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Details

Stereochemistry ACHIRAL
Molecular Formula C17H19NO3
Molecular Weight 285.3377
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 2
Charge 0

SHOW SMILES / InChI
Structure of PIPERINE

SMILES

O=C(\C=C\C=C\C1=CC2=C(OCO2)C=C1)N3CCCCC3

InChI

InChIKey=MXXWOMGUGJBKIW-YPCIICBESA-N
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+

HIDE SMILES / InChI
Molecular Formula C17H19NO3
Molecular Weight 285.3377
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 2
Optical Activity NONE

Description
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/23625885

Piperine is a simple and pungent alkaloid found in the seeds of black pepper (Piper nigrum). Following its isolation and full characterization, the biological properties of piperine have been extensively studied, and piperine-like derivatives have shown an interesting range of pharmacological activities. Piperine is currently paving its way to become a privileged scaffold for the development of bioactive compounds with therapeutic application in multiple human diseases. In particular, piperine derivatives were shown to modulate the activity of several targets related to neurological disorders, including epilepsy, Parkinson's disease, depression and pain related disorders. Moreover, the efflux pump inhibitory ability of piperine and its analogues tackles important drug resistance mechanisms and may improve the clinical efficacy of antibiotic and anticancer drugs. Piperine has been found to have immunomodulatory, anti-oxidant, anti-asthmatic, anti-carcinogenic, anti-inflammatory, anti-ulcer, and anti-amoebic properties.

CNS Activity

CNS Penetrant
2588
Curator's Comment: Blood-brain barrier penetrant and CNS active

Originator

Ørsted, H.C.
3
Curator's Comment: Piperine was discovered in 1819, when Hans Christian Ørsted isolated it from the fruits of the source plant of black and white pepper, piper nigrum. Piperine's chemical constitution was established by laboritory synthesis in 1882 and 1894.

Approval Year

2011
587
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8504
 14.19 µM [IC50]
Inhibitor
8504
 2.12 µM [IC50]
Inhibitor
8504
Inhibitor
8504
 133.3 µM [IC50]
Inhibitor
8504
 45.0 µM [IC50]
Inhibitor
8504
 230.7 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Phase II
1147
Unknown

Approved Use

Unknown
Palliative
Phase I
438
Unknown

Approved Use

Unknown
Doses

Doses

DosePopulationAdverse events​
24 mg 2 times / day multiple, oral
Highest studied dose
Dose: 24 mg, 2 times / day
Route: oral
Route: multiple
Dose: 24 mg, 2 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/22725836/
healthy, ADULT
Health Status: healthy
Age Group: ADULT
Sex: unknown
Food Status: FED
Sources:
https://pubmed.ncbi.nlm.nih.gov/22725836/
Sources:
https://pubmed.ncbi.nlm.nih.gov/22725836/
PubMed

