A synthetic endocannabinoid analog and potent 5-lipoxygenase inhibitor
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N-Oleoyl Dopamine

Item No. 10115

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-[2-(3,4-dihydroxyphenyl)ethyl]-9Z-octadecenamide
CAS Number
105955-11-1
Synonyms
  • ODA
Molecular Formula
C26H43NO3
Formula Weight
417.6
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 20 mg/mlEthanol: 50 mg/mlEthanol:PBS (pH 7.2) (1:1): 500 µg/ml
λmax
283 nm
SMILES
CCCCCCCC/C=C\CCCCCCCC(=O)NCCc1ccc(O)c(O)c1
InChi Code
InChI=1S/C26H43NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-26(30)27-21-20-23-18-19-24(28)25(29)22-23/h9-10,18-19,22,28-29H,2-8,11-17,20-21H2,1H3,(H,27,30)/b10-9-
InChi Key
QQBPLXNESPTPNU-KTKRTIGZSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

    $49

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    10 mg

    $93

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    50 mg

    $376

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    100 mg

    $655

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    Product Description

    N-Oleoyl dopamine (ODA) is a selective, endogenous vanilloid receptor 1 (VR1) agonist isolated from bovine brain.1 Structurally, it is the amide of oleic acid and dopamine and is therefore a “hybrid” analog which incorporates components of both the anandamide-like and dopamine neurotransmitter pathways. ODA binds to the human recombinant VR1 with a Ki of 36 nM making it equipotent to capsaicin and slightly more potent than N-arachidonoyl dopamine in this assay.1 It causes hyperalgesia and nocifensive behavior that is blocked by the VR1 antagonist iodo-resiniferatoxin. ODA is selective for VR1 based on observations that it has weak affinity for the rat CB1 receptor (Ki of 1.6 µM) and is a very weak inhibitor of FAAH. ODA is also a potent inhibitor of 5-lipoxygenase from rat basophilic leukemia-1 (RBL-1) cells, with a IC50 of 7.5 nM.2,3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Chu, C.J., Huang, S.M., De Petrocellis, L., et al. N-oleoyldopamine, a novel endogenous capsaicin-like lipid that produces hyperalgesia. The Journal of Biological Chemisty 278(16), 13633-13639 (2003).

    2. Tseng, C.F., Iwakami, S., Mikajiri, A., et al. Inhibition of in vitro prostaglandin and leukotriene biosyntheses by cinnamoyl-β-phenethylamine and N-acyldopamine derivatives. Chem. Pharm. Bull. (Tokyo) 40(2), 396-400 (1992).

    3. Iwakami, S., Shibuya, M., Tseng, C.F., et al. Inhibition of arachidonate 5-lipoxygenase by phenolic compounds. Chem. Pharm. Bull. (Tokyo) 34(9), 3960-3963 (1986).

    Product Citations

    Matsumoto, G., Inobe, T., Amano, T., et al. N-Acyldopamine induces aggresome formation without proteasome inhibition and enhances protein aggregation via p62/SQSTM1 expression. Sci. Rep. 8(1), 9585 (2018).