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Substance Name: Piperine [USP]
RN: 94-62-2
UNII: U71XL721QK
InChIKey: MXXWOMGUGJBKIW-YPCIICBESA-N

Note

  • More potent than vanilloid (capsaicin) at human TRPV1; used to increase gastrointestinal assimilation of other agents.

Molecular Formula

  • C17-H19-N-O3

Molecular Weight

  • 285.3411
 

Classification Codes

  • Cytochrome P-450 Enzyme Inhibitors
  • Drug / Therapeutic Agent
  • Enzyme Inhibitors
  • Reproductive Effect
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Names and Synonyms

Name of Substance

  • Piperine [USP]

Synonyms

  • 1,3-Benzodioxol-5-yl-1-oxo-2,4-pentadienyl-piperine
  • 1-(5-(1,3-Benzodioxol-5-yl)-1-oxo-2,4-pentadienyl)piperidine, (E,E)-
  • 1-Piperoylpiperidine
  • 1-Piperoylpiperidine, (E,E)-
  • Bioperine
  • CCRIS 5572
  • EINECS 202-348-0
  • FEMA No. 2909
  • NSC 21727
  • Piperidine, 1-(5-(1,3-benzodioxol-5-yl)-1-oxo-2,4-pentadienyl)-, (E,E)-
  • Piperidine, 1-piperoyl-, (E,E)-
  • Piperin
  • Piperine
  • Piperoylpiperidine
  • UNII-U71XL721QK

Systematic Names

  • 2,4-Pentadien-1-one, 5-(1,3-benzodioxol-5-yl)-1-(1-piperidinyl)-, (2E,4E)-
  • Piperidine, 1-((2E,4E)-5-(1,3-benzodioxol-5-yl)-1-oxo-2,4-pentadienyl)-
  • Piperidine, 1-(5-(1,3-benzodioxol-5-yl)-1-oxo-2,4-pentadienyl)-, (E,E)- (9CI)
  • Piperidine, 1-piperoyl-, (E,E)-
  • Piperine

Superlist Name

  • Piperine

Registry Numbers

CAS Registry Number

  • 94-62-2

FDA UNII

  • U71XL721QK

Other Registry Number

  • 147030-08-8

System Generated Number

  • 0000094622

Structure Descriptors

InChI

1S/C17H19NO3/c19-17(18-10-4-1-5-11-18)7-3-2-6-14-8-9-15-16(12-14)21-13-20-15/h2-3,6-9,12H,1,4-5,10-11,13H2/b6-2+,7-3+

InChIKey

MXXWOMGUGJBKIW-YPCIICBESA-N

Smiles

c12c(ccc(c1)\C=C\C=C\C(N1CCCCC1)=O)OCO2

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
hamster LD50 intraperitoneal 105mg/kg (105mg/kg) BEHAVIORAL: EXCITEMENT

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Toxicology Letters. Vol. 16, Pg. 351, 1983.
mouse LD50 intramuscular 400ug/kg (0.4mg/kg) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES Toxicology Letters. Vol. 16, Pg. 351, 1983.
mouse LD50 intraperitoneal 43mg/kg (43mg/kg) BEHAVIORAL: EXCITEMENT

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)
Toxicology Letters. Vol. 16, Pg. 351, 1983.
mouse LD50 intravenous 15100ug/kg (15.1mg/kg) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES Toxicology Letters. Vol. 16, Pg. 351, 1983.
mouse LD50 oral 330mg/kg (330mg/kg) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES Toxicology Letters. Vol. 16, Pg. 351, 1983.
mouse LD50 subcutaneous 200mg/kg (200mg/kg) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES Toxicology Letters. Vol. 16, Pg. 351, 1983.
rat LD50 intraperitoneal 34mg/kg (34mg/kg) BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

BEHAVIORAL: EXCITEMENT

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Toxicology Letters. Vol. 16, Pg. 351, 1983.
rat LD50 oral 514mg/kg (514mg/kg) BEHAVIORAL: EXCITEMENT

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Toxicology Letters. Vol. 16, Pg. 351, 1983.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 131.5 deg C   EXP
log P (octanol-water) 3.690 (none)   EST
Water Solubility 40 mg/L 18 EXP
Vapor Pressure 1.30E-07 mm Hg 25 EST
Henry's Law Constant 1.93E-12 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 9.80E-11 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.