NONIVAMIDE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C17H27NO3
Molecular Weight	293.4012
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCCCCCCCC(=O)NCC1=CC=C(O)C(OC)=C1

InChI

InChIKey=RGOVYLWUIBMPGK-UHFFFAOYSA-N

InChI=1S/C17H27NO3/c1-3-4-5-6-7-8-9-17(20)18-13-14-10-11-15(19)16(12-14)21-2/h10-12,19H,3-9,13H2,1-2H3,(H,18,20)

HIDE SMILES / InChI

Description
Sources: https://gp2u.com.au/static/pdf/F/FINALGON-PI.pdf
Curator's Comment: Description was created based on several sources, including http://www.aversiontech.com/hot-and-spicy/nonivamide-pava/?gclid=CPb2kbG98M4CFULecgodQzgPcg and http://www.ema.europa.eu/docs/en_GB/document_library/Maximum_Residue_Limits_-_Report/2009/11/WC500015186.pdf

Nonivamide is an organic compound and a capsaicinoid. It is an amide of pelargonic acid (n-nonanoic acid) and vanillyl amine. It is present in chili peppers, but is commonly manufactured synthetically. Nonivamide (trade name Finalgon ) is used in topical ointments and creams to relieve minor aches and pains of muscles and joints. Nonivamide is also available in large adhesive bandages that can be applied to the back. Concentrations are typically between 0.025% and 0.075%. Nonivamide is a TRPV1 ion channel agonist.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Fatty acid uptake 1 Target ID: Fatty acid uptake Sources: http://www.ncbi.nlm.nih.gov/pubmed/25422952	Inhibitor 8297	1.08 µM [IC50]
Acetyl-coenzyme A synthetase 1 Target ID: CHEMBL2924 Sources: http://www.ncbi.nlm.nih.gov/pubmed/25422952	Activator 1430
Vanilloid receptor 53 Target ID: CHEMBL5102 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22796184	Agonist 2678	223.0 nM [EC50]
Vanilloid receptor 53 Target ID: CHEMBL4794 Sources: http://www.generon.co.uk/-0/nonivamide-pseudocapsaicin-pelargonic-231008642.html	Agonist 2678

Conditions

Condition	Modality	Targets	Highest Phase	Product
Low back pain 22 Sources: https://clinicaltrials.gov/ct2/show/NCT02300311	Palliative		Phase III 656	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
The taming of capsaicin. Reversal of the vanilloid activity of N-acylvanillamines by aromatic iodination.	2005 Jul 14	16000002
Localization of SSeCKS in unmyelinated primary sensory neurons.	2008 Mar 19	18353188
A comparison of pretreatment with a topical combination of nonivamide and nicoboxil and surgical delay in a random pattern skin flap model.	2009 Jul	18456588
Protective effect and relation structure-activity of nonivamide and iododerivatives in several models of lipid oxidation.	2009 Jul 15	19497416
Angiotensin-converting enzyme inhibitory and antioxidant activities of enzymatically synthesized phenolic and vitamin glycosides.	2009 Mar	18547170
N-vanillylnonanamide tested as a non-toxic antifoulant, applied to surfaces in a polyurethane coating.	2009 Sep	19488677
Capsaicinoids, chloropicrin and sulfur mustard: possibilities for exposure biomarkers.	2010	21833179
Contributions of TRPV1, endovanilloids, and endoplasmic reticulum stress in lung cell death in vitro and lung injury.	2012 Jan 1	21949157
Transient receptor potential vanilloid-1 (TRPV1) is a mediator of lung toxicity for coal fly ash particulate material.	2012 Mar	22155782

Patents

Sample Use Guides

In Vivo Use Guide

No more than 5 mm should be used to cover an area the size of a hand.

Route of Administration: Topical

In Vitro Use Guide

Addition of 1 to 100 uM of nonivamide reduced fatty acid uptake in a dose-dependent manner in Caco-2 cells

Name

Type

Language

NONIVAMIDE

Official Name

English

VANILLYL PELARGONIC AMIDE

Systematic Name

English

N-VANILLYLNONANAMIDE

Systematic Name

English

PSEUDOCAPSAICIN

Common Name

English

NSC-172795

Code

English

NONIVAMIDE [MART.]

Common Name

English

N-VANILLYLNONAMIDE

Common Name

English

NONANOYL 4-HYDROXY-3-METHOXYBENZYLAMIDE

Systematic Name

English

HYDROXYMETHOXYBENZYL PELARGONAMIDE

Official Name

English

Nonivamide [WHO-DD]

Common Name

English

NONYLIC ACID VANILLYAMIDE

Common Name

English

AH-23491X

Code

English

N-NONANOYL-4-HYDROXY-3-METHOXYBENZYL-AMIDE [FHFI]

Common Name

English

PELARGONIC ACID VANILLYLAMIDE

Systematic Name

English

NONIVAMIDE (CONSTITUENT OF CAPSICUM) [DSC]

Common Name

English

HANSAPLAST

Brand Name

English

HYDROXYMETHOXYBENZYL PELARGONAMIDE [INCI]

Common Name

English

FEMA NO. 2787

Code

English

nonivamide [INN]

Common Name

English

VANILLYL N-NONYLAMIDE

Systematic Name

English

VANILLYL-N-NONYLAMIDE

Systematic Name

English

Classification Tree Code System Code

EPA PESTICIDE CODE

70709