An endogenous fatty acid amide
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Stearda

Item No. 38973

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-[2-(3,4-dihydroxyphenyl)ethyl]-octadecanamide
CAS Number
105955-10-0
Synonyms
  • N-octadecanoyl Dopamine
  • N-Stearoyl Dopamine
Molecular Formula
C26H45NO3
Formula Weight
419.6
Purity
≥95%
Formulation
A solid
Solubility(Learn about Variance in Solubility)
Chloroform: Slightly solubleDMSO: SolubleMethanol: Slightly soluble
SMILES
O=C(CCCCCCCCCCCCCCCCC)NCCC1=CC=C(C(O)=C1)O
InChi Code
InChI=1S/C26H45NO3/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/h18-19,22,28-29H,2-17,20-21H2,1H3,(H,27,30)
InChi Key
KOCSVLPLQCBIGW-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    10 mg

    $72

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    50 mg

    $323

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    100 mg

    $572

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    250 mg

    $1,073

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    Product Description

    Stearda is an endogenous fatty acid amide composed of the catecholamine dopamine (Item Nos. 36532 | 21992) conjugated to the long-chain saturated fatty acid stearic acid (Item No. 10011298).1 It is an inhibitor of 5-lipoxygenase (5-LO; IC50 = 16 nM). Stearda is cytotoxic to K562 chronic myeloid leukemia cells, HOS osteosarcoma fibroblasts, and IMR-32 neuroblastoma cells but not MCF-7 breast cancer cells (IC50s = 36.8, 15, 1.5, and >100 µM, respectively).2 It potentiates calcium influx induced by the arachidonoyl amino acid and cannabinoid 1 (CB1) receptor agonist N-arachidonoyl dopamine (NADA; Item No. 90057) in HEK293 cells expressing human transient receptor potential vanilloid 6 (TRPV6) when used at concentrations of 1 or 10 µM.3 In vivo, stearda (0.1 mg/ml per paw), in combination with NADA, decreases latency to paw withdrawal in the hot plate test in rats.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. 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).

    2. Akimov, M., Gretskaya, N.M., Zinchenko, G.N., et al. Cytotoxicity of endogenous lipids N-acyl dopamines and their possible metabolic derivatives for human cancer cell lines of different histological origin. Anticancer Res. 35(5), 2657-2662 (2015).

    3. De Petrocellis, L., Chu, C.J., Moriello, A.S., et al. Actions of two naturally occurring saturated N-acyldopamines on transient receptor potential vanilloid 1 (TRPV1) channels. Br. J. Pharmacol. 143(2), 251-256 (2004).