PubMed

TitleDatePubMed
Piperine blocks interleukin-2-driven cell cycle progression in CTLL-2 T lymphocytes by inhibiting multiple signal transduction pathways.
2015-04-02
Screening of a chemical library reveals novel PXR-activating pharmacologic compounds.
2015-01-05
Mitigating efficacy of piperine in the physiological derangements of high fat diet induced obesity in Sprague Dawley rats.
2014-09-25
Piperine potentiates the antidepressant-like effect of trans-resveratrol: involvement of monoaminergic system.
2013-12
Piperine activates human pregnane X receptor to induce the expression of cytochrome P450 3A4 and multidrug resistance protein 1.
2013-10-01
Small molecule activators of the Nrf2-HO-1 antioxidant axis modulate heme metabolism and inflammation in BV2 microglia cells.
2013-10
Anti-HBV active constituents from Piper longum.
2013-04-01
Piperine inhibits PMA-induced cyclooxygenase-2 expression through downregulating NF-κB, C/EBP and AP-1 signaling pathways in murine macrophages.
2012-07
Suppression of phorbol-12-myristate-13-acetate-induced tumor cell invasion by piperine via the inhibition of PKCα/ERK1/2-dependent matrix metalloproteinase-9 expression.
2011-05-30
The plant alkaloid piperine as a potential inhibitor of ethidium bromide efflux in Mycobacterium smegmatis.
2011-02
Drug discovery for Duchenne muscular dystrophy via utrophin promoter activation screening.
2011
Piperine as an inhibitor of Rv1258c, a putative multidrug efflux pump of Mycobacterium tuberculosis.
2010-08
Antioxidant effects of a Rhodobryum roseum extract and its active components in isoproterenol-induced myocardial injury in rats and cardiac myocytes against oxidative stress-triggered damage.
2009-01
Identification of kaempferol as an inhibitor of cigarette smoke-induced activation of the aryl hydrocarbon receptor and cell transformation.
2007-03
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.
2006-11
Modulation of cadmium induced alterations in murine thymocytes by piperine: oxidative stress, apoptosis, phenotyping and blastogenesis.
2006-08-14
Effects of piperine, the pungent component of black pepper, at the human vanilloid receptor (TRPV1).
2005-03
Effects of xenobiotics and peroxisome proliferator-activated receptor-alpha on the human UDPglucose dehydrogenase gene expression.
2005
Piperine is a potent inhibitor of nuclear factor-kappaB (NF-kappaB), c-Fos, CREB, ATF-2 and proinflammatory cytokine gene expression in B16F-10 melanoma cells.
2004-12-20
Inhibition of MAO A and B by some plant-derived alkaloids, phenols and anthraquinones.
2004-04
Screening of the inhibitory effect of vegetable constituents on the aryl hydrocarbon receptor-mediated activity induced by 2,3,7,8-tetrachlorodibenzo-p-dioxin.
2003-12
Role of cytochrome P450 2B1 in puromycin aminonucleoside-induced cytotoxicity to glomerular epithelial cells.
2003
Steroid hormone activity of flavonoids and related compounds.
2000-07
Action of intrathecal capsaicin and its structural analogues on the content and release of spinal substance P: selectivity of action and relationship to analgesia.
1984-07-23
Patents

