Hydroxytryptophol (5-hydroxytryptophol) is a naturally occurring indole derivative that is found in mammals, insects, and plants. It is a metabolite of serotonin, and is produced by the enzyme monoamine oxidase A (MAO-A). Hydroxytryptophol is thought to play a role in the regulation of sleep, appetite, and mood. It has also been shown to have antioxidant and anti-inflammatory properties. Research on hydroxytryptophol is ongoing, with the aim of understanding its role in human health and potential therapeutic applications.'
Hydroxytryptophol: 5-Hydroxy-indole-3-ethanol.
ID Source | ID |
---|---|
PubMed CID | 9061 |
CHEBI ID | 89825 |
SCHEMBL ID | 233744 |
MeSH ID | M0010789 |
Synonym |
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3-(2-hydroxyethyl)-1h-indol-5-ol |
5-hydroxyindole-3-ethanol |
brn 0143517 |
einecs 205-820-4 |
nsc 84416 |
hydroxytryptophol |
5-hydroxy-1h-indole-3-ethanol |
nsc-84416 |
154-02-9 |
5-hydroxytryptophol |
1h-indole-3-ethanol, 5-hydroxy- |
nsc84416 |
indole-3-ethanol, 5-hydroxy- |
H-8500 |
kqrohcsyogbqgj-uhfffaoysa- |
inchi=1/c10h11no2/c12-4-3-7-6-11-10-2-1-8(13)5-9(7)10/h1-2,5-6,11-13h,3-4h2 |
AKOS004911590 |
52mne52qa1 , |
4-21-00-02181 (beilstein handbook reference) |
unii-52mne52qa1 |
5-hydroxyindol |
FT-0670204 |
5-hydroxy tryptophol |
FT-0620499 |
SCHEMBL233744 |
3-(2-hydroxy-ethyl)-1h-indol-5-ol |
3-(2-hydroxyethyl)-1h-indol-5-ol # |
DTXSID80165505 |
mfcd00047197 |
CHEBI:89825 |
5-hydroxy-indole-acetic acid |
5-hydroxyindole-acetic acid |
5-hydroxyindoacetic acid |
5-htol |
5-hydroxy-1h-indole-3-ethanol(9ci) |
5-hydroxyindolacetate |
5-hydroxy-3-(2-hydroxyethyl)-indole |
HY-W041019 |
CS-W021759 |
Q27162013 |
AS-37867 |
tryptophol, 5-hydroxy- |
5-hydroxyindole-3-(2-hydroxy)ethyl |
5-hydroxy-3-(2-hydroxyethyl)indole |
AMY32000 |
bdbm428840 |
us10544152, cpd # 27 |
phosphatestandard |
PD018434 |
Excerpt | Relevance | Reference |
---|---|---|
" Treatment with 5-HTOL shifted the dose-response curve for 5-HT to the right and downward in a dose-dependent manner, but did not attenuate the contractile response to prostaglandin F2a." | ( Effects of 5-hydroxytryptophol, a 5-hydroxytryptamine metabolite, on isolated cerebral arteries of the dog. Hayashi, S; Toda, N; Wang Fu, LH, 1980) | 0.63 |
Class | Description |
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indoles | Any compound containing an indole skeleton. |
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res] |
Pathway | Proteins | Compounds |
---|---|---|
superpathway of tryptophan utilization | 42 | 92 |
serotonin degradation | 7 | 21 |
Timeframe | Studies, This Drug (%) | All Drugs % |
---|---|---|
pre-1990 | 56 (47.46) | 18.7374 |
1990's | 30 (25.42) | 18.2507 |
2000's | 29 (24.58) | 29.6817 |
2010's | 2 (1.69) | 24.3611 |
2020's | 1 (0.85) | 2.80 |
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] |
According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.
