Caffeine Isomers and Their Effects on the Nervous System

[Delta2]

I noticed that different brands of espresso coffee have different effect on my nervous system. Some are really good in the sense that they wake me up and make me feel fresh and dynamic, while others do nothing, and others make me really jumpy and nervous and stressed.

Why is that? I am not good in chemistry but is it because the caffeine molecule has many types of isomers? (structural and or stereoisomers) and each caffeine isomer affect my nervous system in a different way?

 

[CWatters]

I think it's more likely some have far more caffeine than others.

 

[Borek]

No isomers of caffeine as far as I am aware.

(That is: there are other compounds that are isomers of caffeine, but they are no longer caffeine.)

 

[jim mcnamara]

You have the grade "A" answer there. - @CWatters answer.
https://www.caffeineinformer.com/caffeine-content/coffee-brewed - has a range of caffeine from 64mg -> 277mg per cup. See how coffee prep methods change the caffeine content.

 

[Delta2]

No isomers of caffeine as far as I am aware.

(That is: there are other compounds that are isomers of caffeine, but they are no longer caffeine.)

Er hm what do you mean by that, that the isomers of caffeine are synthesized in chemical labs and not found in nature coffee plants?

 

[Delta2]

You have the grade "A" answer there. - @CWatters answer.
https://www.caffeineinformer.com/caffeine-content/coffee-brewed - has a range of caffeine from 64mg -> 277mg per cup. See how coffee prep methods change the caffeine content.

I could never imagine there could be such a big variation in caffeine density depending on brand and how it is prepared..Up to 4x..or even more.

 

[jim mcnamara]

https://www.ncbi.nlm.nih.gov/pubmed/17514358 there are many xanthine compounds in plants. For example, mate (Holly plant in South America), tea (theine), and chocolate all contain caffiene and other xanthine relatives. Xanthines have a lot of biomedical effects - the xanthines in ordinary tea are bronchodilators.

 

[Borek]

Er hm what do you mean by that, that the isomers of caffeine are synthesized in chemical labs and not found in nature coffee plants?

OK, too many shortcuts and hand waving in one post.

There are many types of isomers. Sometimes the molecule has the same overall formula, but is different structurally (structural isomers, often thousands of such, they are considered to be different compounds). Sometimes the molecule is very similar (same overall formula, almost identical structure), but differs only by subtle geometry (like stereoisomers). There are no stereoisomers of caffeine, there are plenty of structural isomers. Differences of a kind you have described are common for a stereoisometry.

 

[CWatters]

I only drink decafinated coffee and even that has some caffeine in it. With some brands it feels like they have hardly taken any out.

 

[Delta2]

I only drink decafinated coffee and even that has some caffeine in it. With some brands it feels like they have hardly taken any out.

What other chemical compounds coffee has (except caffeine) that are useful for a human organism?

Something else I want to ask (don't laugh), I noticed coffee also acts as a sort of mild laxative (it helps me when I am constipated), is it caffeine to blame also for this laxative effect?

 

[Borek]

Something else I want to ask (don't laugh), I noticed coffee also acts as a sort of mild laxative (it helps me when I am constipated), is it caffeine to blame also for this laxative effect?

Quite normal, to quote wikipedia: Coffee and caffeine can affect gastrointestinal motility.

Caffeine is also mildly diuretic, although we easily develop tolerance.