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 8504	1.08 µM [IC50]
Acetyl-coenzyme A synthetase 1 Target ID: CHEMBL2924 Sources: http://www.ncbi.nlm.nih.gov/pubmed/25422952	Activator 1447
Vanilloid receptor 53 Target ID: CHEMBL5102 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22796184	Agonist 2752	223.0 nM [EC50]
Vanilloid receptor 53 Target ID: CHEMBL4794 Sources: http://www.generon.co.uk/-0/nonivamide-pseudocapsaicin-pelargonic-231008642.html	Agonist 2752

Conditions

Condition	Modality	Targets	Highest Phase	Product
Low back pain 22 Sources: https://clinicaltrials.gov/ct2/show/NCT02300311	Palliative		Phase III 665	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Transient receptor potential vanilloid-1 (TRPV1) is a mediator of lung toxicity for coal fly ash particulate material.	2012-03	22155782
Contributions of TRPV1, endovanilloids, and endoplasmic reticulum stress in lung cell death in vitro and lung injury.	2012-01-01	21949157
Structure-activity relationship of capsaicin analogs and transient receptor potential vanilloid 1-mediated human lung epithelial cell toxicity.	2011-05	21343315
Capsaicinoids, chloropicrin and sulfur mustard: possibilities for exposure biomarkers.	2010	21833179
Synthesis, photolysis studies and in vitro photorelease of caged TRPV1 agonists and antagonists.	2009-11-21	19865707
N-vanillylnonanamide tested as a non-toxic antifoulant, applied to surfaces in a polyurethane coating.	2009-09	19488677
Protective effect and relation structure-activity of nonivamide and iododerivatives in several models of lipid oxidation.	2009-07-15	19497416
A comparison of pretreatment with a topical combination of nonivamide and nicoboxil and surgical delay in a random pattern skin flap model.	2009-07	18456588
Angiotensin-converting enzyme inhibitory and antioxidant activities of enzymatically synthesized phenolic and vitamin glycosides.	2009-03	18547170
Local translation in primary afferent fibers regulates nociception.	2008-04-09	18398477
Localization of SSeCKS in unmyelinated primary sensory neurons.	2008-03-19	18353188
Transdermal delivery of capsaicin derivative-sodium nonivamide acetate using microemulsions as vehicles.	2008-02-12	17766068
Neuroprotective effects of glyceryl nonivamide against microglia-like cells and 6-hydroxydopamine-induced neurotoxicity in SH-SY5Y human dopaminergic neuroblastoma cells.	2007-12	17855475
Evaluation of ketoprofen formulations via penetration rate and irritation in vivo study.	2007-07-18	17382500
Transient receptor potential vanilloid 1 agonists cause endoplasmic reticulum stress and cell death in human lung cells.	2007-06	17332266
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.	2007-04	17307377
Exploration of structure-antifouling relationships of capsaicin-like compounds that inhibit zebra mussel (Dreissena polymorpha) macrofouling.	2007	17852065
Hydrogen sulfide mediates hypoxia-induced relaxation of trout urinary bladder smooth muscle.	2006-08	16888071
Caged vanilloid ligands for activation of TRPV1 receptors by 1- and 2-photon excitation.	2006-04-18	16605259
Characteristics and actions of NAD(P)H oxidase on the sarcoplasmic reticulum of coronary artery smooth muscle.	2006-03	16227345
TRPV1 antagonists elevate cell surface populations of receptor protein and exacerbate TRPV1-mediated toxicities in human lung epithelial cells.	2006-01	16120755
Medical management of the traumatic consequences of civil unrest incidents: causation, clinical approaches, needs and advanced planning criteria.	2006	17192122
Analysis of eight capsaicinoids in peppers and pepper-containing foods by high-performance liquid chromatography and liquid chromatography-mass spectrometry.	2005-11-16	16277419
Assessment of pepper spray product potency in Asian and Caucasian forearm skin using transepidermal water loss, skin temperature and reflectance colorimetry.	2005-10-13	16220469
Electrically-assisted skin permeation of two synthetic capsaicin derivatives, sodium nonivamide acetate and sodium nonivamide propionate, via rate-controlling polyethylene membranes.	2005-09	16141542
Local heating of human skin by millimeter waves: effect of blood flow.	2005-09	15931684
The taming of capsaicin. Reversal of the vanilloid activity of N-acylvanillamines by aromatic iodination.	2005-07-14	16000002
Quantitative determination of capsaicinoids by liquid chromatography-electrospray mass spectrometry.	2005-04	15803309
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
Metabolism of capsaicin by cytochrome P450 produces novel dehydrogenated metabolites and decreases cytotoxicity to lung and liver cells.	2003-03	12641434
Improved dorsal random-pattern skin flap survival in rats with a topically applied combination of nonivamide and nicoboxil.	2003-03	12621192
Ceramide-induced activation of NADPH oxidase and endothelial dysfunction in small coronary arteries.	2003-02	12424096
Determination of capsaicin, nonivamide, and dihydrocapsaicin in blood and tissue by liquid chromatography-tandem mass spectrometry.	2002-09	12220011
In vitro topical application and in vivo pharmacodynamic evaluation of nonivamide hydrogels using Wistar rat as an animal model.	2002-06	12036718
Growth hormone inhibits apoptosis in in vitro produced bovine embryos.	2002-02	11803552
In vitro and in vivo evaluations of topically applied capsaicin and nonivamide from hydrogels.	2001-08-14	11472818
Evaluation of percutaneous absorption and skin irritation of ketoprofen through rat skin: in vitro and in vivo study.	2001-07-17	11427353
Quantitative analysis of capsaicinoids in fresh peppers, oleoresin capsicum and pepper spray products.	2001-05	11372985
Biphasic membrane effects of capsaicin, an active component in Capsicum species.	2001-05	11297867
Determination of capsaicin, dihydrocapsaicin, and nonivamide in self-defense weapons by liquid chromatography-mass spectrometry and liquid chromatography-tandem mass spectrometry.	2001-04-06	11330795
Kinetics of finite dose absorption through skin 1. Vanillylnonanamide.	2001-02	11169537
Capsaicin and nonivamide as novel skin permeation enhancers for indomethacin.	2001-01	11113638

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 `Mon Mar 31 19:28:06 GMT 2025` Edited by `admin` on `Mon Mar 31 19:28:06 GMT 2025`
Record UNII	S846B891OR
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NONIVAMIDE

Official Name

English

HYDROXYMETHOXYBENZYL PELARGONAMIDE

Preferred 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

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

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