A natural alkaloid with diverse biological actions
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Piperine

Item No. 11750

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(2E,4E)-5-(1,3-benzodioxol-5-yl)-1-(1-piperidinyl)-2,4-pentadien-1-one
CAS Number
94-62-2
Synonyms
  • Bioperine
  • NSC 21727
  • N-Piperoylpiperidin
Molecular Formula
C17H19NO3
Formula Weight
285.3
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 10 mg/mlDMSO: 10 mg/mlDMSO:PBS (pH 7.2) (1:7): 0.1 mg/mlEthanol: 10 mg/ml
λmax
255, 310, 345 nm
SMILES
O=C(/C=C/C=C/C1=CC(OCO2)=C2C=C1)N3CCCCC3
InChi Code
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+
InChi Key
MXXWOMGUGJBKIW-YPCIICBESA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
Certificates of Analysis & Batch Specific Data

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    5 g

    $33

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    10 g

    $62

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    25 g

    $118

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    100 g

    $279

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    Product Description

    Piperine is a natural alkaloid that can be isolated from black pepper. It activates transient receptor potential vanilloid type 1 receptor (TRPV1; EC50 = 38 µM) and modulates GABAA receptors (EC50s = 43-60 µM).1,2 At similar levels, piperine inhibits both monoamine oxidases (MAOs), with IC50 values of 21 and 7 µM for MAO-A and MAO-B, respectively.3 Like other natural compounds containing methylenedioxyphenyl substituents, piperine affects cytochrome P450 (CYP) isoforms, inhibiting CYP3A species (Ki ~ 5 µM) and increasing expression of CYP1A and CYP2B in liver.4 It also has a biphasic effect on P-glycoprotein activity.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. McNamara, F.N., Randall, A., and Gunthorpe, M.J. Effects of piperine, the pungent component of black pepper, at the human vanilloid receptor (TRPV1). Br. J. Pharmacol. 144(6), 781-790 (2005).

    2. Schöffmann, A., Wimmer, L., Goldman, D., et al. Efficient modulation of γ-aminobutyric acid type A receptors by piperine derivatives. J. Med. Chem. 57(37), 5602-5619 (2014).

    3. Lee, S.A., Hong, S.S., Han, X.H., et al. Piperine from the fruits of Piper longum with inhibitory effect on monoamine oxidase and antidepressant-like activity. Chem. Pharm. Bull. (Tokyo) 53(7), 832-835 (2005).

    4. Murray, M. Toxicological actions of plant-derived and anthropogenic methylenedioxyphenyl-substituted chemicals in mammals and insects. J. Toxicol. Environ. Health B Crit. Rev. 15(6), 365-395 (2012).

    5. Najar, I.A., Sachin, B.S., Sharma, S.C., et al. Modulation of P-glycoprotein ATPase activity by some phytoconstituents. Phytother. Res. 24(3), 454-458 (2010).