| This Compound (24.21) All Compounds (24.57) |
Publication Type | This drug (%) | All Drugs (%) |
---|---|---|
Trials | 4 (3.20%) | 5.53% |
Reviews | 7 (5.60%) | 6.00% |
Case Studies | 3 (2.40%) | 4.05% |
Observational | 0 (0.00%) | 0.25% |
Other | 111 (88.80%) | 84.16% |
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] |
Substance | Relationship Strength | Studies | Trials | Classes | Roles |
---|---|---|---|---|---|
gamma-aminobutyric acid gamma-Aminobutyric Acid: The most common inhibitory neurotransmitter in the central nervous system.. gamma-aminobutyric acid : A gamma-amino acid that is butanoic acid with the amino substituent located at C-4. | 2.66 | 3 | 0 | amino acid zwitterion; gamma-amino acid; monocarboxylic acid | human metabolite; neurotransmitter; Saccharomyces cerevisiae metabolite; signalling molecule |
5-hydroxytryptophan 5-Hydroxytryptophan: The immediate precursor in the biosynthesis of SEROTONIN from tryptophan. It is used as an antiepileptic and antidepressant.. 5-hydroxytryptophan : A tryptophan derivative that is tryptophan substituted by a hydroxy group at position 5. | 3.92 | 13 | 0 | hydroxytryptophan | human metabolite; neurotransmitter |
acetaldehyde Acetaldehyde: A colorless, flammable liquid used in the manufacture of acetic acid, perfumes, and flavors. It is also an intermediate in the metabolism of alcohol. It has a general narcotic action and also causes irritation of mucous membranes. Large doses may cause death from respiratory paralysis.. acetaldehyde : The aldehyde formed from acetic acid by reduction of the carboxy group. It is the most abundant carcinogen in tobacco smoke.. aldehyde : A compound RC(=O)H, in which a carbonyl group is bonded to one hydrogen atom and to one R group.. acetyl group : A group, formally derived from acetic acid by dehydroxylation, which is fundamental to the biochemistry of all forms of life. When bound to coenzyme A, it is central to the metabolism of carbohydrates and fats. | 5.02 | 5 | 0 | aldehyde | carcinogenic agent; EC 3.5.1.4 (amidase) inhibitor; electron acceptor; Escherichia coli metabolite; human metabolite; mouse metabolite; mutagen; oxidising agent; Saccharomyces cerevisiae metabolite; teratogenic agent |
3,4-dihydroxyphenylacetic acid 3,4-Dihydroxyphenylacetic Acid: A deaminated metabolite of LEVODOPA.. (3,4-dihydroxyphenyl)acetic acid : A dihydroxyphenylacetic acid having the two hydroxy substituents located at the 3- and 4-positions. It is a metabolite of dopamine.. dihydroxyphenylacetic acid : A dihydroxy monocarboxylic acid consisting of phenylacetic acid having two phenolic hydroxy substituents. | 2.9 | 4 | 0 | catechols; dihydroxyphenylacetic acid | human metabolite |
formaldehyde paraform: polymerized formaldehyde; RN given refers to parent cpd; used in root canal therapy | 1.96 | 1 | 0 | aldehyde; one-carbon compound | allergen; carcinogenic agent; disinfectant; EC 3.5.1.4 (amidase) inhibitor; environmental contaminant; Escherichia coli metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite |
hydrogen Hydrogen: The first chemical element in the periodic table with atomic symbol H, and atomic number 1. Protium (atomic weight 1) is by far the most common hydrogen isotope. Hydrogen also exists as the stable isotope DEUTERIUM (atomic weight 2) and the radioactive isotope TRITIUM (atomic weight 3). Hydrogen forms into a diatomic molecule at room temperature and appears as a highly flammable colorless and odorless gas.. dihydrogen : An elemental molecule consisting of two hydrogens joined by a single bond. | 2 | 1 | 0 | elemental hydrogen; elemental molecule; gas molecular entity | antioxidant; electron donor; food packaging gas; fuel; human metabolite |
