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Piperidine information


Piperidine[1]
Names
IUPAC name
Piperidine
Preferred IUPAC name
Piperidine[2]
Other names
Hexahydropyridine
Azacyclohexane
Pentamethyleneamine
Azinane
Identifiers
CAS Number
  • 110-89-4 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:18049 checkY
ChEMBL
  • ChEMBL15487 checkY
ChemSpider
  • 7791 checkY
ECHA InfoCard 100.003.467 Edit this at Wikidata
EC Number
  • 203-813-0
IUPHAR/BPS
  • 5477
KEGG
  • C01746
PubChem CID
  • 8082
RTECS number
  • TM3500000
UNII
  • 67I85E138Y checkY
UN number 2401
CompTox Dashboard (EPA)
  • DTXSID6021165 Edit this at Wikidata
InChI
  • InChI=1S/C5H11N/c1-2-4-6-5-3-1/h6H,1-5H2 checkY
    Key: NQRYJNQNLNOLGT-UHFFFAOYSA-N checkY
  • InChI=1/C5H11N/c1-2-4-6-5-3-1/h6H,1-5H2
  • InChI=1/C5H11N/c1-2-4-6-5-3-1/h6H,1-5H2
    Key: NQRYJNQNLNOLGT-UHFFFAOYAY
SMILES
  • C1CCNCC1
Properties
Chemical formula
C5H11N
Molar mass 85.150 g·mol−1
Appearance Colorless liquid
Odor Semen-like,[3] fishy-ammoniacal, pungent
Density 0.862 g/mL
Melting point −7 °C (19 °F; 266 K)
Boiling point 106 °C (223 °F; 379 K)
Solubility in water
Miscible
Acidity (pKa) 11.22 (protonated)[4]
Magnetic susceptibility (χ)
-64.2·10−6 cm3/mol
Viscosity 1.573 cP at 25 °C
Hazards
GHS labelling:
Pictograms
GHS02: FlammableGHS05: CorrosiveGHS06: Toxic
Signal word
Danger
Hazard statements
H225, H311, H314, H331
Precautionary statements
P210, P233, P240, P241, P242, P243, P260, P261, P264, P271, P280, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P310, P311, P312, P321, P322, P361, P363, P370+P378, P403+P233, P403+P235, P405, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasolineInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
3
3
0
Safety data sheet (SDS) MSDS1
Legal status
  • BR: Class D1 (Drug precursors)[5]
Related compounds
Related compounds
Pyridine
Pyrrolidine
Piperazine
Phosphorinane
Arsinane
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Piperidine is an organic compound with the molecular formula (CH2)5NH. This heterocyclic amine consists of a six-membered ring containing five methylene bridges (–CH2–) and one amine bridge (–NH–). It is a colorless liquid with an odor described as objectionable, typical of amines.[6] The name comes from the genus name Piper, which is the Latin word for pepper.[7] 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.[8]

  1. ^ "International Chemical Safety Card 0317".
  2. ^ "Front Matter". Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 142. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.
  3. ^ Amoore, J. E. (1975). "Specific anosmia to 1-pyrroline: The spermous primary odor". J. Chem. Ecol. 1 (3): 299–310. Bibcode:1975JCEco...1..299A. doi:10.1007/BF00988831. S2CID 19318345.
  4. ^ Hall, H. K. (1957). "Correlation of the Base Strengths of Amines". J. Am. Chem. Soc. 79 (20): 5441–5444. doi:10.1021/ja01577a030.
  5. ^ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-15.
  6. ^ Frank Johnson Welcher (1947). Organic Analytical Reagents. D. Van Nostrand. p. 149.
  7. ^ Senning, Alexander (2006). Elsevier's Dictionary of Chemoetymology. Amsterdam: Elsevier. ISBN 978-0-444-52239-9.
  8. ^ Pianaro, Adriana; Fox, Eduardo G.P.; Bueno, Odair C.; Marsaioli, Anita J. (May 2012). "Rapid configuration analysis of the solenopsins". Tetrahedron: Asymmetry. 23 (9): 635–642. doi:10.1016/j.tetasy.2012.05.005.

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Piperidine

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Piperidine is an organic compound with the molecular formula (CH2)5NH. This heterocyclic amine consists of a six-membered ring containing five methylene...

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Piperine

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Piperine has been synthesized by the action of piperonoyl chloride on piperidine. Piperine forms salts only with strong acids. The platinichloride B4·H2PtCl6...

