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			{{short description|Alkaloid responsible for the pungency of black pepper}}
			{{distinguish|piperidine}}
	{{chembox		{{chembox
			| Verifiedfields = changed
⚫	| verifiedrevid = 394458921
			| Watchedfields = changed
⚫	| ImageFile1 = piperine1.png
		⚫	| verifiedrevid = 414843869
		⚫	| ImageFile1 = piperin.svg
	| ImageFile2 = Piperine_crystals.jpg		| ImageFile2 = Piperine_crystals.jpg
	| ImageName = Octane-3D-balls.png		| ImageName = Octane-3D-balls.png
	| IUPACName = <small>1-piperidine</small>		| PIN = (2''E'',4''E'')-5-(2''H''-1,3-Benzodioxol-5-yl)-1-(piperidin-1-yl)penta-2,4-dien-1-one
			| OtherNames = (2''E'',4''E'')-5-(Benzodioxol-5-yl)-1-(piperidin-1-yl)penta-2,4-dien-1-one<br />Piperoylpiperidine<br />Bioperine
	| OtherNames = <small>5-(3,4-methylenedioxyphenyl)-2,4-pentadienoyl-2-piperidine<br>piperoylpiperidine</small>
	| Section1 = {{Chembox Identifiers		| Section1 = {{Chembox Identifiers
			| IUPHAR_ligand = 2489
			| ChEBI_Ref = {{ebicite|changed|EBI}}
			| ChEBI = 28821
			| ChEMBL_Ref = {{ebicite|changed|EBI}}
			| ChEMBL = 43185
	| CASNo = 94-62-2		| CASNo = 94-62-2
	| CASNo_Ref = {{cascite|correct|CAS}}		| CASNo_Ref = {{cascite|correct|CAS}}
			| UNII_Ref = {{fdacite|changed|FDA}}
	| SMILES = O=C(/C=C/C=C/C2=CC=C<br />(OCO3)C3=C2)N1CCCCC1
			| UNII = U71XL721QK
			| PubChem = 638024
			| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
			| ChemSpiderID = 553590
			| SMILES = O=C(N1CCCCC1)\C=C\C=C\c2ccc3OCOc3c2
			| InChI = 1/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-YPCIICBEBY
			| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
			| StdInChI = 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+
			| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
			| StdInChIKey = MXXWOMGUGJBKIW-YPCIICBESA-N
	}}		}}
	| Section2 = {{Chembox Properties		| Section2 = {{Chembox Properties
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	| Density = 1.193 g/cm<sup>3</sup>		| Density = 1.193 g/cm<sup>3</sup>
	| MeltingPtC = 130		| MeltingPtC = 130
	| BoilingPt = ''decomposes''		| BoilingPt = Decomposes
	| pKa =		| pKa =
			| Solubility = 40{{nbsp}}mg/l
			| Solvent1 = ethanol
			| Solubility1 = soluble
			| Solvent2 = chloroform
			| Solubility2 = 1{{nbsp}}g/1.7{{nbsp}}ml
	}}		}}
	| Section3 = {{Chembox Hazards		| Section3 = {{Chembox Hazards
	| ExternalMSDS = }}		| ExternalSDS = }}
	}}		}}
			{{Infobox pepper
			| scoville = 150,000<ref>{{Cite book|url=https://books.google.com/books?id=2UQ8BAAAQBAJ|title=Pharmacognosy: An Indian perspective|last=Mangathayaru|first=K.|date=2013|publisher=Pearson Education India|isbn=9789332520264|pages=274|language=en}}</ref>
			}}
			'''Piperine''', possibly along with its ] ],<ref name="De_Cleyn&Verzele1972" /> is the compound<ref>{{Merck11th|page=7442}}</ref> responsible for the ] of ] and ]. It has been used in some forms of ].<ref>{{cite journal |title=Black pepper and its pungent principle-piperine: A review of diverse physiological effects
			|author=Srinivasan, K.|doi=10.1080/10408390601062054|journal=Critical Reviews in Food Science and Nutrition|volume=47|year=2007|issue=8|pages=735–748|pmid=17987447|s2cid=42908718}}</ref>
		⚫	==Preparation==
	:''For the organic compound used in drug production, see: ]''
			Due to its poor solubility in water, piperine is typically extracted from ] by using organic solvents like ].<ref>{{cite journal | title = Isolation of Piperine from Black Pepper | last1 = Epstein | first1 = William W. | last2 = Netz | first2 = David F. | last3 = Seidel | first3 = Jimmy L. | year = 1993 | volume = 70 | pages = 598 | journal = ] | doi = 10.1021/ed070p598 | issue = 7| bibcode = 1993JChEd..70..598E }}</ref> The amount of piperine varies from 1–2% in long pepper, to 5–10% in commercial white and black peppers.<ref>{{cite web|url=http://www.tis-gdv.de/tis_e/ware/gewuerze/pfeffer/pfeffer.htm#selbsterhitzung|title=Pepper|website=Tis-gdv.de|access-date=2 September 2017}}</ref><ref name="henry">{{cite book |last=Henry |first=Thomas Anderson |title=The Plant Alkaloids |date=1949 |publisher=The Blakiston Company |isbn= |edition=4th |location= |page= |pages=35-37 |section=Piperine}}</ref>
