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

Molecular Formula	C17H27NO3
Molecular Weight	293.4012
Charge	0
Count

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

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
Determination of capsaicin, dihydrocapsaicin, and nonivamide in self-defense weapons by liquid chromatography-mass spectrometry and liquid chromatography-tandem mass spectrometry.	2001 Apr 6	11330795
In vitro and in vivo evaluations of topically applied capsaicin and nonivamide from hydrogels.	2001 Aug 14	11472818
Kinetics of finite dose absorption through skin 1. Vanillylnonanamide.	2001 Feb	11169537
Capsaicin and nonivamide as novel skin permeation enhancers for indomethacin.	2001 Jan	11113638
Evaluation of percutaneous absorption and skin irritation of ketoprofen through rat skin: in vitro and in vivo study.	2001 Jul 17	11427353
Quantitative analysis of capsaicinoids in fresh peppers, oleoresin capsicum and pepper spray products.	2001 May	11372985
Biphasic membrane effects of capsaicin, an active component in Capsicum species.	2001 May	11297867
Metabolism of capsaicin by cytochrome P450 produces novel dehydrogenated metabolites and decreases cytotoxicity to lung and liver cells.	2003 Mar	12641434
A possible involvement of plasma membrane NAD(P)H oxidase in the switch mechanism of the cell death mode from apoptosis to necrosis in menadione-induced cell injury.	2004	15625573
The taming of capsaicin. Reversal of the vanilloid activity of N-acylvanillamines by aromatic iodination.	2005 Jul 14	16000002
Analysis of eight capsaicinoids in peppers and pepper-containing foods by high-performance liquid chromatography and liquid chromatography-mass spectrometry.	2005 Nov 16	16277419
Electrically-assisted skin permeation of two synthetic capsaicin derivatives, sodium nonivamide acetate and sodium nonivamide propionate, via rate-controlling polyethylene membranes.	2005 Sep	16141542
Local heating of human skin by millimeter waves: effect of blood flow.	2005 Sep	15931684
Medical management of the traumatic consequences of civil unrest incidents: causation, clinical approaches, needs and advanced planning criteria.	2006	17192122
Assessment of pepper spray product potency in Asian and Caucasian forearm skin using transepidermal water loss, skin temperature and reflectance colorimetry.	2006 Jan-Feb	16220469
Characteristics and actions of NAD(P)H oxidase on the sarcoplasmic reticulum of coronary artery smooth muscle.	2006 Mar	16227345
Exploration of structure-antifouling relationships of capsaicin-like compounds that inhibit zebra mussel (Dreissena polymorpha) macrofouling.	2007	17852065
Effect of topical application of capsaicin and its related compounds on dermal insulin-like growth factor-I levels in mice and on facial skin elasticity in humans.	2007 Apr	17307377
Neuroprotective effects of glyceryl nonivamide against microglia-like cells and 6-hydroxydopamine-induced neurotoxicity in SH-SY5Y human dopaminergic neuroblastoma cells.	2007 Dec	17855475
Evaluation of ketoprofen formulations via penetration rate and irritation in vivo study.	2007 Jul 18	17382500
Transient receptor potential vanilloid 1 agonists cause endoplasmic reticulum stress and cell death in human lung cells.	2007 Jun	17332266
Local translation in primary afferent fibers regulates nociception.	2008 Apr 9	18398477
Transdermal delivery of capsaicin derivative-sodium nonivamide acetate using microemulsions as vehicles.	2008 Feb 12	17766068
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
Synthesis, photolysis studies and in vitro photorelease of caged TRPV1 agonists and antagonists.	2009 Nov 21	19865707
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
Structure-activity relationship of capsaicin analogs and transient receptor potential vanilloid 1-mediated human lung epithelial cell toxicity.	2011 May	21343315
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

Substance Class	Chemical Created by `admin` on `Fri Dec 15 18:58:19 UTC 2023` Edited by `admin` on `Fri Dec 15 18:58:19 UTC 2023`
Record UNII	S846B891OR
Record Status	`Validated (UNII)`
Record Version

Download

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