indoleacetic acid indoleacetic acid: RN given refers to unlabeled parent cpd; structure in Merck Index, 9th ed, #4841. auxin : Any of a group of compounds, both naturally occurring and synthetic, that induce cell elongation in plant stems (from Greek alphaupsilonxialphanuomega, "to grow").. indole-3-acetic acid : A monocarboxylic acid that is acetic acid in which one of the methyl hydrogens has been replaced by a 1H-indol-3-yl group. | 2.21 | 1 | 0 | indole-3-acetic acids; monocarboxylic acid | auxin; human metabolite; mouse metabolite; plant hormone; plant metabolite |
methanol Methanol: A colorless, flammable liquid used in the manufacture of FORMALDEHYDE and ACETIC ACID, in chemical synthesis, antifreeze, and as a solvent. Ingestion of methanol is toxic and may cause blindness.. primary alcohol : A primary alcohol is a compound in which a hydroxy group, -OH, is attached to a saturated carbon atom which has either three hydrogen atoms attached to it or only one other carbon atom and two hydrogen atoms attached to it.. methanol : The primary alcohol that is the simplest aliphatic alcohol, comprising a methyl and an alcohol group. | 7.93 | 4 | 0 | alkyl alcohol; one-carbon compound; primary alcohol; volatile organic compound | amphiprotic solvent; Escherichia coli metabolite; fuel; human metabolite; mouse metabolite; Mycoplasma genitalium metabolite |
melatonin [no description available] | 5.37 | 19 | 0 | acetamides; tryptamines | anticonvulsant; central nervous system depressant; geroprotector; hormone; human metabolite; immunological adjuvant; mouse metabolite; radical scavenger |
n-acetylserotonin N-acetylserotonin : An N-acylserotonin resulting from the formal condensation of the primary amino group of serotonin with the carboxy group of acetic acid. | 3.85 | 12 | 0 | acetamides; N-acylserotonin; phenols | antioxidant; human metabolite; mouse metabolite; tropomyosin-related kinase B receptor agonist |
niacinamide nicotinamide : A pyridinecarboxamide that is pyridine in which the hydrogen at position 3 is replaced by a carboxamide group. | 1.94 | 1 | 0 | pyridine alkaloid; pyridinecarboxamide; vitamin B3 | anti-inflammatory agent; antioxidant; cofactor; EC 2.4.2.30 (NAD(+) ADP-ribosyltransferase) inhibitor; EC 3.5.1.98 (histone deacetylase) inhibitor; Escherichia coli metabolite; geroprotector; human urinary metabolite; metabolite; mouse metabolite; neuroprotective agent; Saccharomyces cerevisiae metabolite; Sir2 inhibitor |
pteridines [no description available] | 1.95 | 1 | 0 | azaarene; mancude organic heterobicyclic parent; ortho-fused heteroarene; pteridines | |
pyrazole 1H-pyrazole : The 1H-tautomer of pyrazole. | 6.96 | 1 | 0 | pyrazole | |
tryptamine [no description available] | 1.96 | 1 | 0 | aminoalkylindole; aralkylamino compound; indole alkaloid; tryptamines | human metabolite; mouse metabolite; plant metabolite |
1,10-phenanthroline 1,10-phenanthroline: RN given refers to parent cpd; inhibits Zn-dependent metalloproteinases | 1.96 | 1 | 0 | phenanthroline | EC 2.7.1.1 (hexokinase) inhibitor; EC 3.4.19.3 (pyroglutamyl-peptidase I) inhibitor |
3-methoxytyramine 3-methoxytyramine: RN given refers to parent cpd. 3-methoxytyramine : A monomethoxybenzene that is dopamine in which the hydroxy group at position 3 is replaced by a methoxy group. It is a metabolite of the neurotransmitter dopamine and considered a potential biomarker of pheochromocytomas and paragangliomas. | 2.39 | 2 | 0 | monomethoxybenzene; phenols; phenylethylamine; primary amino compound | biomarker; human blood serum metabolite; human urinary metabolite |
homovanillic acid Homovanillic Acid: A 3-O-methyl ETHER of (3,4-dihydroxyphenyl)acetic acid.. homovanillate : A hydroxy monocarboxylic acid anion which is obtained by deprotonation of the carboxy group of homovanillic acid.. homovanillic acid : A monocarboxylic acid that is the 3-O-methyl ether of (3,4-dihydroxyphenyl)acetic acid. It is a catecholamine metabolite. | 2.39 | 2 | 0 | guaiacols; monocarboxylic acid | human metabolite; mouse metabolite |
phenytoin [no description available] | 1.95 | 1 | 0 | imidazolidine-2,4-dione | anticonvulsant; drug allergen; sodium channel blocker; teratogenic agent |
