Nonivamide | CAS#2444-46-4 | anti-inflammatory

MedKoo Cat#: 584875 | Name: Nonivamide

Featured

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Nonivamide is a capsaicin analogue that exhibits anti-inflammatory properties in peripheral blood mononuclear cells and U-937 macrophages.

Chemical Structure

Nonivamide

CAS#2444-46-4

Theoretical Analysis

MedKoo Cat#: 584875

Name: Nonivamide

CAS#: 2444-46-4

Chemical Formula: C17H25NO4

Exact Mass: 307.1784

Molecular Weight: 307.39

Elemental Analysis: C, 66.43; H, 8.20; N, 4.56; O, 20.82

Price and Availability

Size	Price	Availability	Quantity
1g	USD 235.00
10g	USD 440.00

Bulk Inquiry

Buy Now

Add to Cart

Related CAS #

No Data

Synonym

Nonivamide

IUPAC/Chemical Name

Benzamide, 4-hydroxy-3-methoxy-N-(1-oxononyl)-

InChi Key

FNBNWGZSHKLXGF-UHFFFAOYSA-N

InChi Code

InChI=1S/C17H25NO4/c1-3-4-5-6-7-8-9-16(20)18-17(21)13-10-11-14(19)15(12-13)22-2/h10-12,19H,3-9H2,1-2H3,(H,18,20,21)

SMILES Code

O=C(NC(CCCCCCCC)=O)C1=CC=C(O)C(OC)=C1

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Nonivamide is a agonist, which exhibits 4d-EC50 value of 5.1 mg/L.

In vitro activity:

This study shows that activation of the intracellular subpopulation of TRPV1 causes endoplasmic reticulum (ER) stress and cell death in human bronchial epithelial and alveolar cells. TRPV1 agonist (nonivamide) treatment caused calcium release from the ER and altered the transcription of growth arrest- and DNA damage-inducible transcript 3 (GADD153), GADD45alpha, GRP78/BiP, ATF3, CCND1, and CCNG2) in a manner comparable with prototypical ER stress-inducing agents. Reference: J Pharmacol Exp Ther. 2007 Jun;321(3):830-8. https://pubmed.ncbi.nlm.nih.gov/17332266/

In vivo activity:

This study investigated the effects of nonivamide (pelargonic acid vanillylamide, PAVA; 1 mg/kg) and rosuvastatin (RSV; 10 mg/kg) on hepatic steatosis induced by a high-fat diet (HFD). Male Sprague-Dawley rats were fed a HFD for 16 weeks then received PAVA or RSV for 4 additional weeks. Metabolic dysfunction and hepatic injury were reduced by RSV and PAVA treatment. PAVA regulated lipid deposition, improved insulin resistance, and decreased oxidative stress and apoptotic cell death. Reference: J Pharmacol Sci. 2020 Jul;143(3):188-198. https://pubmed.ncbi.nlm.nih.gov/32414691/

	Solvent	mg/mL	mM
Solubility
	DMF	15.0	48.80
	DMSO	57.0	185.43
	Ethanol	39.5	128.50

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 307.39 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Rohm B, Holik AK, Kretschy N, Somoza MM, Ley JP, Widder S, Krammer GE, Marko D, Somoza V. Nonivamide enhances miRNA let-7d expression and decreases adipogenesis PPARγ expression in 3T3-L1 cells. J Cell Biochem. 2015 Jun;116(6):1153-63. doi: 10.1002/jcb.25052. PMID: 25704235; PMCID: PMC4949678. 2. Thomas KC, Sabnis AS, Johansen ME, Lanza DL, Moos PJ, Yost GS, Reilly CA. Transient receptor potential vanilloid 1 agonists cause endoplasmic reticulum stress and cell death in human lung cells. J Pharmacol Exp Ther. 2007 Jun;321(3):830-8. doi: 10.1124/jpet.107.119412. Epub 2007 Mar 1. PMID: 17332266. 3. Wikan N, Tocharus J, Oka C, Sivasinprasasn S, Chaichompoo W, Suksamrarn A, Tocharus C. The capsaicinoid nonivamide suppresses the inflammatory response and attenuates the progression of steatosis in a NAFLD-rat model. J Biochem Mol Toxicol. 2023 Mar;37(3):e23279. doi: 10.1002/jbt.23279. Epub 2022 Dec 21. PMID: 36541345. 4. Wikan N, Tocharus J, Sivasinprasasn S, Kongkaew A, Chaichompoo W, Suksamrarn A, Tocharus C. Capsaicinoid nonivamide improves nonalcoholic fatty liver disease in rats fed a high-fat diet. J Pharmacol Sci. 2020 Jul;143(3):188-198. doi: 10.1016/j.jphs.2020.03.008. Epub 2020 Apr 10. PMID: 32414691

