Mood enhancement trivia...

[helen99]

I just received the Thinkgeek catalog, which has a line of teeshirts with caffeine molecules printed on them (I have one). Recently they've added a chocolate molecule to their line of shirts. The two molecules looked so much alike that at first I thought they were identical. There is a difference, though. The first image is caffeine, and the second one is chocolate.

Comments

[brigidsblest.livejournal.com]

They're...what, one molecule apart? H3C instead of H? (I never took chemistry. I have no idea what either of those are. Is H Hydrogen? It can't be Helium.)

[hummingwolf.livejournal.com]

Not one molecule apart--each of those two diagrams is of a molecule. I forget the name for those individual units (my encyclopedia-fu is not strong this evening), so here's hoping one of the resident science geeks will show up and tell us soon. :-)

(H is hydrogen, yes. If you're interested, the other elements found in those molecules are carbon, oxygen, and nitrogen.)

[shaharazad.livejournal.com]

The unit is a methyl group, basically a carbon atom bonded to the molecule with a hydrogen bonded to each of its three remaining bonding locations.

[mmsword.livejournal.com]

Darn me for getting distracted with the process of synthesis of theobromine. You win this round!

[mmsword.livejournal.com]

That would be a "group" in the context of organic chemistry. The difference between Caffeine and Theobromine being one methyl group.
...
Science!

[helen99.livejournal.com]

This might be a place to start.. Their intent was to synthesize caffeine, but one of the steps seems to be enzymatically producing theobromine from tea leaves by adding insoluble polyvinylpyrrolidine. The question becomes, where does one find insoluble polyvinylpyrrolidine. I don't remember seeing that at my local brew shop.

[brigidsblest.livejournal.com]

Not atom. Unit?

[helen99.livejournal.com]

I think the unit they're talking about is the CH3 methyl group, composed of 4 atoms.

[dogemperor.livejournal.com]

Specifically, caffeine is methylated theobromine (if the chemical structure above is accurate); one of the hydrogen atoms in the theobromine molecule is replaced by a methyl group (the H₃C, qhich is a pretty common "molecule acting as atom" in organic chemistry).

There's a lot of this sort of thing in organic chemistry, and methylating a molecule can change its effects somewhat (methanol versus ethanol, for instance); more commonly, the two molecules act almost but not *precisely* the same (in a less innocuous context than theobromine and caffeine, much the same goes on with amphetamine and methamphetamine--and with a *lot* of different opioid pharmaceuticals).

[helen99.livejournal.com]

I remember taking Organic Chemistry in college, and totally loving the subject. I've forgotten most of it, but it was the most fun I've had in a course (that and regular chemistry plus lab). I actually made up a filk to the tune of "Tannenbaum" that goes,

"Oh Isovaleraldehyde, how lengthy are thy carbons,
Oh Isovaleraldehyde, how lengthy are thy carbons,
five carbons long, five carbons wide,
no matter how we tried and tried
We could not reach the other side
of Isovaleraldehyde..."

Ah, the fond memories.

Yes, I'm a little strange...

[historychick49.livejournal.com]

Wow. I had no idea chocolate and caffeine were so similar molecularly.

[helen99.livejournal.com]

I didn't know that either. My guess is that coffee would harm a dog the same way chocolate does. I think a lot of people who can't drink coffee also can't eat chocolate.

[historychick49.livejournal.com]

True! One of my friends at college was allergic to caffeine. No coffee/tea/soda/whatever, and no chocolate either. She couldn't even have more than one or two squares of Hershey's chocolate before it started affecting her.

[helen99.livejournal.com]

Chemically, she would be my polar opposite... Very strong, fresh-ground coffee is one of my major food groups... Chocolate is not a major food group but when I do eat it, I use the medicinal variety...

This and This

[hummingwolf.livejournal.com]

Technically, that molecule isn't "chocolate," but theobromine, an alkaloid found in chocolate. Theobromine is also found in small amounts in the kola nut and tea plant (oh, and Wikipedia tells me it's in guarana berry too).</nitpick>

Mmm... chocolate.

[helen99.livejournal.com]

Right - Off-the-shelf chocolate would be far more complex and consist of many molecules (sugars, fats, etc.). Interesting that Guarana has it - I actually like to drink guarana tea.

[dogemperor.livejournal.com]

So technically caffeine is methyltheobromine? Nifty :D (And it does explain why they have similar, if not identical, effects.)

(And yes, Wikipedia does at least seem to confirm the chemical structure of caffeine as methyltheobromine, of a sort; caffeine article notes specifically that most plants that naturally contain caffeine also contain the related xanthine alkaloids theobromine (which not only is the stuff that makes chocolate Happy Stuff but is also a mild bronchodilator--you can give it to rats with respiratory problems, and I've found if I'm feeling particularly bronchial-cruddy some 90-100 percent cacao stuff does quite the trick to clear my chest out) and theophylline (which is typically used for asthma and is much stronger than either caffeine or theobromine).

[helen99.livejournal.com]

I just found a couple of scientific studies about the anti-tussive effects. For some reason, even though I usually don't eat candy, I always have my 87% Dagoba... It always felt more like food than candy.

[sheekayt.livejournal.com]

There is a distinctive difference between chocolate and candy. I only very rarely eat chocolate flavored candy (usually when I'm low-blood-sugar desperate and it's the only thing on hand)

[helen99.livejournal.com]

I had a little bit of "chocolate" candy on Friday (someone brought in a big brick of what amounted to dove-bar-like substance). It was pretty gross...

This is da stuff: Chocosphere...
Noir Infini 99%
Dagoba 87%

[toxicelement.livejournal.com]

Is it sad that I saw this and thought, "okay, so that one's caffeine, and that one is... wait, what IS that? hrm" -- though I guess, it'd be pretty bad if i didnt recognize the caffeine off the bat. I'm not sure if having it tattooed upon my person makes this better or worse. haha

[helen99.livejournal.com]

Probably better, especially if they used caffeinated ink...