hydroxyindoleacetic acid (5-hydroxyindol-3-yl)acetic acid : A member of the class of indole-3-acetic acids that is indole-3-acetic acid substituted by a hydroxy group at C-5. | 9.46 | 71 | 2 | indole-3-acetic acids | drug metabolite; human metabolite; mouse metabolite |
5-methoxytryptamine 5-Methoxytryptamine: Serotonin derivative proposed as potentiator for hypnotics and sedatives.. 5-methoxytryptamine : A member of the class of tryptamines that is the methyl ether derivative of serotonin. | 2.37 | 2 | 0 | aromatic ether; primary amino compound; tryptamines | 5-hydroxytryptamine 2A receptor agonist; 5-hydroxytryptamine 2B receptor agonist; 5-hydroxytryptamine 2C receptor agonist; antioxidant; cardioprotective agent; human metabolite; mouse metabolite; neuroprotective agent; radiation protective agent; serotonergic agonist |
acetazolamide Acetazolamide: One of the CARBONIC ANHYDRASE INHIBITORS that is sometimes effective against absence seizures. It is sometimes useful also as an adjunct in the treatment of tonic-clonic, myoclonic, and atonic seizures, particularly in women whose seizures occur or are exacerbated at specific times in the menstrual cycle. However, its usefulness is transient often because of rapid development of tolerance. Its antiepileptic effect may be due to its inhibitory effect on brain carbonic anhydrase, which leads to an increased transneuronal chloride gradient, increased chloride current, and increased inhibition. (From Smith and Reynard, Textbook of Pharmacology, 1991, p337) | 1.95 | 1 | 0 | monocarboxylic acid amide; sulfonamide; thiadiazoles | anticonvulsant; diuretic; EC 4.2.1.1 (carbonic anhydrase) inhibitor |
citalopram Citalopram: A furancarbonitrile that is one of the serotonin uptake inhibitors used as an antidepressant. The drug is also effective in reducing ethanol uptake in alcoholics and is used in depressed patients who also suffer from TARDIVE DYSKINESIA in preference to tricyclic antidepressants, which aggravate dyskinesia.. citalopram : A racemate comprising equimolar amounts of (R)-citalopram and its enantiomer, escitalopram. It is used as an antidepressant, although only escitalopram is active.. 1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-5-carbonitrile : A nitrile that is 1,3-dihydro-2-benzofuran-5-carbonitrile in which one of the hydrogens at position 1 is replaced by a p-fluorophenyl group, while the other is replaced by a 3-(dimethylamino)propyl group. | 2.41 | 2 | 0 | 2-benzofurans; cyclic ether; nitrile; organofluorine compound; tertiary amino compound | |
diazepam Diazepam: A benzodiazepine with anticonvulsant, anxiolytic, sedative, muscle relaxant, and amnesic properties and a long duration of action. Its actions are mediated by enhancement of GAMMA-AMINOBUTYRIC ACID activity.. diazepam : A 1,4-benzodiazepinone that is 1,3-dihydro-2H-1,4-benzodiazepin-2-one substituted by a chloro group at position 7, a methyl group at position 1 and a phenyl group at position 5. | 2 | 1 | 0 | 1,4-benzodiazepinone; organochlorine compound | anticonvulsant; anxiolytic drug; environmental contaminant; sedative; xenobiotic |
disulfiram [no description available] | 4.46 | 5 | 1 | organic disulfide; organosulfur acaricide | angiogenesis inhibitor; antineoplastic agent; apoptosis inducer; EC 1.2.1.3 [aldehyde dehydrogenase (NAD(+))] inhibitor; EC 3.1.1.1 (carboxylesterase) inhibitor; EC 3.1.1.8 (cholinesterase) inhibitor; EC 5.99.1.2 (DNA topoisomerase) inhibitor; ferroptosis inducer; fungicide; NF-kappaB inhibitor |
fomepizole Fomepizole: A pyrazole and competitive inhibitor of ALCOHOL DEHYDROGENASE that is used for the treatment of poisoning by ETHYLENE GLYCOL or METHANOL.. fomepizole : A member of the class of pyrazoles that is 1H-pyrazole substituted by a methyl group at position 4. | 2.38 | 2 | 0 | pyrazoles | antidote; EC 1.1.1.1 (alcohol dehydrogenase) inhibitor; protective agent |