			Piperine can also be prepared by treating the solvent-free residue from a concentrated alcoholic extract of black pepper with a solution of ] to remove resin (said to contain ], an isomer of piperine).<ref name=henry>{{cite book |last=Henry |first=Thomas Anderson |date=1949 |edition=4th |title=The Plant Alkaloids |location= |publisher=The Blakiston Company |page=1-2 |section=Piperine |isbn=}}</ref> The solution is decanted from the insoluble residue and left to stand overnight in alcohol. During this period, the alkaloid slowly ] from the solution.<ref>{{cite book|last=Ikan|first=Raphael | title = Natural Products: A Laboratory Guide |edition=2nd |year=1991|publisher=Academic Press|location=San Diego, CA|isbn=0123705517|pages=223–224|url=https://books.google.com/books?id=B7P8HQimBAIC&q=Natural+Products%3A+A+Laboratory+Guide+2nd+Ed.}}</ref>
⚫	'''Piperine''' is the ]<ref>''Merck Index'', 11th Edition, '''7442'''</ref> responsible for the ] of ] and ], along with ] (an ] of piperine). It has also been used in some forms of ] and as an ]. Piperine forms ] needles, is slightly soluble in water and more so in ], ] or ]: the solution in alcohol has a pepper-like taste. It yields salts only with strong acids. The platinichloride B<sub>4</sub>•H<sub>2</sub>PtCl<sub>6</sub> forms orange-red needles. ("B" denotes one mole of the alkaloid base in this and the following formulae.) ] in ] added to an alcoholic solution of the base in presence of a little ] gives a characteristic periodide, B<sub>2</sub>•HI•I<sub>2</sub>, crystallising in steel-blue needles, mp. 145°C.
	Anderson<ref>''Annalen,'' 1850, '''75,''' 82; '''84,''' 345, ''cf.'' Wertheim and Rochleder, ''ibid.,'' 1845, '''54,''' 255.</ref> first hydrolysed piperine by alkalis into a base and an acid, which were later named<ref>Babo & Keller, ''Journ. pr. chem.,'' 1857, '''72,''' 53.</ref> ] and ] respectively. The alkaloid was synthesised<ref>Rugheimer, ''Ber.,'' 1882, '''15,''' 1390.</ref> by the action of piperoyl chloride on piperidine.
			Piperine has been synthesized by the action of ] on ].<ref name=henry />
⚫	==Preparation==
	Piperine is commercially available. If desired, it may be extracted from ] using ].<ref>{{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 = ] | doi = 10.1021/ed070p598}}</ref> The amount of piperine varies from 1-2% in long pepper, to 5-9% in the white and the black peppers of commerce.<ref>http://www.tis-gdv.de/tis_e/ware/gewuerze/pfeffer/pfeffer.htm#selbsterhitzung</ref> Further, it may be prepared by treating the solvent-free residue from an alcoholic extract of ], with a solution of ] to remove resin (said to contain ], an isomer of piperine) and solution of the washed, insoluble residue in warm alcohol, from which the alkaloid crystallises on cooling.{{Citation needed|date=September 2009}}
			==Reactions==
	==Biological activity==
		⚫	Piperine forms salts only with strong acids. The ] B<sub>4</sub>·H<sub>2</sub>PtCl<sub>6</sub> forms orange-red needles ("B" denotes one mole of the alkaloid base in this and the following formula). ] in ] added to an alcoholic solution of the base in the presence of a little ] gives a characteristic periodide, B<sub>2</sub>·HI·I<sub>2</sub>, crystallizing in steel-blue needles with ] 145&nbsp;°C.<ref name=henry />
	The pungency caused by ] and piperine is caused by activation of the heat and acidity sensing ] ] ] on ] (pain sensing ]).<ref name="pmid15685214">{{cite journal |author=McNamara FN, Randall A, Gunthorpe MJ |title=Effects of piperine, the pungent component of black pepper, at the human vanilloid receptor (TRPV1) |journal=Br. J. Pharmacol. |volume=144 |issue=6 |pages=781–90 |year=2005 |month=March |pmid=15685214 |pmc=1576058 |doi=10.1038/sj.bjp.0706040 |url=}}</ref>
			Piperine can be ] by an alkali into ] and ].<ref name=henry />
	Piperine has also been found to inhibit human ] and ], ]s important for the ] and transport of ]s and ]s.<ref>{{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=}}</ref> In animal studies, piperine also inhibited other enzymes important in drug metabolism.<ref name=Atal>{{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}}</ref><ref>{{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= 10.1016/0006-2952(93)90408-O|url=}}</ref> By inhibiting drug metabolism, piperine may increase the ] of various compounds and alter the effectiveness of some medications.<ref name=Atal/> Notably, piperine may enhance bioavailability of ] by 2000% in humans.<ref>{{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= 10.1055/s-2006-957450|url=}}</ref>