Patents

JP2005112846A
3
JP2011105715A
3
JPH08173083A
4

Sample Use Guides

In Vivo Use Guide
A single dose of Piperine 20 mg was administered daily for 10 days
Route of Administration: Oral
In Vitro Use Guide
Piperine inhibited the proliferation of SW480 and HT-29 cells in a dose-dependent manner, it had low cytotoxicity on these cell lines with 50 % inhibiting concentration (IC50) values greater than 100 uM. Pretreatment of the cells with 40 uM piperine for 1 h significantly inhibited the mRNA production of CXCL8 in response to LPS stimulation in SW480 and HT-29 cells.
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:15:15 GMT 2025
Edited
by admin
on Mon Mar 31 18:15:15 GMT 2025
Record UNII
U71XL721QK
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PIPERINE
FHFI   INCI   MI   USP-RS   WHO-DD  
INCI  
Official Name English
FEMA NO. 2909
Preferred Name English
PIPERINE [FHFI]
Common Name English
NSC-21727
Code English
PIPERINE [USP-RS]
Common Name English
BIOPERINE
Common Name English
PIPERINE (CONSTITUENT OF BLACK PEPPER) [DSC]
Common Name English
(E,E)-1-(5-(1,3-BENZODIOXOL-5-YL)-2,4-PENTADIENOYL)PIPERIDINE
Systematic Name English
PIPERINE [MI]
Common Name English
(2E,4E)-5-(Benzo[d][1,3]dioxol-5-yl)-1-(piperidin-1-yl)penta-2,4-dien-1-one
Systematic Name English
PIPERIDINE, 1-(5-(1,3-BENZODIOXOL-5-YL)-1-OXO-2,4-PENTADIENYL)-, (E,E)-
Common Name English
Piperine [WHO-DD]
Common Name English
Classification Tree Code System Code
DSLD 2372 (Number of products:123)
Created by admin on Mon Mar 31 18:15:15 GMT 2025 , Edited by admin on Mon Mar 31 18:15:15 GMT 2025
NCI_THESAURUS C257
Created by admin on Mon Mar 31 18:15:15 GMT 2025 , Edited by admin on Mon Mar 31 18:15:15 GMT 2025
JECFA EVALUATION PIPERINE
Created by admin on Mon Mar 31 18:15:15 GMT 2025 , Edited by admin on Mon Mar 31 18:15:15 GMT 2025
EPA PESTICIDE CODE 43501
Created by admin on Mon Mar 31 18:15:15 GMT 2025 , Edited by admin on Mon Mar 31 18:15:15 GMT 2025
CFR 21 CFR 172.515
Created by admin on Mon Mar 31 18:15:15 GMT 2025 , Edited by admin on Mon Mar 31 18:15:15 GMT 2025
Code System Code Type Description
PUBCHEM
638024
Created by admin on Mon Mar 31 18:15:15 GMT 2025 , Edited by admin on Mon Mar 31 18:15:15 GMT 2025
PRIMARY
NCI_THESAURUS
C72629
Created by admin on Mon Mar 31 18:15:15 GMT 2025 , Edited by admin on Mon Mar 31 18:15:15 GMT 2025
PRIMARY
FDA UNII
U71XL721QK
Created by admin on Mon Mar 31 18:15:15 GMT 2025 , Edited by admin on Mon Mar 31 18:15:15 GMT 2025
PRIMARY
CHEBI
28821
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PRIMARY
EVMPD
SUB35136
Created by admin on Mon Mar 31 18:15:15 GMT 2025 , Edited by admin on Mon Mar 31 18:15:15 GMT 2025
PRIMARY
MERCK INDEX
m8854
Created by admin on Mon Mar 31 18:15:15 GMT 2025 , Edited by admin on Mon Mar 31 18:15:15 GMT 2025
PRIMARY Merck Index
EPA CompTox
DTXSID3021805
Created by admin on Mon Mar 31 18:15:15 GMT 2025 , Edited by admin on Mon Mar 31 18:15:15 GMT 2025
PRIMARY
DAILYMED
U71XL721QK
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PRIMARY
CAS
94-62-2
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PRIMARY
DRUG BANK
DB12582
Created by admin on Mon Mar 31 18:15:15 GMT 2025 , Edited by admin on Mon Mar 31 18:15:15 GMT 2025
PRIMARY
MESH
C008922
Created by admin on Mon Mar 31 18:15:15 GMT 2025 , Edited by admin on Mon Mar 31 18:15:15 GMT 2025
PRIMARY
WIKIPEDIA
PIPERINE
Created by admin on Mon Mar 31 18:15:15 GMT 2025 , Edited by admin on Mon Mar 31 18:15:15 GMT 2025
PRIMARY
ChEMBL
CHEMBL43185
Created by admin on Mon Mar 31 18:15:15 GMT 2025 , Edited by admin on Mon Mar 31 18:15:15 GMT 2025
PRIMARY
RS_ITEM_NUM
1543200
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PRIMARY
SMS_ID
100000128291
Created by admin on Mon Mar 31 18:15:15 GMT 2025 , Edited by admin on Mon Mar 31 18:15:15 GMT 2025
PRIMARY
NSC
21727
Created by admin on Mon Mar 31 18:15:15 GMT 2025 , Edited by admin on Mon Mar 31 18:15:15 GMT 2025
PRIMARY
JECFA MONOGRAPH
1589
Created by admin on Mon Mar 31 18:15:15 GMT 2025 , Edited by admin on Mon Mar 31 18:15:15 GMT 2025
PRIMARY
RXCUI
1311146
Created by admin on Mon Mar 31 18:15:15 GMT 2025 , Edited by admin on Mon Mar 31 18:15:15 GMT 2025
PRIMARY RxNorm
GRAS Notification (GRN No.)
474
Created by admin on Mon Mar 31 18:15:15 GMT 2025 , Edited by admin on Mon Mar 31 18:15:15 GMT 2025
PRIMARY
ECHA (EC/EINECS)
202-348-0
Created by admin on Mon Mar 31 18:15:15 GMT 2025 , Edited by admin on Mon Mar 31 18:15:15 GMT 2025
PRIMARY
Related Record Type Details
Structure of ILEPCIMIDE
DERIVATIVE -> PARENT
PIPER LONGUM FRUIT EXTRACT
PARENT -> CONSTITUENT ALWAYS PRESENT
PIPER RETROFRACTUM FRUIT POWDER
PARENT -> CONSTITUENT ALWAYS PRESENT
BLACK PEPPER
PARENT -> CONSTITUENT ALWAYS PRESENT
Related Record Type Details
Structure of PIPERINE
ACTIVE MOIETY
NIH
NCATS
PRIVACY NOTICE
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
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