fusaric acid Fusaric Acid: A picolinic acid derivative isolated from various Fusarium species. It has been proposed for a variety of therapeutic applications but is primarily used as a research tool. Its mechanisms of action are poorly understood. It probably inhibits DOPAMINE BETA-HYDROXYLASE, the enzyme that converts dopamine to norepinephrine. It may also have other actions, including the inhibition of cell proliferation and DNA synthesis. | 1.98 | 1 | 0 | aromatic carboxylic acid; pyridines | |
ketanserin Ketanserin: A selective serotonin receptor antagonist with weak adrenergic receptor blocking properties. The drug is effective in lowering blood pressure in essential hypertension. It also inhibits platelet aggregation. It is well tolerated and is particularly effective in older patients.. ketanserin : A member of the class of quinazolines that is quinazoline-2,4(1H,3H)-dione which is substituted at position 3 by a 2-[4-(p-fluorobenzoyl)piperidin-1-yl]ethyl group. | 1.97 | 1 | 0 | aromatic ketone; organofluorine compound; piperidines; quinazolines | alpha-adrenergic antagonist; antihypertensive agent; cardiovascular drug; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; serotonergic antagonist |
ketoconazole 1-acetyl-4-(4-{[2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazine : A dioxolane that is 1,3-dioxolane which is substituted at positions 2, 2, and 4 by imidazol-1-ylmethyl, 2,4-dichlorophenyl, and [para-(4-acetylpiperazin-1-yl)phenoxy]methyl groups, respectively. | 2 | 1 | 0 | dichlorobenzene; dioxolane; ether; imidazoles; N-acylpiperazine; N-arylpiperazine | |
lorazepam Lorazepam: A benzodiazepine used as an anti-anxiety agent with few side effects. It also has hypnotic, anticonvulsant, and considerable sedative properties and has been proposed as a preanesthetic agent. | 1.96 | 1 | 0 | benzodiazepine | |
methadone Methadone: A synthetic opioid that is used as the hydrochloride. It is an opioid analgesic that is primarily a mu-opioid agonist. It has actions and uses similar to those of MORPHINE. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1082-3). methadone : A racemate comprising equimolar amounts of dextromethadone and levomethadone. It is a opioid analgesic which is used as a painkiller and as a substitute for heroin in the treatment of heroin addiction.. 6-(dimethylamino)-4,4-diphenylheptan-3-one : A ketone that is heptan-3-one substituted by a dimethylamino group at position 6 and two phenyl groups at position 4. | 7.42 | 2 | 0 | benzenes; diarylmethane; ketone; tertiary amino compound | |
methiothepin Methiothepin: A serotonin receptor antagonist in the CENTRAL NERVOUS SYSTEM used as an antipsychotic.. methiothepin : A dibenzothiepine that is 10,11-dihydrodibenzo[b,f]thiepine bearing additional methylthio and 4-methylpiperazin-1-yl substituents at positions 8 and 10 respectively. Potent 5-HT2 antagonist, also active as 5-HT1 antagonist. Differentiates 5-HT1D sub-types. Also displays affinity for rodent 5-HT5B, 5-HT5A, 5-HT7 and 5-HT6 receptors (pK1 values are 6.6, 7.0, 8.4 and 8.7 respectively). | 1.97 | 1 | 0 | aryl sulfide; dibenzothiepine; N-alkylpiperazine; tertiary amino compound | antipsychotic agent; dopaminergic antagonist; geroprotector; serotonergic antagonist |
methylphenidate Methylphenidate: A central nervous system stimulant used most commonly in the treatment of ATTENTION DEFICIT DISORDER in children and for NARCOLEPSY. Its mechanisms appear to be similar to those of DEXTROAMPHETAMINE. The d-isomer of this drug is referred to as DEXMETHYLPHENIDATE HYDROCHLORIDE.. methylphenidate : A racemate comprising equimolar amounts of the two threo isomers of methyl phenyl(piperidin-2-yl)acetate. A central stimulant and indirect-acting sympathomimetic, is used (generally as the hydrochloride salt) in the treatment of hyperactivity disorders in children and for the treatment of narcolepsy.. methyl phenyl(piperidin-2-yl)acetate : A amino acid ester that is methyl phenylacetate in which one of the hydrogens alpha to the carbonyl group is replaced by a piperidin-2-yl group. | 1.95 | 1 | 0 | beta-amino acid ester; methyl ester; piperidines | |
