Nonivamide

Names

[ Name ]:
Nonivamide

[Synonym ]:
N-[(4-hydroxy-3-methoxy-phenyl)methyl]nonanamide
Nonanimidic acid, N-[(4-hydroxy-3-methoxyphenyl)methyl]-, (1Z)-
N-vanillyl-nonanamide
Vanillyl pelargonic amide
(N-(4-Hydroxy-3-methoxybenzyl)nonanamide
Nonivamide
Vanillyl-N-nonylamide
Pseudocapsaicin
Capsaicin (Synthetic)
N-VANILLYLNONANOAMIDE
Nonanamide, N-vanillyl-
Pelargonyl vanillylamide
N-Nonylvanylamide
NonvaMide
Capsaicin std.
nonanoic acid vanillylamide
EINECS 219-484-1
N-(4-Hydroxy-3-methoxybenzyl)nonanamide
Capsaicinoid
N-Pelargonic Acid Vanillylamide
MFCD00017286
Capsaicin synthetic
Pelargonic acid vanillylamide
NONYLVANYLAMIDE
N-Pelargonylvanillylamide
N-Vanillylnonanamide
Vanillyl n-nonoylamide
nonylic acid vanillylamide
PAVA
NON-4-ENE
(1Z)-N-(4-Hydroxy-3-methoxybenzyl)nonanimidic acid
Nonanamide, N-[(4-hydroxy-3-methoxyphenyl)methyl]-
N-Vanillylpelargonamide
N-Vanillyl nonan amide

Biological Activity

[Description]:

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

[Related Catalog]:

Signaling Pathways >> Membrane Transporter/Ion Channel >> TRP Channel

Natural Products >> Alkaloid

Research Areas >> Neurological Disease

[Target]

TRPV1[1]

[In Vitro]

Nonivamide, a synthetic derivate of natural capsaicin, has an effective antifouling activity. Capsaicin exhibits 4d-EC50 values of 5.5±0.5 mg/L, 23±2 mg/L, 6.9±0.2 mg/L, and 15.6±0.4 mg/L in static toxicity tests conducted using Pseudomonas putida, Lake Erie bacteria, Vibrio natriegens, and Vibrio parahaemolyticus, respectively. A significant growth inhibitory effect (p<0.01) is observed in the group treated with 1 mg/L of Nonivamide for 4 d, and the EC50 value (4 d-EC50) is 5.1 mg/L[1]. Nonivamide treatment causes calcium release from the ER and altered the transcription of growth arrest- and DNA damage-inducible transcript 3 (GADD153), GADD45α, GRP78/BiP, ATF3, CCND1, and CCNG2) in a manner comparable with prototypical ER stress-inducing agents. ER calcium flux is evaluated by pretreating cells with 2.5 μM thapsigargin for 5 min followed by addition of 2.5 μM Nonivamide. Treatment of TRPV1-overexpressing cells with 2.5 μM Nonivamide produces marked increases in cytosolic calcium due to release of calcium from ER stores. Treatment of TRPV1-overexpressing cells with 1 μM Nonivamide causes an approximate 50% loss in cell viability after a 24-h period. BEAS-2B cells treated with 100 and 200 μM Nonivamide also exhibits a shift in the relative amount of EIF2α-P and an increase in the expression of GADD153 mRNA and protein[2]. Treatment with Nonivamide reduces lipid accumulation to a similar extent as CAP; the effects are not different from the effects after CAP treatment at any of the tested concentrations. Compared to untreated control cells, treatment with Nonivamide decreases lipid accumulation by 5.34±1.03% (P<0.05) at 0.01 µM up to 10.4±2.47% (P<0.001) at 1 µM[3].

[Cell Assay]

In the MTT assay, the reduction of yellow tetrazolium salt MTT to a purple formazan by mitochondrial and ER enzymes is used as a measure for cell viability. Cells are seeded in 96‐well plates and treated with 1 nM-10 µM CAP or Nonivamide with or without addition of 25-100 µM BCH or the corresponding ethanol concentration (0.1-0.2% (v/v), solvent control) for 12 days after initiation of differentiation. Cell culture media is exchanged every second day. On Day 12, 100 µL of the MTT working reagent (0.83 mg/mL MTT diluted in PBS/serum-free media (1:5)), is added to each well, and cells are incubated at 37°C for approximately 15 min. The MTT working solution is removed and the purple formazan formed during incubation is dissolved in 150 µL DMSO per well. Absorbance is measured at 550 nm with 690 nm as reference wavelength using multiwell plate reader. The number of metabolically active cells is calculated relative to untreated control cells or the corresponding solvent control (100%)[3].

[References]

[1]. Zhou J, et al. Toxic effects of environment-friendly antifoulant Nonivamide on Phaeodactylum tricornutum. Environ Toxicol Chem. 2013 Apr;32(4):802-9.

[2]. Thomas KC, et al. 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.

[3]. Rohm B, et al. Nonivamide enhances miRNA let-7d expression and decreases adipogenesis PPARγ expression in 3T3-L1 cells. J Cell Biochem. 2015 Jun;116(6):1153-63.

[Related Small Molecules]

capsaicin | Capsazepine | EIPA | Diphenyleneiodonium chloride | HC-030031 | SKF-96365 | HC 067047 | AMG 9810 | GSK-1016790A | SAR7334 | PF-4840154 | RN-1734 | AMG-517 | SB-366791 | IcilinAG-3-5

Chemical & Physical Properties

[ Density]:
1.0±0.1 g/cm3

[ Boiling Point ]:
450.4±55.0 °C at 760 mmHg

[ Melting Point ]:
54°C

[ Molecular Formula ]:
C₁₇H₂₇NO₃

[ Molecular Weight ]:
293.401

[ Flash Point ]:
226.2±31.5 °C

[ Exact Mass ]:
293.199097

[ PSA ]:
58.56000

[ LogP ]:
4.38

[ Vapour Pressure ]:
0.0±1.2 mmHg at 25°C

[ Index of Refraction ]:
1.509

[ Storage condition ]:
2-8°C

[ Stability ]:
Stable. Incompatible with strong oxidizing agents.

[ Water Solubility ]:
methanol: 100 mg/mL, clear to slightly hazy

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: RA5955000

CHEMICAL NAME :: Nonanamide, N-((4-hydroxy-3-methoxyphenyl)methyl)-

CAS REGISTRY NUMBER :: 2444-46-4

BEILSTEIN REFERENCE NO. :: 2144300

LAST UPDATED :: 199701

DATA ITEMS CITED :: 2

MOLECULAR FORMULA :: C17-H27-N-O3

MOLECULAR WEIGHT :: 293.45

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 8 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JMCMAR Journal of Medicinal Chemistry. (American Chemical Soc., Distribution Office Dept. 223, POB POB 57136, West End Stn., Washington, DC 20037) V.6- 1963- Volume(issue)/page/year: 36,2595,1993

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H315-H317-H319-H335

[ Precautionary Statements ]:
P261-P280-P305 + P351 + P338

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Faceshields;Gloves

[ Hazard Codes ]:
T:Toxic

[ Risk Phrases ]:
R25;R36/37/38

[ Safety Phrases ]:
S26-S45

[ RIDADR ]:
UN 3462 6.1/PG 2

[ WGK Germany ]:
3

[ RTECS ]:
RA5998000

[ Hazard Class ]:
6.1

[ HS Code ]:
2924299090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2924299090

[ Summary ]:
2924299090. other cyclic amides (including cyclic carbamates) and their derivatives; salts thereof. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0%

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