PIPERAMIDE

Details

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

SHOW SMILES / InChI

Structure Search

SMILES

CN(C)CCCN1CCN(CC1)C2=CC=C(NC(C)=O)C=C2

InChI

InChIKey=DPCSPGOPQYRPCP-UHFFFAOYSA-N

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

HIDE SMILES / InChI

Molecular Formula	C17H28N4O
Molecular Weight	304.4304
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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
Synthesis and nematocidal activity of aralkyl- and aralkenylamides related to piperamide on second-stage larvae of Toxocara canis.	1997 Apr	9145505
New optimized piperamide analogues with potent in vivo hypotensive properties.	2004 Dec	15567289
Analysis of Piperaceae germplasm by HPLC and LCMS: a method for isolating and identifying unsaturated amides from Piper spp extracts.	2005 Mar 23	15769112
Analysis by HPLC and LC/MS of pungent piperamides in commercial black, white, green, and red whole and ground peppercorns.	2008 May 14	18386929
Cardiovascular effects of a novel synthetic analogue of naturally occurring piperamides.	2010 Sep	20571426
Synthesis and biological evaluation of piperamide analogues as HDAC inhibitors.	2011 Aug 15	21745740
Practical and efficient approach to the synthesis of guineensine.	2011 Feb	21279876
The distributional nexus of choroid plexus to cerebrospinal fluid, ependyma and brain: toxicologic/pathologic phenomena, periventricular destabilization, and lesion spread.	2011 Jan	21189316
Bioassay-guided isolation of constituents of Piper sarmentosum using a mitochondrial transmembrane potential assay.	2011 Oct 28	21973101
Synthesis, characterization, antidepressant and antioxidant activity of novel piperamides bearing piperidine and piperazine analogues.	2012 Dec 1	23079521
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	23561585
Alkaloids from Piper nigrum Exhibit Antiinflammatory Activity via Activating the Nrf2/HO-1 Pathway.	2017 Apr	28185326
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 ethnobotanical survey and antifungal activity of Piper guineense used for the treatment of fungal infections in West-African traditional medicine.	2019 Jan 30	30336302

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:14:39 UTC 2023` Edited by `admin` on `Fri Dec 15 16:14:39 UTC 2023`
Record UNII	83B7UZO20C
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

PIPERAMIDE

Official Name

English

ACETAMIDE, N-(4-(4-(3-(DIMETHYLAMINO)PROPYL)-1-PIPERAZINYL)PHENYL)-

Systematic Name

English

piperamide [INN]

Common Name

English

4'-(4-(3-(DIMETHYLAMINO)PROPYL)-1-PIPERAZINYL)ACETANILIDE

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C250