid form will be treating with methane sulphonic acid so this sulphonic acid methane sulfonate part will be added hydrogen taken up by the nitrogen utilizing a lone pair of
Electrons present on the nitrogen hydrogen combine so nitrogen becomes quaternary so it is getting positive charge and the remaining negative addendum will be added to depends it repels so that’s we are getting final events at rope and missile eight coming to the metabolism of depends atropine these are the some of the possible metabolic pathways which are given
In a article so bends it drop and it will undergo both faysville reactions as well as face to biotransformation reactions so in a process 200 of s1 reaction it will undergo hydroxylation reaction so for prime group that is final groups will be given one frame to frame the and carbon of the final group will be given one prime does the para carbon will be getting the
Four prime position so the hydroxy group will be introduced at the para position of this benzene ring system a the best benzene ring system on earth are dis phenyl ring system so does we get for hydroxybenzene repair for prime hydroxyl benson trophy and similarly an oxidation also a kind of phase van reaction only so the nitrogen of the benz droplet will undergo an
Oxidation so it gives men the trophy and oxide and also another faysville reaction that is ending methylation as we see and this intro pending system is a and methyl group so this methyl group will be removed by a process called and demethylation so as a result of which we get and this methyl benzene so benz drop in an oxide four prime when the trophy for prime
Hydroxyl binds troponin and s metal bands dropping days are de metabolic products metabolites as a result of the phase bond reactions like an oxidation hydroxylation and demethylation reactions so once these metabolites are formed they will further undergo hydroxylation making the case of bands drop in and offset again our phenyl groups any one of these phenyl
Groups will be undergoing hydroxylation so we get four prime hydroxybenzoic an oxide and a noun or derivative also undergone that is under smith our bands and also under the reaction hydroxylation as a result of which we get em decimated for prime hydroxyl pence dropping okay so these are they a possible metabolic metabolic pathway for depends drop in drug coming
To the amounted in chemistry chemistry of a mine today so this is the structure of the amman today it is having another man tendering system with the primary of mine group and one of the analog of the amantadine is known as the material so the structural difference you can find here in the amount eternity is a primary amine hello but here in case of amantadine
The adamantium ring system and the nitrogen are linked by a car but with it it has groove here branch a little method so this a marketing is a dopamine facilitator so as i said earlier it is a primary a mine with a pk value of ten point eight it’s the center synthetic pathway so as i said it is where are the maintained their way to so the starting molecule will be
At an advantage and we can synthesize it from atom and this atom anton first will be brominated by using bromine so the one of the carbon of the ring carbon will be undergoing domination so we get bromide back then this brahmana again will be treated with methyl cyanide in the presence of sulfuric acid then this bromo will be replaced by acid i am i know grow so
We will be getting an acetyl imagining so now from this we can get a mountain by simply more of this acetyl group that is like a deep protection and so this hydrolysis of day ends and a chassis was h3 here so are mine hydrolysis will be performed by using sodium hydroxide so then amide hydrolysis takes place so that s it a group will be removed in the form of
Esta casa so there will be generation of primary amine group from this so that’s we get finally a marketing so does a marketing can be prepared from a demand death by brahma nation followed by treatment with metals in the presence of sulfuric acid then finally i might hydrolysis we can get imagining i’m into the metabolism so as mentally treasurer the classical
Literature that is textbooks the esper the information available in there it is excreted unchanged in the urine but one of the latest rk article is saying that this will be undergoing by a transformation reaction that is an escalation reaction because it is the only reactive side present in the structure of imagine remaining all our car carbohydrate chain only like
Adamantane chain only there is no reactive side here all except the amine functional primeira my primary amine functionality so be dutiful plans of this primary amine functional date with our logo and installation reaction to give america a romantic so this is the structure of and they stay a market so this is one of the possible metabolic pathway for they imagine
So this is this is as the less metabolism of imagine thank you
Transcribed from video
Chemistry of Benztropine & Amantadine By Dr N Swathi
