An active metabolite of melatonin
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6-hydroxy Melatonin

Item No. 21857

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-[2-(6-hydroxy-5-methoxy-1H-indol-3-yl)ethyl]-acetamide
CAS Number
2208-41-5
Synonyms
  • 6-OHM
Molecular Formula
C13H16N2O3
Formula Weight
248.3
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/mlDMSO:PBS (pH 7.2) (1:1): 0.5 mg/mlEthanol: 20 mg/ml
λmax
219, 303 nm
SMILES
COC1=C(O)C=C(NC=C2CCNC(C)=O)C2=C1
InChi Code
InChI=1S/C13H16N2O3/c1-8(16)14-4-3-9-7-15-11-6-12(17)13(18-2)5-10(9)11/h5-7,15,17H,3-4H2,1-2H3,(H,14,16)
InChi Key
OMYMRCXOJJZYKE-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    6-hydroxy Melatonin is an active metabolite of melatonin (Item No. 14427).1,2,3,4,5 It is formed from melatonin by the cytochrome P450 (CYP) isoform CYP1A2 in human liver microsomes.6 6-hydroxy Melatonin is a melatonin 1A (MT1A), MT1B, and MT2 receptor agonist.1,2 It inhibits dopamine release from isolated rabbit retina (IC50 = 0.0016 µM).3 6-hydroxy Melatonin (10 and 100 µM) reduces increases in the levels of NF-κB, IL-6, and IL-8 and decreases in glutathione (GSH) levels in LPS- and peptidoglycan G-stimulated human umbilical vein endothelial cells (HUVECs) in an in vitro model of sepsis.4 It reduces iron-induced lipid oxidation in rat hippocampal homogenate when administered at a dose of 10 mg/kg.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Dubocovich, M.L., Masana, M.I., Iacob, S., et al. Melatonin receptor antagonists that differentiate between the human Mel1a and Mel1b recombinant subtypes are used to assess the pharmacological profile of the rabbit retina ML1 presynaptic heteroreceptor. Naunyn-Schmiedeberg's Arch. Pharmacol. 355(3), 365-375 (1997).

    2. Dubocovich, M.L. Melatonin receptors: Are there multiple subtypes? Trends Pharamacol. Sci. 16(2), 50-56 (1995).

    3. Dubocovich, M.L. Characterization of a retinal melatonin receptor. J. Pharmacol. Exp. Ther. 234(2), 395-401 (1985).

    4. Lowes, D.A., Almawash, A.M., Webster, N.R., et al. Melatonin and structurally similar compounds have differing effects on inflammation and mitochondrial function in endothelial cells under conditions mimicking sepsis. Br. J. Anaesth. 107(2), 193-201 (2011).

    5. Maharaj, D.S., Maharaj, H., Daya, S., et al. Melatonin and 6-hydroxymelatonin protect against iron-induced neurotoxicity. J. Neurochem. 96(1), 78-81 (2006).

    6. Härtter, S., Wang, X., Weigmann, H., et al. Differential effects of fluvoxamine and other antidepressants on the biotransformation of melatonin. J. Clin. Psychopharmacol. 21(2), 167-174 (2001).