Piperidine

piperidinespiperidinylNC5H10pi'''pe'''ridinepiperdinepiperidinopiperidylpiperidynil
Piperidine is an organic compound with the molecular formula (CH 2 ) 5 NH.wikipedia
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Amine

aminoaminesamino group
This heterocyclic amine consists of a six-membered ring containing five methylene bridges (–CH 2 –) and one amine bridge (–NH–).
Examples of cyclic amines include the 3-membered ring aziridine and the six-membered ring piperidine.

Alkaloid

alkaloidspurine alkaloidalkaloid biosynthesis
Although piperidine is a common organic compound, it is best known as a representative structure element within many pharmaceuticals and alkaloids, such as natural-occurring solenopsins.

Anabasine

Other examples are the fire ant toxin solenopsin, the nicotine analog anabasine of tree tobacco (Nicotiana glauca), lobeline of Indian tobacco, and the toxic alkaloid coniine from poison hemlock, which was used to put Socrates to death.
Anabasine is a pyridine and piperidine alkaloid found in the Tree Tobacco (Nicotiana glauca) plant, a close relative of the common tobacco plant (Nicotiana tabacum).

Pyridine

pyridylpyridinesGattermann–Skita synthesis
Industrially, piperidine is produced by the hydrogenation of pyridine, usually over a molybdenum disulfide catalyst:
The suggestion by Körner and Dewar was later confirmed in an experiment where pyridine was reduced to piperidine with sodium in ethanol.

Fire ant

Solenopsisfire antsred ant
Other examples are the fire ant toxin solenopsin, the nicotine analog anabasine of tree tobacco (Nicotiana glauca), lobeline of Indian tobacco, and the toxic alkaloid coniine from poison hemlock, which was used to put Socrates to death.
Unlike many other ants, which bite and then spray acid on the wound, fire ants bite only to get a grip and then sting (from the abdomen) and inject a toxic alkaloid venom called solenopsin, a compound from the class of piperidines.

Heterocyclic compound

heterocyclicheterocycleheterocycles
This heterocyclic amine consists of a six-membered ring containing five methylene bridges (–CH 2 –) and one amine bridge (–NH–).

Piperine

5-(3,4-Methylenedioxyphenyl)-2,4-pentadienoyl-2-piperidine
Both men obtained piperidine by reacting piperine with nitric acid.

Conium maculatum

poison hemlockhemlockC. maculatum
Other examples are the fire ant toxin solenopsin, the nicotine analog anabasine of tree tobacco (Nicotiana glauca), lobeline of Indian tobacco, and the toxic alkaloid coniine from poison hemlock, which was used to put Socrates to death.
Conium contains the piperidine alkaloids coniine, N-methylconiine, conhydrine, pseudoconhydrine and gamma-coniceine (or g-coniceïne), which is the precursor of the other hemlock alkaloids.

Black pepper

pepperwhite pepperpeppercorn
The name comes from the genus name Piper, which is the Latin word for pepper.
Pepper contains phytochemicals, including amides, piperidines, pyrrolidines and trace amounts of safrole, which may be carcinogenic in laboratory rodents.

Piper (plant)

PiperpepperMacropiper
The name comes from the genus name Piper, which is the Latin word for pepper.
The piperidine functional group is named after the former, and piperazine (which is not found in ''P.

N-Formylpiperidine

N''-Formylpiperidine
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 a highly sterically hindered base, useful because of its low nucleophilicity and high solubility in organic solvents.
It is the amide of formic acid and piperidine.

Methylphenidate

RitalinConcertaMethylin
Methylphenidate is a central nervous system (CNS) stimulant of the phenethylamine and piperidine classes.

N-Chloropiperidine

N''-chloropiperidine
Upon treatment with calcium hypochlorite, piperidine convert to N-chloropiperidine, the chloramine with the formula C 5 H 10 NCl.
It is prepared by treatment of piperidine with calcium hypochlorite.

Lobeline

Other examples are the fire ant toxin solenopsin, the nicotine analog anabasine of tree tobacco (Nicotiana glauca), lobeline of Indian tobacco, and the toxic alkaloid coniine from poison hemlock, which was used to put Socrates to death.
A related alkaloid sedamine, with only one 2-phenylethyl group on the piperidine ring and found in plants of genus sedum, is known to be an inhibitor of pea seedlings amine oxidase, but its affinity to proteins such as the dopamine transporter has apparently not been tested.

Desoxypipradrol

Of these three piperidines, desoxypipradrol has the longest elimination half-life, as it is a highly lipophilic molecule lacking polar functional groups that are typically targeted by metabolic enzymes, giving it an extremely long duration of action when compared to most psychostimulants.

Thioridazine

Mellarilthioridazine hydrochloride
Thioridazine (Mellaril or Melleril) is a piperidine typical antipsychotic drug belonging to the phenothiazine drug group and was previously widely used in the treatment of schizophrenia and psychosis.

Nucleophile

nucleophilicnucleophilic attacknucleophilicity
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 a highly sterically hindered base, useful because of its low nucleophilicity and high solubility in organic solvents.
With E = −9.15 for the S-methyldibenzothiophenium ion, typical nucleophile values N (s) are 15.63 (0.64) for piperidine, 10.49 (0.68) for methoxide, and 5.20 (0.89) for water.

Mesoridazine

Serentil
Mesoridazine (Serentil) is a piperidine neuroleptic drug belonging to the class of drugs called phenothiazines, used in the treatment of schizophrenia.

Fluorenylmethyloxycarbonyl protecting group

Fmoc9-fluorenylmethoxycarbonyl
It may be cleaved by bases, typically a solution of piperidine:

Peptide synthesis

solid phase peptide synthesissynthetic peptidesolid-phase peptide synthesis
Fmoc deprotection utilizes a base, typically 20–50% piperidine in DMF.

Risperidone

RisperdalRisperdal (risperidone)
Risperidone contains the functional groups of benzisoxazole and piperidine as part of its molecular structure.

Dipipanone

Diconal
It closely resembles methadone, the only structural difference being the N,N-dimethyl moiety of methadone being replaced with a piperidine ring.

Phencyclidine

PCPangel dustphenylcyclidine
Piperidine is listed as a Table II precursor under the [[United Nations Convention Against Illicit Traffic in Narcotic Drugs and Psychotropic Substances]] due to its use (peaking in the 1970s) in the clandestine manufacture of PCP (1-(1-phenylcyclohexyl)piperidine, also known as angel dust, sherms, wet, etc.).
When smoked, some of the compound is broken down by heat into 1-phenylcyclohexene (PC) and piperidine.

United Nations Convention Against Illicit Traffic in Narcotic Drugs and Psychotropic Substances

19881988 UN Convention on Narcotics1988 UN Drug Convention
Piperidine is listed as a Table II precursor under the [[United Nations Convention Against Illicit Traffic in Narcotic Drugs and Psychotropic Substances]] due to its use (peaking in the 1970s) in the clandestine manufacture of PCP (1-(1-phenylcyclohexyl)piperidine, also known as angel dust, sherms, wet, etc.).