PIPERAMIDE MALEATE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C17H28N4O.2C4H4O4
Molecular Weight	536.5747
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	2
Charge	0

SHOW SMILES / InChI

Structure Search

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/4970351 | https://www.ncbi.nlm.nih.gov/pubmed/21189316 | Spencer, P.S., Schaumburg, H.H. (1980) Experimental and Clinical Neurotoxicology, page 604, retrieved from: https://books.google.ru/books?id=RL9rAAAAMAAJ | Elks, J. (2014) The Dictionary of Drugs: Chemical Data, page 987, retrieved from: https://books.google.ru/books?id=0vXTBwAAQBAJ

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

Title	Date	PubMed
Piperamide-induced morphological changes in the choroid plexus.	1968 Aug	4970351
Analysis by HPLC and LC/MS of pungent piperamides in commercial black, white, green, and red whole and ground peppercorns.	2008 May 14	18386929
The distributional nexus of choroid plexus to cerebrospinal fluid, ependyma and brain: toxicologic/pathologic phenomena, periventricular destabilization, and lesion spread.	2011 Jan	21189316
Synthesis, characterization, antidepressant and antioxidant activity of novel piperamides bearing piperidine and piperazine analogues.	2012 Dec 1	23079521
Mode of action of piperovatine, an insecticidal piperamide isolated from Piper piscatorum (Piperaceae), against voltage-gated sodium channels.	2018 Dec	30098356
Impact of novel N-aryl piperamide NO donors on NF-κB translocation in neuroinflammation: rational drug-designing synthesis and biological evaluation.	2018 Jan	29145791
Alkaloid-Rich Crude Extracts, Fractions and Piperamide Alkaloids of Piper guineense Possess Promising Antibacterial Effects.	2018 Nov 9	30423994
A systematic review on black pepper (Piper nigrum L.): from folk uses to pharmacological applications.	2019	30740986
An unprecedented chlorine-containing piperamide from Piper pseudoarboreum as potential leishmanicidal agent.	2019 Apr	30840916
An ethnobotanical survey and antifungal activity of Piper guineense used for the treatment of fungal infections in West-African traditional medicine.	2019 Jan 30	30336302
Antimicrobial and Synergistic Effects of Commercial Piperine and Piperlongumine in Combination with Conventional Antimicrobials.	2019 May 4	31060239

Name

Type

Language

PIPERAMIDE MALEATE

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