Molecules: You'd better learn to live with them.
Piperidine is a useful little heterocycle - Walter Gilbert won a Nobel Prize, due in part to his development of a method of sequencing DNA (which uses piperidine as a base). It also has some use in peptide synthesis. Piperidine is also a very useful thing to hang off a drug, because it adds some lipophilic bits (the ring is mostly paraffinic carbon, after all), as well as an amine. These are often two very useful things to have in a drug molecule.
There are also some less-savory uses of piperidine.
Piperidine derivatives are found in fire ant venom. It is also a precursor to PCP and has been a controlled substance for some time because of this use.
One last thing - some perfumists and chemists claim that piperidine smells like pepper. I don't think so. It smells noxious and musty, like all low-molecular amines to my nose. Maybe perfumery boffins can get it to make me think "pepper" in the right combination with other aromas, but out of the bottle, it just smells rank. It is, however, a substituent of the piperine molecule - the main aroma compound in black pepper. I suspect these names all come from the genus, Piper, to which black pepper belongs.
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Comments
I agree with you completely on the smell of piperidine. It's definitely not peppery. It kind of reminds me of the spermine or spermidine (can't remember which) that was in the back of the hood next to the cadaverine.
Posted by: MiddleO'Nowhere | January 26, 2007 9:46 AM
I also read that you can use 4-methyl piperidine in peptide chemistry. Saves you all the paperwork ...
Posted by: Wim | January 26, 2007 10:23 AM
Posted by: sparc | January 26, 2007 10:36 AM
Piperidine smells positively wonderful compared to any given isonitrile (R-NC). Incredibly useful molecules (Ugi, Passerini, and Grobke reactions), but they have been limited by their incredibly vile smell (t-butyl isonitrile is a representative one as far as smell goes).
A recent JACS article talked about combining an isonitrile and an ester in the same molecule (generally, the ester functional group won and the compounds smelled somewhat nice).
Isonitriles smell as vile as mercaptans, but they have an awful, lingering boquet that is all their own. :)
Posted by: BlazingDragon | January 29, 2007 7:24 PM
Oh, to us here generically amine-y, not peppery. And always a source of complaints when I refill the peptide synthesizers, for a little tiny bit goes a long way as far as bad smell goes.
Posted by: Michael Pereckas | July 24, 2007 6:15 PM
its funny middle o nowhere, you should say cadaverine aka
diaminopentane. Heating the di-hydrochloride of di-aminopentane produces piperidine hydrochloride and amonium
chloride aka sal amoniac. cyclized cadverine basicly
cadaverine comes from decarboxylation of lysine by decomposition of thigs that contain the amino acid lysine.
cadaverine is called that exactly cadaver because it is
present in dead people, but also other dead stuff. pretty
neat hu
Posted by: william | September 29, 2007 9:35 PM