you can’t “neutralize” capsaicin. the best you can do is apply something that can carry it away, and being capsaicin is as you said lipophilic, something fatty might help. Vinegar and alcohol seem like they’d just augment one burning sensation with another.
of course, even if you eat/drink something which lessens the burn in your mouth, you’re still going to pay for it the next day when the spicy food you ate decides to make its exit.
Honey. It coats your tongue, protecting your taste buds from the capsaicin. It also dulls the heat by overloading your senses with sweet. I’ve not tested it personally (I don’t intentionally eat spicy food), but I’ve seen others use it with positive results.
The molecule has several reactive functional groups. Turning it into something else might count as neutralizing. However, I do not know that it is reactive under any conditions that are friendly for the human mouth.
Does anyone know how it is metabolized in the body? If it is metabolized in the body? Many of us know very well that metabolism, if it occurs, can be incomplete.
If it’s bad enough that you really need to neutralize the burn in your mouth–a napkin. It’s a bit gross, and obviously only works in areas you can reach to scrub, but a paper napkin will get a lot of the stuff off fast. (The idea behind the sugar suggestion might be similar–scouring the affected surfaces with the granular sugar.) Following it up with milk or yogurt should help with the rest, but you probably need to swish it around in your mouth a bit before swallowing to do any good.
All that’s assuming you don’t mean taking something to neutralize it farther downstream. I think you’re out of luck there. Read the warning labels.
There was a hot sauce specialty store in my general regional vicinity that would offer small sized tootsie rolls for relief from a sauce sample that was too hot. Anecdotal all the way, I’ve never tried it.
Look to the spicy cuisines. Spicy Mexican food is accompanied by lots of fatty cheeses, sour cream, etc, to dilute the capsaicin, and tequila to dissolve it with.
While capsaicin is most often referred to as “fat soluble”, what it more technically is is a nonpolar molecule. Nonpolar molecules are soluble in other nonpolar molecules, like oil, and not nearly so soluble in polar molecules, like water. Alcohol has a polar and nonpolar end, so it will act as a solvent for both polar and nonpolar molecules.
So alcohol will do it, the stronger the alcohol (and therefore the less polar water), the better. Of course, too strong and you can’t keep it in your mouth without replacing one burn with another. So…stronger than beer, less strong than Everclear. Think…oh, tequila. Or strong margaritas.
Or you can take a mouthful of olive or coconut oils and swish for a few minutes and spit it out. It’s called “oil pulling,” and it’s all the rage in oral health these days.
Real answer: You want to go with something handy that you’d find in a Mexican restaurant so you don’t embarrass yourself. Sour cream works well, but you’ll get embarrassed anyway if you grab a chipful off your date’s entree.