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Details

Stereochemistry ACHIRAL
Molecular Formula C17H28N4O.2C4H4O4
Molecular Weight 536.5747
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 2
Charge 0

SHOW SMILES / InChI
Structure of PIPERAMIDE MALEATE

SMILES

OC(=O)\C=C/C(O)=O.OC(=O)\C=C/C(O)=O.CN(C)CCCN1CCN(CC1)C2=CC=C(NC(C)=O)C=C2

InChI

InChIKey=YCPXMJXDVLKMIU-SPIKMXEPSA-N
InChI=1S/C17H28N4O.2C4H4O4/c1-15(22)18-16-5-7-17(8-6-16)21-13-11-20(12-14-21)10-4-9-19(2)3;2*5-3(6)1-2-4(7)8/h5-8H,4,9-14H2,1-3H3,(H,18,22);2*1-2H,(H,5,6)(H,7,8)/b;2*2-1-

HIDE SMILES / InChI

Molecular Formula C17H28N4O
Molecular Weight 304.4304
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C4H4O4
Molecular Weight 116.0722
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Description

Piperamide is substituted piperazine with a tertiary amine group. It was used as an anthelmintic agent. Initially, it was investigated because of its effectiveness against Trypanosoma. Piperamide distorts choroid plexus epithelial ultrastructure by engendering hydropic vacuoles.

Approval Year

PubMed

PubMed

TitleDatePubMed
Piperamide-induced morphological changes in the choroid plexus.
1968 Aug
Synthesis and nematocidal activity of aralkyl- and aralkenylamides related to piperamide on second-stage larvae of Toxocara canis.
1997 Apr
New optimized piperamide analogues with potent in vivo hypotensive properties.
2004 Dec
Analysis of Piperaceae germplasm by HPLC and LCMS: a method for isolating and identifying unsaturated amides from Piper spp extracts.
2005 Mar 23
Analysis by HPLC and LC/MS of pungent piperamides in commercial black, white, green, and red whole and ground peppercorns.
2008 May 14
Cardiovascular effects of a novel synthetic analogue of naturally occurring piperamides.
2010 Sep
Synthesis and biological evaluation of piperamide analogues as HDAC inhibitors.
2011 Aug 15
Practical and efficient approach to the synthesis of guineensine.
2011 Feb
The distributional nexus of choroid plexus to cerebrospinal fluid, ependyma and brain: toxicologic/pathologic phenomena, periventricular destabilization, and lesion spread.
2011 Jan
Bioassay-guided isolation of constituents of Piper sarmentosum using a mitochondrial transmembrane potential assay.
2011 Oct 28
Synthesis, characterization, antidepressant and antioxidant activity of novel piperamides bearing piperidine and piperazine analogues.
2012 Dec 1
In vitro schistosomicidal effects of aqueous and dichloromethane fractions from leaves and stems of Piper species and the isolation of an active amide from P. amalago L. (Piperaceae).
2014 Sep
Alkaloids from Piper nigrum Exhibit Antiinflammatory Activity via Activating the Nrf2/HO-1 Pathway.
2017 Apr
Mode of action of piperovatine, an insecticidal piperamide isolated from Piper piscatorum (Piperaceae), against voltage-gated sodium channels.
2018 Dec
Impact of novel N-aryl piperamide NO donors on NF-κB translocation in neuroinflammation: rational drug-designing synthesis and biological evaluation.
2018 Jan
Alkaloid-Rich Crude Extracts, Fractions and Piperamide Alkaloids of Piper guineense Possess Promising Antibacterial Effects.
2018 Nov 9
A systematic review on black pepper (Piper nigrum L.): from folk uses to pharmacological applications.
2019
An unprecedented chlorine-containing piperamide from Piper pseudoarboreum as potential leishmanicidal agent.
2019 Apr
An ethnobotanical survey and antifungal activity of Piper guineense used for the treatment of fungal infections in West-African traditional medicine.
2019 Jan 30
Antimicrobial and Synergistic Effects of Commercial Piperine and Piperlongumine in Combination with Conventional Antimicrobials.
2019 May 4
Substance Class Chemical
Created
by admin
on Tue Oct 22 06:12:20 UTC 2019
Edited
by admin
on Tue Oct 22 06:12:20 UTC 2019
Record UNII
7T952LZM7T
Record Status Validated (UNII)
Record Version
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Name Type Language
PIPERAMIDE MALEATE
USAN  
USAN  
Official Name English
CL-54131
Code English
CL 54131
Code English
4'-(4-(3-(DIMETHYLAMINO)PROPYL)-1-PIPERAZINYL)ACETANILIDE MALEATE (1:2)
Systematic Name English
ACETAMIDE, N-(4-(4-(3-(DIMETHYLAMINO)PROPYL)-1-PIPERAZINYL)PHENYL)-, (2Z)-2-BUTENEDIOATE (1:2)
Systematic Name English
PIPERAMIDE MALEATE [USAN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C250
Created by admin on Tue Oct 22 06:12:20 UTC 2019 , Edited by admin on Tue Oct 22 06:12:20 UTC 2019
Code System Code Type Description
ChEMBL
CHEMBL1945318
Created by admin on Tue Oct 22 06:12:20 UTC 2019 , Edited by admin on Tue Oct 22 06:12:20 UTC 2019
PRIMARY
NCI_THESAURUS
C66397
Created by admin on Tue Oct 22 06:12:20 UTC 2019 , Edited by admin on Tue Oct 22 06:12:20 UTC 2019
PRIMARY
PUBCHEM
20057141
Created by admin on Tue Oct 22 06:12:20 UTC 2019 , Edited by admin on Tue Oct 22 06:12:20 UTC 2019
PRIMARY
CAS
1252-69-3
Created by admin on Tue Oct 22 06:12:20 UTC 2019 , Edited by admin on Tue Oct 22 06:12:20 UTC 2019
PRIMARY
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ACTIVE MOIETY