MOLECULE

Piperidine

Piperidine, named after the genus Piper, which is Latin for pepper, has the molecular formula (CH2)5NH. It is a heterocyclic amine which consists of a six-membered ring containing five methylene units and one nitrogen atom. Piperidine is a strong basic compound. It is a colorless fuming liquid with an ammoniacal and pepper-like odor. It is found in black pepper fruit, oil and seed (Piper nigrum), barley seeds, celery plant, bell pepper and tobacco ( http://www.thegoodscentscompany.com/data/rw1009201.html#tooccur). Piperidine is also a constituent of cannabis smoke. It is volatilized during the combustion of cannabis (https://doi.org/10.1007/978-1-59259-947-9_2). In addition to cannabis plants (PMID: 6991645), piperidine was obtained from the plants Psilocaulon absimile (Aizoaceae) and in Petrosimonia monandra ( https://en.wikipedia.org/wiki/Piperidine#cite_note-17). Piperidine is metabolized by microbes and is potentially used as an anti-bacterial agent controlling bacterial populations within rhizomes (http//doi.org/10.1101/499731). Piperidine is a widely used building block and chemical reagent in the synthesis of organic compounds, including pharmaceuticals such as vasodilators and antipsychotic medications (PMID: 25255204). Piperidine is a widely used secondary amine and used to convert ketones to enamines. Enamines derived from piperidine can be used in the Stork enamine alkylation reaction. Piperidine is used as a solvent and as a base. The same is true for certain derivatives: N-formylpiperidine is a polar aprotic solvent with better hydrocarbon solubility than other amide solvents, and 2,2,6,6-tetramethylpiperidine is highly sterically hindered base, useful because of its low nucleophilicity and high solubility in organic solvents.