A TRPV1 agonist
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Isomer(s)
33407Nordihydrocapsaicin
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Nonivamide

Item No. 25328

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-[(4-hydroxy-3-methoxyphenyl)methyl]nonanamide
CAS Number
2444-46-4
Synonyms
  • Nonanoic Acid Vanillylamide
  • NSC 172795
  • Pelargonic Acid Vanillylamide
  • Pseudocapsaicin
  • N-Vanillylnonanamide
  • N-Vanillylpelargonamide
Molecular Formula
C17H27NO3
Formula Weight
293.4
Purity
≥95%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
0.1 M Na2CO3: 1 mg/mlDMF: 15 mg/mlDMSO: 13 mg/mlEthanol: 31 mg/ml
λmax
228 nm
SMILES
COC1=C(O)C=CC(CNC(CCCCCCCC)=O)=C1
InChi Code
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)
InChi Key
RGOVYLWUIBMPGK-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 g

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    Product Description

    Nonivamide is a transient receptor potential vanilloid type 1 (TRPV1) agonist and an analog of capsaicin (Item Nos. 92350 | 10010743) that has been isolated from Capsicum species.1,2 It is toxic to NHBE, BEAS-2B, and BEAS-2B cells overexpressing TRPV1 (TRPV1-OE; LC50s = 160, 115, and 1 µM, respectively), increases calcium flux in TRPV1-OE cells (EC50 = 1.4 µM), and increases GADD153 mRNA expression by 7- and 6-fold when used at concentrations of 2 and 20 µM, respectively.2 Nonivamide (1 µM) also increases the release of dopamine and serotonin from SH-SY5Y cells in a calcium-dependent and TRPV1-independent manner.3 In mice, it reduces respiration when inhaled and is toxic with LD50 values of 200 and 413 mg/kg for oral and inhaled administration, respectively.4 Formulations containing nonivamide have been used in pepper spray weaponry for riot control.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Constant, H.L., and Cordell, G.A. Nonivamide, a constituent of Capsicum oleoresin. J. Nat. Prod. 59(4), 425-426 (1996).

    2. Thomas, K.C., Ethirajan, M., Shahrokh, K., et al. Structure-activity relationship of capsaicin analogs and transient receptor potential vanilloid 1-mediated human lung epithelial cell toxicity. J. Pharmacol. Exp. Ther. 337(2), 400-410 (2011).

    3. Rohm, B., Holik, A.-K., Somoza, M.M., et al. Nonivamide, a capsaicin analog, increases dopamine and serotonin release in SH-SY5Y cells via a TRPV1-independent pathway. Mol. Nutr. Food Res. 57(11), 2008-2018 (2013).

    4. Satpute, R.M., Kushwaha, P.K., Nagar, D.P., et al. Comparative safety evaluation of riot control agents of synthetic and natural origin. Inhal. Toxicol. 30(2), 89-97 (2018).