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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-03-08 14:40:32 UTC
Update Date2019-01-11 19:16:19 UTC
HMDB IDHMDB0001896
Secondary Accession Numbers
  • HMDB01896
Metabolite Identification
Common Name5-Methoxytryptophol
Description5-Methoxytryptophol is synthesized by the pineal gland. Daily rhythms in pineal methoxyindole metabolism have been described in rodents and humans (5-Methoxytryptophol levels are coincident with serotonin levels in rodents pineal) and 5-Methoxytryptophol at its highest during the daylight hours and fall markedly soon after the onset of darkness, coincident with increases in the levels of pineal melatonin and the activities of pineal serotonin-N-acetyltransferase (EC 2.3.1.87, SNAT) and hydroxyindole-O-methyltransferase (EC 2.1.1.4, HIOMT). The fact that the levels of 5-methoxytryptophol and melatonin vary in parallel suggests that the major factor generating the methoxyindole rhythms is not SNAT activity, but perhaps a change in the availability (for metabolism) of "stored" serotonin. When the onset of darkness is delayed by 12 hours, human 5-methoxytryptophol (and melatonin) rhythms usually require 3 or 4 days to adjust to the new lighting regimen. Environmental factors, other than light, that activate the sympathetic nervous system or cause epinephrine to be secreted from the adrenal medulla (e.g., the stress of immobilization; insulin-induced hypoglycemia) can override the inhibitory effects of light and accelerate melatonin synthesis. Rhythms in 5-methoxytryptophol (and melatonin) synthesis apparently persist among animals placed in environments of continuous darkness; the source of the cyclic signal (mediated by the pineal sympathetic nerves) has not yet been identified. Preliminary evidence suggests that levels of a peptide hormone, arginine vasotocin, in rat pineal and sera also exhibit daily rhythms and are increased by norepinephrine. The circadian rhythm of melatonin secretion is generated in the suprachiasmatic nucleus. Sleep disruption, nightly restlessness, sundowning, and other circadian disturbances are frequently seen in Alzheimer's disease patients. Changes in the suprachiasmatic nucleus and pineal gland are thought to be the biological basis for these behavioral disturbances. (PMID 288858 , 2245336 ).
Structure
Data?1547234179
Synonyms
ValueSource
5-Methoxy-1H-indole-3-ethanolHMDB
5-Methoxyindole-3-ethanolHMDB
MethoxytryptopholHMDB
5-MethoxytryptopholMeSH
Chemical FormulaC11H13NO2
Average Molecular Weight191.2264
Monoisotopic Molecular Weight191.094628665
IUPAC Name2-(5-methoxy-1H-indol-3-yl)ethan-1-ol
Traditional Namemethoxytryptophol
CAS Registry Number712-09-4
SMILES
COC1=CC=C2NC=C(CCO)C2=C1
InChI Identifier
InChI=1S/C11H13NO2/c1-14-9-2-3-11-10(6-9)8(4-5-13)7-12-11/h2-3,6-7,12-13H,4-5H2,1H3
InChI KeyQLWKTGDEPLRFAT-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 3-alkylindoles. 3-alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassIndoles
Direct Parent3-alkylindoles
Alternative Parents
Substituents
  • 3-alkylindole
  • Anisole
  • Alkyl aryl ether
  • Substituted pyrrole
  • Benzenoid
  • Pyrrole
  • Heteroaromatic compound
  • Ether
  • Azacycle
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Alcohol
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Biological location:

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.64 g/LALOGPS
logP1.84ALOGPS
logP1.44ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)15.83ChemAxon
pKa (Strongest Basic)-2.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area45.25 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity55.18 m³·mol⁻¹ChemAxon
Polarizability20.86 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03dj-0900000000-56fc4171bff27cc8b08fJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00dj-4290000000-b6f1d2b77bcf63cdb2f6JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-006x-0900000000-8a87d83f5ab6d4e9e2ccJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-053r-0900000000-c2439fe463c8095a7d48JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-001i-0900000000-8eaf28224968f5678d87JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00dl-0900000000-1daafd240067b254f72cJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0900000000-f1948c2696d6933b1288JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00l7-0900000000-e7c232e2fb6c1faceb85JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-f761824cdb02ac2006c9JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ox-0900000000-10aea01d485547bbcdbaJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-0900000000-f47925a67fbbcd379d7cJSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.00009 +/- 0.000016 uMAdolescent (13-18 years old)MaleNormal details
BloodDetected and Quantified0.00009 +/- 0.000016 uMChildren (1-13 years old)FemaleNormal details
BloodDetected and Quantified0.00015 +/- 0.00002 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.00016 +/- 0.00003 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.00014 +/- 0.00001 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.00017 +/- 0.00003 uMAdult (>18 years old)MaleNormal details
BloodDetected and Quantified0.00014 +/- 0.000016 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.000058 +/- 0.00001 uMChildren (1-13 years old)MaleNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Cerebrospinal Fluid (CSF)Detected and Quantified0.03 +/- 0.22 (0.004 - 0.04) uMChildren (1-13 years old)BothLeukemia details
Cerebrospinal Fluid (CSF)Detected and Quantified0.02 +/- 0.022 (0 - 0.07) uMAdult (>18 years old)BothNeurological disorders (2 - 18 years old) details
Associated Disorders and Diseases
Disease References
Leukemia
  1. Curtius HC, Wolfensberger M, Redweik U, Leimbacher W, Maibach RA, Isler W: Mass fragmentography of 5-hydroxytryptophol and 5-methoxytryptophol in human cerebrospinal fluid. J Chromatogr. 1975 Oct 29;112:523-31. [PubMed:1184685 ]
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022726
KNApSAcK IDNot Available
Chemspider ID12305
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTryptophol
METLIN IDNot Available
PubChem Compound12835
PDB IDNot Available
ChEBI ID114833
References
Synthesis ReferenceTaborsky, Robert G.; Delvigs, Peter. Synthesis of some substituted tryptophols of possible physiological importance and a study with 3-(2-acetoxyethyl)-5-methoxyindole (5-methoxytryptophol O-acetate) on sexual maturation. J. Med. Chem., 1966, 9 (2), pp 251–254 DOI: 10.1021/jm00320a028
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Wurtman RJ, Ozaki Y: Physiological control of melatonin synthesis and secretion: mechanisms, generating rhythms in melatonin, methoxytryptophol, and arginine vasotocin levels and effects on the pineal of endogenous catecholamines, the estrous cycle, and environmental lighting. J Neural Transm Suppl. 1978;(13):59-70. [PubMed:288858 ]
  2. Curtius HC, Wolfensberger M, Redweik U, Leimbacher W, Maibach RA, Isler W: Mass fragmentography of 5-hydroxytryptophol and 5-methoxytryptophol in human cerebrospinal fluid. J Chromatogr. 1975 Oct 29;112:523-31. [PubMed:1184685 ]
  3. Skene DJ, Vivien-Roels B, Sparks DL, Hunsaker JC, Pevet P, Ravid D, Swaab DF: Daily variation in the concentration of melatonin and 5-methoxytryptophol in the human pineal gland: effect of age and Alzheimer's disease. Brain Res. 1990 Sep 24;528(1):170-4. [PubMed:2245336 ]