5-Methoxytryptophol (BioCAD00000019987)

blood cerebrospinal fluid (csf)

Metabolite Card

Formula: C11H13NO2 (191.0946)
SMILES: COC1=CC=C2NC=C(CCO)C2=C1

Synonyms [en]

5-methoxytryptophol; 5-methoxyindole-3-ethanol; methoxytryptophol; 5-Methoxy-1H-indole-3-ethanol; 2-(5-methoxy-1H-indol-3-yl)ethan-1-ol; 3-(2-Hydroxyethyl)-5-Methoxy-1H-indole

Reviewed

Last reviewed on 2024-06-28.

Cite this Page

5-Methoxytryptophol. 数据之源,洞见之始. SMRUCC genomics institute, a synthetic life researcher from China. https://biocad_registry.innovation.ac.cn/s/(-)-arctiin (retrieved 2026-01-03) (CAD Registry RN: BioCAD00000019987). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Note

5-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).

Entity Information

DBLinks

Other DBLinks
  • CAS Registry Number: 712-09-4
  • PubChem: 12835
  • ChEBI: ChEBI:114833
  • ChEBI: ChEBI:89851
  • HMDB: HMDB0001896
  • HMDB: HMDB01896
  • BioCyc: CPD-12021
  • NCBI MeSH: methoxytryptophol
  • Wikipedia: Tryptophol
  • RefMet: RM0108608
  • MoNA: FiehnHILIC000130
  • MoNA: HMDB0001896_ms_ms_1813
  • MoNA: HMDB0001896_ms_ms_1814
  • MoNA: HMDB0001896_ms_ms_1815
  • Metlin: METLIN_58062
  • Coconut NaturalProduct: CNP0209412.0

Class / Ontology

Metabolic Network
ID EC Number Name
BioCyc:RXN-11069 5-methoxyindoleacetaldehyde reductase
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Organism Source

Taxonomy Source

  1. Homo sapiens [ncbi taxid: 9606]

Pathway Synthetic

pathway id name
BioCyc:HUMAN_PWY66-401 superpathway of tryptophan utilization
BioCyc:HUMAN_PWY-6402 superpathway of melatonin degradation
BioCyc:META_PWY-6399 melatonin degradation II
BioCyc:HUMAN_PWY-6399 melatonin degradation II
BioCyc:META_PWY-6402 superpathway of melatonin degradation
View All Pathways