			In light, especially ], piperine is changed into its isomers ], isochavicine and isopiperine, which are tasteless.<ref name="Kozukue_et_al_2007">{{cite journal |last1=Kozukue |first1=Nobuyuki |last2=Park |first2=Mal-Sun |last3=others |first3=and 5 |title=Kinetics of Light-Induced Cis−Trans Isomerization of Four Piperines and Their Levels in Ground Black Peppers as Determined by HPLC and LC/MS |journal=J. Agric. Food Chem. |date=2007 |volume=55 |issue=17 |pages=7131–7139 |doi=10.1021/jf070831p |pmid=17661483 |url=https://doi.org/10.1021/jf070831p |access-date=26 September 2023}}</ref><ref name="De_Cleyn&Verzele1972">{{cite journal |last1=De Cleyn |first1=R |last2=Verzele |first2=M |title=Constituents of peppers. I Qualitative Analysis of Piperine Isomers |journal=Chromatografia |date=1972 |volume=5 |pages=346–350 |doi=10.1007/BF02315254 |s2cid=56022338 |url=https://www.chm.bris.ac.uk/sillymolecules/chavicine.pdf |access-date=26 September 2023}}</ref>
	In February 2008, researchers discovered that piperine can stimulate pigmentation in the skin, together with the exposure to UVB light.<ref>{{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 | pmid = 18284389 | issue = 5}}</ref><ref>{{cite news | publisher = ] | title = Pepper 'to treat pigment disease' | url = http://news.bbc.co.uk/1/hi/health/7244474.stm | date = 2008-02-14}}</ref>
			==History==
	Piperine was discovered by ] in 1819, he isolated it from the fruits of ], the source plant of both the black and white pepper grains.<ref>Oersted, "Über das Piperin, ein neues Pflanzenalkaloid" , ''(Schweigger's) Journal für Chemie und Physik'', vol. 29, no. 1, pages 80-82 (1820). Available on-line (in German): http://books.google.com/books?id=k-M4AAAAMAAJ&pg=PA80&lpg=PA81&ots=BOH_h5pA3s&ie=ISO-8859-1&output=html .</ref> ] and ] (Miq.) C. DC. (=Piper retrofractum Vahl), two species called "long pepper" also found containing it by Flückiger and Hanbury.<ref>''Pharmacographia'' (London: Macmillan & Co., 1879), p. 584.</ref> ] also contains it.<ref>Stenhouse in ''Pharm. J.,'' 1855, 14, 363.</ref>
			Piperine was discovered in 1819 by ], who isolated it from the fruits of '']'', the source plant of both black and white pepper.<ref>{{cite journal|last=Ørsted |first=Hans Christian |author-link=Hans Christian Ørsted |url=https://books.google.com/books?id=k-M4AAAAMAAJ&pg=PA80 |title=Über das Piperin, ein neues Pflanzenalkaloid|language=de |trans-title=On piperine, a new plant alkaloid |journal=Schweiggers Journal für Chemie und Physik |volume= 29 |issue= 1 |pages=80–82 |date=1820}}</ref> Piperine was also found in '']'' and '']'' (Miq.) C. DC. (=''Piper retrofractum'' Vahl), two species called "long pepper".<ref>{{cite book|title=Pharmacographia : a History of the Principal Drugs of Vegetable Origin, Met with in Great Britain and British India|url=https://archive.org/details/pharmacographia01hanbgoog|author1=Friedrich A. Fluckiger|author2=Daniel Hanbury|location=London|publisher=Macmillan|date=1879|page=|asin=B00432KEP2}}</ref>
	==See also==		== See also ==
	*], a cyclic six-membered ] that results from ] of piperine		*], a cyclic six-membered ] that results from ] of piperine
			*], the ] also derived from hydrolysis of piperine
	*], the active piquant chemical in ]s		*], the active piquant chemical in ]s
	*], the active ] chemical in ], ]es, ], and ]		*], the active ] chemical in ], ]es, ], and ]
	*], the active piquant flavor chemical in raw ] and ] (see those articles for discussion of other chemicals in them relating to pungency, and eye irritation)		*], the active piquant flavor chemical in raw ] and ] (see those articles for discussion of other chemicals in them relating to pungency, and eye irritation)
			*]
			*]
	==References==		== References ==
	{{Reflist}}		{{Reflist|30em}}
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