midazolam Midazolam: A short-acting hypnotic-sedative drug with anxiolytic and amnestic properties. It is used in dentistry, cardiac surgery, endoscopic procedures, as preanesthetic medication, and as an adjunct to local anesthesia. The short duration and cardiorespiratory stability makes it useful in poor-risk, elderly, and cardiac patients. It is water-soluble at pH less than 4 and lipid-soluble at physiological pH.. midazolam : An imidazobenzodiazepine that is 4H-imidazo[1,5-a][1,4]benzodiazepine which is substituted by a methyl, 2-fluorophenyl and chloro groups at positions 1, 6 and 8, respectively. | 2 | 1 | 0 | imidazobenzodiazepine; monofluorobenzenes; organochlorine compound | anticonvulsant; antineoplastic agent; anxiolytic drug; apoptosis inducer; central nervous system depressant; GABAA receptor agonist; general anaesthetic; muscle relaxant; sedative |
clorgyline Clorgyline: An antidepressive agent and monoamine oxidase inhibitor related to PARGYLINE.. clorgyline : An aromatic ether that is the 2,4-dichlorophenyl ether of 3-aminopropan-1-ol in which the nitrogen is substituted by a methyl group and a prop-1-yn-3-yl group. A monoamine oxidase inhibitor, it was formerly used as an antidepressant. | 1.97 | 1 | 0 | aromatic ether; dichlorobenzene; terminal acetylenic compound; tertiary amino compound | antidepressant; EC 1.4.3.4 (monoamine oxidase) inhibitor |
pargyline Pargyline: A monoamine oxidase inhibitor with antihypertensive properties. | 1.95 | 1 | 0 | aromatic amine | |
probenecid Probenecid: The prototypical uricosuric agent. It inhibits the renal excretion of organic anions and reduces tubular reabsorption of urate. Probenecid has also been used to treat patients with renal impairment, and, because it reduces the renal tubular excretion of other drugs, has been used as an adjunct to antibacterial therapy.. probenecid : A sulfonamide in which the nitrogen of 4-sulfamoylbenzoic acid is substituted with two propyl groups. | 1.97 | 1 | 0 | benzoic acids; sulfonamide | uricosuric drug |
propranolol Propranolol: A widely used non-cardioselective beta-adrenergic antagonist. Propranolol has been used for MYOCARDIAL INFARCTION; ARRHYTHMIA; ANGINA PECTORIS; HYPERTENSION; HYPERTHYROIDISM; MIGRAINE; PHEOCHROMOCYTOMA; and ANXIETY but adverse effects instigate replacement by newer drugs.. propranolol : A propanolamine that is propan-2-ol substituted by a propan-2-ylamino group at position 1 and a naphthalen-1-yloxy group at position 3. | 1.97 | 1 | 0 | naphthalenes; propanolamine; secondary amine | anti-arrhythmia drug; antihypertensive agent; anxiolytic drug; beta-adrenergic antagonist; environmental contaminant; human blood serum metabolite; vasodilator agent; xenobiotic |
sodium fluoride [no description available] | 2 | 1 | 0 | fluoride salt | mutagen |
lysergic acid diethylamide Lysergic Acid Diethylamide: Semisynthetic derivative of ergot (Claviceps purpurea). It has complex effects on serotonergic systems including antagonism at some peripheral serotonin receptors, both agonist and antagonist actions at central nervous system serotonin receptors, and possibly effects on serotonin turnover. It is a potent hallucinogen, but the mechanisms of that effect are not well understood.. lysergic acid diethylamide : An ergoline alkaloid arising from formal condensation of lysergic acid with diethylamine. | 1.97 | 1 | 0 | ergoline alkaloid; monocarboxylic acid amide; organic heterotetracyclic compound | dopamine agonist; hallucinogen; serotonergic agonist |
thyroxine Thyroxine: The major hormone derived from the thyroid gland. Thyroxine is synthesized via the iodination of tyrosines (MONOIODOTYROSINE) and the coupling of iodotyrosines (DIIODOTYROSINE) in the THYROGLOBULIN. Thyroxine is released from thyroglobulin by proteolysis and secreted into the blood. Thyroxine is peripherally deiodinated to form TRIIODOTHYRONINE which exerts a broad spectrum of stimulatory effects on cell metabolism.. thyroxine : An iodothyronine compound having iodo substituents at the 3-, 3'-, 5- and 5'-positions. | 1.95 | 1 | 0 | 2-halophenol; iodophenol; L-phenylalanine derivative; non-proteinogenic L-alpha-amino acid; thyroxine zwitterion; thyroxine | antithyroid drug; human metabolite; mouse metabolite; thyroid hormone |