In vitro protocol:

In vivo protocol:

1. Wikan N, Tocharus J, Oka C, Sivasinprasasn S, Chaichompoo W, Suksamrarn A, Tocharus C. The capsaicinoid nonivamide suppresses the inflammatory response and attenuates the progression of steatosis in a NAFLD-rat model. J Biochem Mol Toxicol. 2023 Mar;37(3):e23279. doi: 10.1002/jbt.23279. Epub 2022 Dec 21. PMID: 36541345. 2. Wikan N, Tocharus J, Sivasinprasasn S, Kongkaew A, Chaichompoo W, Suksamrarn A, Tocharus C. Capsaicinoid nonivamide improves nonalcoholic fatty liver disease in rats fed a high-fat diet. J Pharmacol Sci. 2020 Jul;143(3):188-198. doi: 10.1016/j.jphs.2020.03.008. Epub 2020 Apr 10. PMID: 32414691

1: Walker J, Ley JP, Schwerzler J, Lieder B, Beltran L, Ziemba PM, Hatt H, Hans J, Widder S, Krammer GE, Somoza V. Nonivamide, a capsaicin analogue, exhibits anti-inflammatory properties in peripheral blood mononuclear cells and U-937 macrophages. Mol Nutr Food Res. 2017 Feb;61(2). doi: 10.1002/mnfr.201600474. Epub 2016 Nov 15. PubMed PMID: 27666931. 2: Duan L, Peng H, Li G, Wang R, Chen Y. Utility of in vitro and in vivo systems for studying the permeability of capsaicin and nonivamide through different intestinal regions. Xenobiotica. 2018 Jun;48(6):541-545. doi: 10.1080/00498254.2017.1344790. Epub 2017 Jul 6. PubMed PMID: 28627264. 3: Moro C, Bass J, Scott AM, Canetti EFD. Enhancing capillary blood collection: The influence of nicotinic acid and nonivamide. J Clin Lab Anal. 2017 Nov;31(6). doi: 10.1002/jcla.22142. Epub 2017 Jan 19. PubMed PMID: 28102549. 4: Rohm B, Riedel A, Ley JP, Widder S, Krammer GE, Somoza V. Capsaicin, nonivamide and trans-pellitorine decrease free fatty acid uptake without TRPV1 activation and increase acetyl-coenzyme A synthetase activity in Caco-2 cells. Food Funct. 2015 Jan;6(1):173-85. doi: 10.1039/c4fo00435c. Epub 2014 Nov 25. PubMed PMID: 25422952. 5: Yeh JL, Lo YC, Wang Y, Chen IJ. Cardiovascular interactions of nonivamide, glyceryl nonivamide, capsaicin analogues, and substance P antagonist in rats. Brain Res Bull. 1993;30(5-6):641-8. PubMed PMID: 7681355. 6: Zinner C, Holmberg HC, Sperlich B. Topical application of cream containing nonivamide and nicoboxil does not enhance the performance of experienced cyclists during a 4-km time-trial. Eur J Appl Physiol. 2016 May;116(5):969-74. doi: 10.1007/s00421-016-3357-3. Epub 2016 Mar 22. PubMed PMID: 27002820. 7: Blahova Z, Holm JC, Weiser T, Richter E, Trampisch M, Akarachkova E. Nicoboxil/nonivamide cream effectively and safely reduces acute nonspecific low back pain - a randomized, placebo-controlled trial. J Pain Res. 2016 Dec 14;9:1221-1230. doi: 10.2147/JPR.S118329. eCollection 2016. PubMed PMID: 28008281; PubMed Central PMCID: PMC5167490. 8: Hochkogler CM, Lieder B, Rust P, Berry D, Meier SM, Pignitter M, Riva A, Leitinger A, Bruk A, Wagner S, Hans J, Widder S, Ley JP, Krammer GE, Somoza V. A 12-week intervention with nonivamide, a TRPV1 agonist, prevents a dietary-induced body fat gain and increases peripheral serotonin in moderately overweight subjects. Mol Nutr Food Res. 2017 May;61(5). doi: 10.1002/mnfr.201600731. Epub 2017 Feb 22. PubMed PMID: 28012242. 9: Warnecke JM, Wendt T, Winkler S, Schak M, Schiffer T, Kohl-Bareis M. Evaluation of changes in the haemoglobin of skin and muscle tissue of the calf, as induced by topical application of a nonivamide/nicoboxil cream. Can J Physiol Pharmacol. 