Piperine

Chembox new
ImageFile = Piperine_crystals.jpg
ImageFile1 = piperine1.png ImageName =
IUPACName = 1- [5-(1,3-Benzodioxol-5-yl)-1-oxo-
2,4-pentadienyl] piperidine
Section1 = Chembox Identifiers
CASNo = 94-62-2
SMILES = O=C(/C=C/C=C/C2=CC=C
(OCO3)C3=C2)N1CCCCC1
Section2 = Chembox Properties
Formula = C₁₇H₁₉NO₃
MolarMass = 285.338 g/mol
Density = 1.193 g/cm³
MeltingPt = 130 °C
BoilingPt = "decomposes"
pKa = 1.98 [cite book |title=Profiles of Drug Substances, Excipients and Related Methodology, volume 33: Critical Compilation of Pka Values for Pharmaceutical Substances |author=Harry G. Brittain, Richard J. Prankerd |publisher=Academic Press |year=2007 |isbn=012260833X]
Section3 = Chembox Hazards
ExternalMSDS = [http://www.sciencelab.com/xMSDS-Piperine-9926579#search=%22piperine%20MSDS%22 MSDS for piperine]

Piperine is the alkaloid ["Merck Index", 11th Edition, 7442] responsible for the pungency of black pepper and long pepper, along with chavicine (an isomer of piperine). It has also been used in some forms of traditional medicine and as an insecticide.

Preparation

Piperine is commercially available. If desired, it may be extracted from black pepper using dichloromethane. [cite journal | title = Isolation of piperine from black pepper | author = Epstein, William W.; Netz, David F.; Seidel, Jimmy L. | year = 1993 | volume = 70 | pages = 598 | journal = J. Chem. Ed.]

Biological activity

The pungency caused by capsaicin and piperine is caused by activation of the heat and acidity sensing TRPV ion channel TRPV1 on nociceptors (pain sensing nerve cells).

Piperine has also been found to inhibit human CYP3A4 and P-glycoprotein, enzymes important for the metabolism and transport of xenobiotics and metabolites. [cite journal |author=Bhardwaj RK, Glaeser H, Becquemont L, Klotz U, Gupta SK, Fromm MF |title=Piperine, a major constituent of black pepper, inhibits human P-glycoprotein and CYP3A4 |journal=J. Pharmacol. Exp. Ther. |volume=302 |issue=2 |pages=645–50 |year=2002 |month=August |pmid=12130727 |doi=10.1124/jpet.102.034728 |url=] In animal studies, piperine also inhibited other enzymes important in drug metabolism. [cite journal |author=Atal CK, Dubey RK, Singh J |title=Biochemical basis of enhanced drug bioavailability by piperine: evidence that piperine is a potent inhibitor of drug metabolism |journal=J. Pharmacol. Exp. Ther. |volume=232 |issue=1 |pages=258–62 |year=1985 |month=January |pmid=3917507 |doi= |url=http://jpet.aspetjournals.org/cgi/pmidlookup?view=long&pmid=3917507] [cite journal |author=Reen RK, Jamwal DS, Taneja SC, "et al" |title=Impairment of UDP-glucose dehydrogenase and glucuronidation activities in liver and small intestine of rat and guinea pig in vitro by piperine |journal=Biochem. Pharmacol. |volume=46 |issue=2 |pages=229–38 |year=1993 |month=July |pmid=8347144 |doi= |url=] By inhibiting drug metabolism, piperine may increase the bioavailability of various compounds. Notably, piperine may enhance bioavailability of curcumin by 2000% in humans. [cite journal |author=Shoba G, Joy D, Joseph T, Majeed M, Rajendran R, Srinivas PS |title=Influence of piperine on the pharmacokinetics of curcumin in animals and human volunteers |journal=Planta Med. |volume=64 |issue=4 |pages=353–6 |year=1998 |month=May |pmid=9619120 |doi= |url=]

In February 2008, researchers discovered that piperine can stimulate pigmentation in the skin. [cite journal | doi = 10.1111/j.1365-2133.2008.08464.x | title = In vivo evaluation of piperine and synthetic analogues as potential treatments for vitiligo using a sparsely pigmented mouse model | year = 2008 | author = Faas, L.; Venkatasamy, R.; Hider, R. C.; Young, A. R.; Soumyanath, A. | journal = British Journal of Dermatology | volume = 158 | pages = 941] [cite news | publisher = BBC News | title = Pepper 'to treat pigment disease' | url = http://news.bbc.co.uk/1/hi/health/7244474.stm | date = 2008-02-14]

Due to its effects on drug metabolism, piperine should be taken cautiously (if at all) by individuals taking some other medications.

Piperine was first discovered by Hans Christian Ørsted in 1819.Fact|date=June 2008

ee also

* Piperidine, a cyclic six-membered amine that results from hydrolysis of piperine
* Capsaicin, the active piquant chemical in chili peppers
* Allyl isothiocyanate, the active piquant chemical in mustard, radishes, horseradish and wasabi
* Allicin, the active piquant flavor chemical in uncooked garlic and onions (see those articles for discussion of other chemicals in them relating to pungency, and eye irritation)

References

External links

* [http://www.pdrhealth.com/drug_info/nmdrugprofiles/nutsupdrugs/pip_0322.shtml PDRhealth.com] - Piperine