1.02011-09-21 00:18:32 UTC2015-10-09 22:32:40 UTCFDB0227265-Methoxytryptophol5-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) [HMDB]5-Methoxy-1H-indole-3-ethanol5-Methoxyindole-3-ethanol5-MethoxytryptopholMethoxytryptopholC11H13NO2191.2264191.0946286652-(5-methoxy-1H-indol-3-yl)ethan-1-olmethoxytryptophol712-09-4COC1=CC=C2NC=C(CCO)C2=C1InChI=1S/C11H13NO2/c1-14-9-2-3-11-10(6-9)8(4-5-13)7-12-11/h2-3,6-7,12-13H,4-5H2,1H3QLWKTGDEPLRFAT-UHFFFAOYSA-N 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.3-alkylindolesOrganic compoundsOrganoheterocyclic compoundsIndoles and derivativesIndolesAromatic heteropolycyclic compoundsAlkyl aryl ethersAnisolesAzacyclic compoundsHeteroaromatic compoundsHydrocarbon derivativesOrganonitrogen compoundsOrganopnictogen compoundsPrimary alcoholsSubstituted pyrroles3-alkylindoleAlcoholAlkyl aryl etherAnisoleAromatic heteropolycyclic compoundAzacycleBenzenoidEtherHeteroaromatic compoundHydrocarbon derivativeOrganic nitrogen compoundOrganic oxygen compoundOrganonitrogen compoundOrganooxygen compoundOrganopnictogen compoundPrimary alcoholPyrroleSubstituted pyrrolea small moleculeSolidlogp1.84logs-2.47solubility6.45e-01 g/llogp1.44pka_strongest_acidic15.83pka_strongest_basic-2.4iupac2-(5-methoxy-1H-indol-3-yl)ethan-1-olaverage_mass191.2264mono_mass191.094628665smilesCOC1=CC=C2NC=C(CCO)C2=C1formulaC11H13NO2inchiInChI=1S/C11H13NO2/c1-14-9-2-3-11-10(6-9)8(4-5-13)7-12-11/h2-3,6-7,12-13H,4-5H2,1H3inchikeyQLWKTGDEPLRFAT-UHFFFAOYSA-Npolar_surface_area45.25refractivity55.18polarizability20.86rotatable_bond_count3acceptor_count2donor_count2physiological_charge0formal_charge0Specdb::NmrOneD1789Specdb::NmrOneD166602Specdb::NmrTwoD1729Specdb::MsIr1457Specdb::MsIr1458Specdb::MsIr1459Specdb::CMs15406Specdb::CMs38175Specdb::CMs168181Specdb::MsMs1813Specdb::MsMs1814Specdb::MsMs1815Specdb::MsMs300142Specdb::MsMs300143Specdb::MsMs300144Specdb::MsMs342343Specdb::MsMs342344Specdb::MsMs342345Specdb::MsMs2277908Specdb::MsMs2277909Specdb::MsMs2277910Specdb::MsMs3087046Specdb::MsMs3087047Specdb::MsMs3087048HMDB01896#<Reference:0x00005556759c7a40>#<Reference:0x00005556759c7888>#<Reference:0x00005556759c76d0>AnatidaeType 1specificAnatidae8830BeefaloType 1specificBos taurus X Bison bison297284BisonType 1specificBison bison9901BuffaloType 1specificBubalus bubalis89462Cattle (Beef, Veal)Type 1specificBos taurus9913ChickenType 1specificGallus gallus9031Columbidae (Dove, Pigeon)Type 1specificColumbidae8930DeerType 1specificCervidae9850Domestic goatType 1specificCapra aegagrus hircus9925Domestic pigType 1specificSus scrofa domestica9825ElkType 1specificCervus canadensis1574408EmuType 1specificDromaius novaehollandiae8790European rabbitType 1specificOryctolagus9984Greylag gooseType 1specificAnser anser8843Guinea henType 1specificNumida meleagris8996HorseType 1specificEquus caballus9796Mallard duckType 1specificAnas platyrhynchos8839Mountain hareType 1specificLepus timidus62621Mule deerType 1specificOdocoileus9871OstrichType 1specificStruthio camelus8801PheasantType 1specificPhasianus colchicus9054QuailType 1specificPhasianidae9005RabbitType 1specificLeporidae9979Rock ptarmiganType 1specificLagopus muta64668Sheep (Mutton, Lamb)Type 1specificOvis aries9940SquabType 1specificColumba8931TurkeyType 1specificMeleagris gallopavo9103Velvet duckType 1specificMelanitta fusca371864Wild boarType 1specificSus scrofa9823