2014 Feb;92(2):149-54. doi: 10.1139/cjpp-2013-0158. Epub 2013 Oct 21. PubMed PMID: 24502638. 10: Herrmann S, Daniels R, Lunter D. Methods for the determination of the substantivity of topical formulations. Pharm Dev Technol. 2017 Jun;22(4):487-491. doi: 10.3109/10837450.2015.1135346. Epub 2016 Jan 11. PubMed PMID: 26754018. 11: Rohm B, Holik AK, Somoza MM, Pignitter M, Zaunschirm M, Ley JP, Krammer GE, Somoza V. Nonivamide, a capsaicin analog, increases dopamine and serotonin release in SH-SY5Y cells via a TRPV1-independent pathway. Mol Nutr Food Res. 2013 Nov;57(11):2008-18. doi: 10.1002/mnfr.201200846. Epub 2013 Aug 9. PubMed PMID: 23929722. 12: Rohm B, Holik AK, Kretschy N, Somoza MM, Ley JP, Widder S, Krammer GE, Marko D, Somoza V. Nonivamide enhances miRNA let-7d expression and decreases adipogenesis PPARγ expression in 3T3-L1 cells. J Cell Biochem. 2015 Jun;116(6):1153-63. doi: 10.1002/jcb.25052. PubMed PMID: 25704235; PubMed Central PMCID: PMC4949678. 13: Heck R, Lukić MŽ, Savić SD, Daniels R, Lunter DJ. Ex vivo skin permeation and penetration of nonivamide from and in vivo skin tolerability of film-forming formulations containing porous silica. Eur J Pharm Sci. 2017 Aug 30;106:34-40. doi: 10.1016/j.ejps.2017.05.045. Epub 2017 May 22. PubMed PMID: 28546105. 14: Gaubitz M, Schiffer T, Holm C, Richter E, Pisternick-Ruf W, Weiser T. Efficacy and safety of nicoboxil/nonivamide ointment for the treatment of acute pain in the low back - A randomized, controlled trial. Eur J Pain. 2016 Feb;20(2):263-73. doi: 10.1002/ejp.719. Epub 2015 Apr 30. PubMed PMID: 25929250; PubMed Central PMCID: PMC5029595. 15: Wu PC, Fang JY, Huang YB, Tsai YH. Development and evaluation of transdermal patches of nonivamide and sodium nonivamide acetate. Pharmazie. 1997 Feb;52(2):135-8. PubMed PMID: 9122272. 16: Yeh JL, Chen IJ. Cardiovascular effects of nonivamide succinate. Gaoxiong Yi Xue Ke Xue Za Zhi. 1991 Apr;7(4):173-82. PubMed PMID: 2030524. 17: Hochkogler CM, Lieder B, Schachner D, Heiss E, Schröter A, Hans J, Ley JP, Krammer GE, Somoza V. Capsaicin and nonivamide similarly modulate outcome measures of mitochondrial energy metabolism in HepG2 and 3T3-L1 cells. Food Funct. 2018 Feb 21;9(2):1123-1132. doi: 10.1039/c7fo01626c. PubMed PMID: 29362767. 18: Zhou J, Yang C, Wang J, Sun P, Fan P, Tian K, Liu S, Xia C. Toxic effects of environment-friendly antifoulant nonivamide on Phaeodactylum tricornutum. Environ Toxicol Chem. 2013 Apr;32(4):802-9. doi: 10.1002/etc.2132. Epub 2013 Mar 1. PubMed PMID: 23341258. 19: Lunter DJ, Daniels R. New film forming emulsions containing Eudragit® NE and/or RS 30D for sustained dermal delivery of nonivamide. Eur J Pharm Biopharm. 2012 Oct;82(2):291-8. doi: 10.1016/j.ejpb.2012.06.010. Epub 2012 Jun 28. PubMed PMID: 22750130. 20: Hochkogler CM, Rohm B, Hojdar K, Pignitter M, Widder S, Ley JP, Krammer GE, Somoza V. The capsaicin analog nonivamide decreases total energy intake from a standardized breakfast and enhances plasma serotonin levels in moderately overweight men after administered in an oral glucose tolerance test: a randomized, crossover trial. Mol Nutr Food Res. 2014 Jun;58(6):1282-90. doi: 10.1002/mnfr.201300821. Epub 2014 Feb 7. PubMed PMID: 24753478.