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
Kinetics of finite dose absorption through skin 1. Vanillylnonanamide.	2001 Feb	11169537
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
Determination of capsaicin, nonivamide, and dihydrocapsaicin in blood and tissue by liquid chromatography-tandem mass spectrometry.	2002 Sep	12220011
Metabolism of capsaicin by cytochrome P450 produces novel dehydrogenated metabolites and decreases cytotoxicity to lung and liver cells.	2003 Mar	12641434
Improved dorsal random-pattern skin flap survival in rats with a topically applied combination of nonivamide and nicoboxil.	2003 Mar	12621192
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
Quantitative determination of capsaicinoids by liquid chromatography-electrospray mass spectrometry.	2005 Apr	15803309
The taming of capsaicin. Reversal of the vanilloid activity of N-acylvanillamines by aromatic iodination.	2005 Jul 14	16000002
Hydrogen sulfide mediates hypoxia-induced relaxation of trout urinary bladder smooth muscle.	2006 Aug	16888071
TRPV1 antagonists elevate cell surface populations of receptor protein and exacerbate TRPV1-mediated toxicities in human lung epithelial cells.	2006 Jan	16120755
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
Neuroprotective effects of glyceryl nonivamide against microglia-like cells and 6-hydroxydopamine-induced neurotoxicity in SH-SY5Y human dopaminergic neuroblastoma cells.	2007 Dec	17855475
Localization of SSeCKS in unmyelinated primary sensory neurons.	2008 Mar 19	18353188
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

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 GMT 2023` Edited by `admin` on `Fri Dec 15 18:58:19 GMT 2023`
Record UNII	S846B891OR
Record Status	`Validated (UNII)`
Record Version

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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