Anyone recognize this molecule?

This is 8-methyl-N-vanillyl-6-nonenamide, an alkaloid which is hydrophobic, colorless, odorless, and is a crystalline to waxy compound.
Of course you know what this is! All chileheads do, right? This is the formula & structure for our beloved capsaicin. I’ve been doing quite a bit of research about capsaicin concerning a research project for my residency in anesthesiology, so here’s an excerpt from an article written by Mick Vann from the Austin Chronicle back in 2002 which discusses some of the finer points of this subject:
Chemists found that a chile’s heat is created by a combination of seven closely related organic compounds called capsaicinoids, which are found in no other plant. Although all seven capsaicinoids generate heat, that madcap duo capsaicin and dihydrocapsaicin are the most prevalent, with capsaicin being the most macho by far. The compounds are produced by microscopic glands on the placenta, or vein, along the chile’s inner wall. This explains why one can lower the pungency of a chile by removing the ribs and seeds, because it is this area that holds the mother lode of capsaicin.
Pure capsaicin is a dark red, solid, odorless organic compound that when crystallized, forms long, hexagonal, needle-like, evil-looking crystals. From an elemental point of view, capsaicin is known as 8-Methyl-N-vanillyn-6-nonenamide, and yes, vanilla is a first cousin of capsaicin, which might seem strange from a taste point of view.
It’s insoluble in water, so no matter how much water you drink to try to quell the heat, it will only bloat you and make you pee. Capsaicin is soluble in vegetable and mineral oils, meaning that the most effective way to cool the burn is with dairy fat, such as that found in milk, yogurt, and ice cream. You could also drink oil or eat lard, but you might want to reserve that for only the most extreme situations. It is also soluble in ethyl alcohol, making Everclear an effective (but highly impractical) means of cooling down those taste buds. Beer’s ethyl alcohol concentration is too low to be very effective, so once again we’re back to the bloating and peeing part while the mouth still burns.
Capsaicin melts at 149 degrees F, which means that a warm dish containing chile will permeate and coat the mouth much faster than, say, a bowl of cold salsa. It is a surprisingly stable compound, unaffected by heat or cold, and keeps its potency whether it’s frozen, cooked, or desiccated. It is one of the most pungent compounds known to man, capable of detection by the human tongue in dilutions of one part per 17 million! A single milligram of pure capsaicin (the equivalent of about 10 grains of salt) placed on the palm of an ungloved hand would feel like a burning spike and would blister the skin.
Human nerve cells have receptor proteins for binding with capsaicin. When we eat chile and these receptors are stimulated, they carry a signal from the tongue to the spinal cord and then to the brain. It is then when we realize that we have eaten something spicy. At the same time, receptors in the brain are stimulated to release endorphins, which are natural painkillers we synthesize, promoting a sense of elation and well-being. Luckily, at the same time, capsaicin causes a long-term desensitization to the pain of the heat. Repeated stimulation of these sensory nerves produces a reduced response curve due to an influx of calcium ions entering the nerve, which can actually kill nerve endings over time. This is a very similar response to that of the addiction of drugs. In summation, we eat chile we burn we feel elated and want to eat more we eat more and become desensitized we are addicted and elated!
A 1980 study proved we are in little danger from “normal” consumption. It determined an average-sized person would have to chug a half gallon of Tabasco sauce in a short period of time to overdose and become unconscious (a warning perhaps to all of the frat houses out there). Not to worry though, because capsaicin alkaloids are quickly metabolized and excreted out of the body in one’s urine within a few hours after consumption.
A half-gallon of Tabasco sauce? I can think of a far better way to consume my capsaicin, and not in amounts to make me overdose or become unconscious. (BTW…check out the Wikipedia entry on capsaicin. It’s pretty interesting.)
Hot sauce, anyone? Sounds good to me.




















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