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#chemistry question: #coffee is an alkaloid. It's basic. Does anything interesting happens when I add lemon to my #tea? Does anything interesting happens when I add apple cider to my tea? What if I mixed coffeine with acetic anhydride? It turns morphine into heroine, what does it change coffeine into?
@licho serious question or idle musing?
@GetzlerChem just wondering
Heroin doesn't do anything at all except cross the Blood-Brain-Barrier faster than Morphine does. Then, enzymes in the brain remove the acetyl group to turn in back into Morphine. I don't know if if would work the same, but presumably treating caffeine with acetic anhydride could do something similar - you might get caffeine into your brain faster.
What if I mixed coffeine with acetic anhydride?
Coffeine cannot be acetylated, therefore there is no effect. No wait, your coffee will be tasting like vinegar.
@organic_chemistry thanks! Why can't it be acetylated? How do we usually know if things can or can't be acetylated?
I'm a dilettante in chemistry, thank you for patience ^^
@licho The molecule of interest need to have a "reactive handle". If you want to add a acetyl, which is called acetylation, you often need something like a free alcohol or amine. E.g. on morphine you have this group (often depicted in the upper left corner, the -OH). Although coffeine has some N atoms, all of them are already occupied and cannot be further substituted under standard conditions.
@organic_chemistry thank you! 
Alkaloid is a misnomer here then, isn't it? Coffeine isn't alkaline after all!
@licho The term alkaloid stands for a class of natural products, which may but not have to be alkaline. However, they always containing nitrogen.
@licho
Coffee (the prepared beverage) is an acid, not a base. It has a pH, on average, of 5. Did you mean to say caffeine? Is coffeine different from caffeine?
@Sup3rN0va yes, that's what I meant ^^ I meant coffee main alkaloid, caffeine. But it turns out it's also an acid XD