6-Hydroxymelatonin

6-Hydroxymelatonin
Names

IUPAC name N-[2-(6-Hydroxy-5-methoxy-1H-indol-3-yl)ethyl]acetamide
Other names 6-Oxymelatonin
Identifiers
CAS Number	2208-41-5
3D model (Jmol)	Interactive image
ChEBI	CHEBI:198
ChemSpider	1794
ECHA InfoCard	100.164.426
KEGG	C05643
PubChem	1864
InChI 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) Key: OMYMRCXOJJZYKE-UHFFFAOYSA-N InChI=1/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) Key: OMYMRCXOJJZYKE-UHFFFAOYAK
SMILES CC(=O)NCCC1=CNC2=CC(=C(C=C21)OC)O
Properties
Chemical formula	C₁₃H₁₆N₂O₃
Molar mass	248.28 g·mol⁻¹
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

6-Hydroxymelatonin (6-OHM) is a naturally-occurring, endogenous, major active metabolite of the neurotransmitter melatonin.^[1] Similar to melatonin, 6-OHM is a full agonist of the MT₁ and MT₂ receptors.^[2]^[3] It is also an antioxidant and neuroprotective, and is even more potent in this regard relative to melatonin.^[4]^[5]

References

↑ Hardeland R (2010). "Melatonin metabolism in the central nervous system". Curr Neuropharmacol. 8 (3): 168–81. doi:10.2174/157015910792246244. PMC 3001211. PMID 21358968.
↑ Dubocovich ML (1988). "Pharmacology and function of melatonin receptors". FASEB J. 2 (12): 2765–73. PMID 2842214.
↑ Browning, Christopher; Beresford, Isabel; Fraser, Neil; Giles, Heather (2000). "Pharmacological characterization of human recombinant melatonin mt1and MT2receptors". British Journal of Pharmacology. 129 (5): 877–886. doi:10.1038/sj.bjp.0703130. ISSN 0007-1188. PMC 1571913. PMID 10696085.
↑ Maharaj DS, Glass BD, Daya S (2007). "Melatonin: new places in therapy". Biosci. Rep. 27 (6): 299–320. doi:10.1007/s10540-007-9052-1. PMID 17828452.
↑ Álvarez-Diduk R, Galano A, Tan DX, Reiter RJ (2015). "N-Acetylserotonin and 6-Hydroxymelatonin against Oxidative Stress: Implications for the Overall Protection Exerted by Melatonin". J Phys Chem B. 119: 8535–43. doi:10.1021/acs.jpcb.5b04920. PMID 26079042.

Neurotransmitters

Amino acid-derived	Major excitatory/inhibitory systems: Glutamate system: Agmatine Aspartic acid (aspartate) Cycloserine Glutamic acid (glutamate) Glutathione Glycine GSNO GSSG Kynurenic acid NAA NAAG Proline Serine; GABA system: GABA GABOB GHB; Glycine system: α-Alanine β-Alanine Glycine Hypotaurine Proline Sarcosine Serine Taurine; GHB system: GHB T-HCA (GHC) Biogenic amines: Monoamines: 6-OHM Dopamine Epinephrine (adrenaline) NAS (normelatonin) Norepinephrine (noradrenaline) Serotonin (5-HT); Trace amines: 3-Iodothyronamine N-Methylphenethylamine N-Methyltryptamine m-Octopamine p-Octopamine Phenylethanolamine Phenethylamine Synephrine Tryptamine m-Tyramine p-Tyramine; Others: Histamine Neuropeptides: See here instead.

Lipid-derived	Endocannabinoids: 2-AG 2-AGE (noladin ether) 2-ALPI 2-OG AA-5-HT Anandamide (AEA) DEA LPI NADA NAGly OEA Oleamide PEA RVD-Hpα SEA Virodhamine (O-AEA) Neurosteroids: See here instead.

Nucleobase-derived	Nucleosides: Adenosine system: Adenosine ADP AMP ATP

Vitamin-derived	Cholinergic system: Acetylcholine

Miscellaneous	Gasotransmitters: Carbon monoxide (CO) Hydrogen sulfide (H₂S) Nitric oxide (NO); Candidates: Acetaldehyde Ammonia (NH₃) Carbonyl sulfide (COS) Nitrous oxide (N₂O) Sulfur dioxide (SO₂)

Antioxidants

Food antioxidants	6-Hydroxymelatonin Acetyl-L-carnitine (ALCAR) Alpha-lipoic acid (ALA) Ascorbic acid (vitamin C) Carotenoids (vitamin A) Curcumin Edaravone Polyphenols Glutathione Hydroxytyrosol L-carnitine Ladostigil Melatonin Mofegiline N-Acetylcysteine (NAC) N-Acetylserotonin (NAS) Oleocanthal Oleuropein Rasagiline Resveratrol Selegiline Selenium Tocopherols (vitamin E) Tocotrienols (vitamin E) Tyrosol Ubiquinone (coenzyme Q) Uric acid

Fuel antioxidants	Butylated hydroxytoluene 2,6-Di-tert-butylphenol 1,2-Diaminopropane 2,4-Dimethyl-6-tert-butylphenol Ethylenediamine

Measurements	Folin method ORAC TEAC FRAP

Melatonin receptor modulators

MTR	Agonists: 2-Iodomelatonin 2-Phenylmelatonin 5-Methoxyluzindole 6-Chloromelatonin 6-Fluoromelatonin 6-Hydroxymelatonin 6-Methoxymelatonin 6,7-Dichloro-2-methylmelatonin 8-M-PDOT Agomelatine AMMTC GR-135,531 (of MT₃) GR-196,429 Melatonin N-Acetylserotonin (normelatonin) N-Acetyltryptamine N-Butanoylmelatonin N-Propionylmelatonin Piromelatine Ramelteon S-24268 S-25150 Tasimelteon TIK-301 (LY-156,735) Antagonists: 4-P-ADOT 4-P-PDOT Afobazole DH-97 Luzindole N-Acetyltryptamine (of MT₃) Prazosin (of MT₃) S-20928 S-22153 S-24601 S-25567 S-26131

See also: Adrenergics Dopaminergics Serotonergics Monoamine reuptake and release modulators Monoamine metabolism modulators Monoamine neurotoxins

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