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DMBMPP

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DMBMPP, or 2-(2,5-dimethoxy-4-bromobenzyl)-6-(2-methoxyphenyl)piperidine, is a 2-benzylpiperidine analog of the hallucinogenic N-benzylphenethylamine 25B-NBOMe...

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Fluorenylmethyloxycarbonyl protecting group

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analysis of fluorescence. The Fmoc group is rapidly removed by base. Piperidine is usually preferred for Fmoc group removal as it forms a stable adduct...

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Arylcyclohexylamine

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such as methylamine or ethylamine, or tertiary cycloalkylamines such as piperidine and pyrrolidine, are the most commonly encountered N-substituents. Arylcyclohexylamines...

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Piperidine alkaloids

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Piperidine alkaloids are naturally occurring chemical compounds from the group of alkaloids, which are chemically derived from piperidine. Alkaloids with...

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Desoxypipradrol

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three of which share a similar pharmacological action. Of these three piperidines, desoxypipradrol has the longest elimination half-life, as it is a highly...

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List of benzimidazole opioids

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evidence on the use and harms of 2-benzyl benzimidazole ('nitazene') and piperidine benzimidazolone ('brorphine-like') opioids" (PDF). Advisory Council on...

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Molybdenum hexacarbonyl

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Mo(CO)5(THF). The thermal reaction of Mo(CO)6 with piperidine affords Mo(CO)4(piperidine)2. The two piperidine ligands in this yellow-colored compound are labile...

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Benocyclidine

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Chicheportiche R (1998). "[3H]N-[1-(2-benzo(b)thiophenyl)cyclohexyl]piperidine ([3H]BTCP): a new phencyclidine analog selective for the dopamine uptake...

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Phencyclidine

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Phencyclidine or phenylcyclohexyl piperidine (PCP), also known in its use as a street drug as angel dust among other names, is a dissociative anesthetic...

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Azacyclonol

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hydrogenation of the pyridine heteroaromatic ring system to the corresponding piperidine. Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes...

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Benzhydryl compounds

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or Bzh. Acyclic: pridinol Pyrolidino: diphenylprolinol 2-Piperidine: pipradrol 4-Piperidine: terfenadine, fexofenadine Benzilic ester: QNB, JB-336, JB-318...

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Controlled Drugs and Substances Act

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4-anilino-1-boc-piperidine (tert-butyl 4-(phenylamino)piperidine-1-carboxylate) 4-fluoro anilino-1-boc-piperidine (tert-butyl 4-((4-fluorophenyl)amino)piperidine-1-carboxylate)...

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Benzoyl chloride

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US1851832, 29 March 1932 Marvel, C. S.; Lazier, W. A. (1929). "Benzoyl Piperidine". Organic Syntheses. 9: 16. doi:10.15227/orgsyn.009.0016. Prasenjit Saha...

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Phenylpiperidines

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Phenylpiperidines are chemical compounds with a phenyl moiety directly attached to piperidine. There are a variety of pharmacological effects associated with phenylpiperidines...

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Hindered amine light stabilizers

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into a nitrone species and piperidines are resistant to intramolecular Cope reactions. In commercial HALS the reactive piperidine group is usually bonded...

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Piperazine

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Piperazines were originally named because of their chemical similarity with piperidine, part of the structure of piperine in the black pepper plant (Piper nigrum)...

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Icaridin

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has been approved by the WHO is icaridin. The chemical is part of the piperidine family, along with many pharmaceuticals and alkaloids such as piperine...

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Pethidine intermediate A

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Pethidine intermediate A is a 4-phenylpiperidine derivative that is a precursor to the opioid analgesic drug pethidine (meperidine). It is not known to...

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Adderall

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GBR-13098 GBR-13119 MeOPP MBZP oMPP Vanoxerine Piperidines 1-Benzyl-4-(2-(diphenylmethoxy)ethyl)piperidine 2-Benzylpiperidine 2-Methyl-3-phenylpiperidine...

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Methylphenidate

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is a central nervous system (CNS) stimulant of the phenethylamine and piperidine classes. It is available as a generic medication. In 2021, it was the...

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Pipecolic acid

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Pipecolic acid (piperidine-2-carboxylic acid) is an organic compound with the formula HNC5H9CO2H. It is a carboxylic acid derivative of piperidine and, as such...

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