An arachidonoyl amino acid and CB1 receptor agonist
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Isomer(s)
90052Arvanil
Labeled Version(s)
10007431N-Arachidonoyl Dopamine-d8
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N-Arachidonoyl Dopamine

Item No. 90057

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-[2-(3,4-dihydroxyphenyl)ethyl]-5Z,8Z,11Z,14Z-eicosatetraenamide
CAS Number
199875-69-9
Synonyms
  • NADA
Molecular Formula
C28H41NO3
Formula Weight
439.6
Purity
≥98%
Formulation (Request formulation change)
A 50 mg/ml solution in ethanol
Solubility(Learn about Variance in Solubility)
0.1 M Na2CO3: Colloidal suspension @ <100 µgDMF: MiscibleDMSO: MiscibleEthanol: MiscibleEthanol:PBS (1:1): 100 µg/ml (colloidal suspensio
λmax
211, 284 nm
SMILES
CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)NCCc1ccc(O)c(O)c1
InChi Code
InChI=1S/C28H41NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-28(32)29-23-22-25-20-21-26(30)27(31)24-25/h6-7,9-10,12-13,15-16,20-21,24,30-31H,2-5,8,11,14,17-19,22-23H2,1H3,(H,29,32)/b7-6-,10-9-,13-12-,16-15-
InChi Key
MVVPIAAVGAWJNQ-DOFZRALJSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    5 mg

    $60

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    10 mg

    $108

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    50 mg

    $451

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    100 mg

    $708

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    Product Description

    N-Arachidonoyl dopamine (NADA) is an arachidonoyl amino acid and cannabinoid (CB) receptor 1 agonist (Ki = 250 nM in rat brain membranes, which highly express CB1 receptors).1 It is selective for CB1 over CB2 receptors (Ki = 12,000 nM in rat spleen membranes, which highly express CB2 receptors). NADA induces intracellular calcium mobilization in N18TG2 neuroblastoma cells (EC50 = 0.7 µM). It inhibits the proliferation of MCF-7 breast cancer cells (IC50 = 0.25 µM), an effect that can be reversed by the CB1 receptor antagonist SR141716A (rimonabant; Item No. 9000484). NADA (10 mg/kg) induces hypothermia, catalepsy, hypolocomotion, and analgesia in mice.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Bisogno, T., Melck, D., Bobrov, M.Y., et al. N-acyl-dopamines: Novel synthetic CB1 cannabinoid-receptor ligands and inhibitors of anandamide inactivation with cannabimimetic activity in vitro and in vivo. Biochem. J. 351(Pt 3), 817-824 (2001).

    Product Citations

    Kantae, V., Ogino, S., Noga, M., et al. Quantitative profiling of endocannabinoids and related N-acylethanolamines in human CSF using nano LC-MS/MS. J. Lipid. Res. 58(3), 615-624 (2017).

    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).