triiodothyronine Triiodothyronine: A T3 thyroid hormone normally synthesized and secreted by the thyroid gland in much smaller quantities than thyroxine (T4). Most T3 is derived from peripheral monodeiodination of T4 at the 5' position of the outer ring of the iodothyronine nucleus. The hormone finally delivered and used by the tissues is mainly T3.. 3,3',5-triiodo-L-thyronine : An iodothyronine compound having iodo substituents at the 3-, 3'- and 5-positions. Although some is produced in the thyroid, most of the 3,3',5-triiodo-L-thyronine in the body is generated by mono-deiodination of L-thyroxine in the peripheral tissues. Its metabolic activity is about 3 to 5 times that of L-thyroxine. The sodium salt is used in the treatment of hypothyroidism. | 1.95 | 1 | 0 | 2-halophenol; amino acid zwitterion; iodophenol; iodothyronine | human metabolite; mouse metabolite; thyroid hormone |
cyanides Cyanides: Inorganic salts of HYDROGEN CYANIDE containing the -CN radical. The concept also includes isocyanides. It is distinguished from NITRILES, which denotes organic compounds containing the -CN radical.. cyanides : Salts and C-organyl derivatives of hydrogen cyanide, HC#N.. isocyanide : The isomer HN(+)#C(-) of hydrocyanic acid, HC#N, and its hydrocarbyl derivatives RNC (RN(+)#C(-)).. cyanide : A pseudohalide anion that is the conjugate base of hydrogen cyanide. | 2.36 | 2 | 0 | pseudohalide anion | EC 1.9.3.1 (cytochrome c oxidase) inhibitor |
phenylethyl alcohol Phenylethyl Alcohol: An antimicrobial, antiseptic, and disinfectant that is used also as an aromatic essence and preservative in pharmaceutics and perfumery.. 2-phenylethanol : A primary alcohol that is ethanol substituted by a phenyl group at position 2. | 2.21 | 1 | 0 | benzenes; primary alcohol | Aspergillus metabolite; fragrance; plant growth retardant; plant metabolite; Saccharomyces cerevisiae metabolite |
tyrosine Tyrosine: A non-essential amino acid. In animals it is synthesized from PHENYLALANINE. It is also the precursor of EPINEPHRINE; THYROID HORMONES; and melanin.. tyrosine : An alpha-amino acid that is phenylalanine bearing a hydroxy substituent at position 4 on the phenyl ring. | 1.98 | 1 | 0 | amino acid zwitterion; erythrose 4-phosphate/phosphoenolpyruvate family amino acid; L-alpha-amino acid; proteinogenic amino acid; tyrosine | EC 1.3.1.43 (arogenate dehydrogenase) inhibitor; fundamental metabolite; micronutrient; nutraceutical |
desoxycorticosterone Desoxycorticosterone: A steroid metabolite that is the 11-deoxy derivative of CORTICOSTERONE and the 21-hydroxy derivative of PROGESTERONE | 1.97 | 1 | 0 | 20-oxo steroid; 21-hydroxy steroid; 3-oxo-Delta(4) steroid; mineralocorticoid; primary alpha-hydroxy ketone | human metabolite; mouse metabolite |
tryptophan Tryptophan: An essential amino acid that is necessary for normal growth in infants and for NITROGEN balance in adults. It is a precursor of INDOLE ALKALOIDS in plants. It is a precursor of SEROTONIN (hence its use as an antidepressant and sleep aid). It can be a precursor to NIACIN, albeit inefficiently, in mammals.. tryptophan : An alpha-amino acid that is alanine bearing an indol-3-yl substituent at position 3. | 8.92 | 13 | 0 | erythrose 4-phosphate/phosphoenolpyruvate family amino acid; L-alpha-amino acid zwitterion; L-alpha-amino acid; proteinogenic amino acid; tryptophan zwitterion; tryptophan | antidepressant; Escherichia coli metabolite; human metabolite; micronutrient; mouse metabolite; nutraceutical; plant metabolite; Saccharomyces cerevisiae metabolite |
arginine Arginine: An essential amino acid that is physiologically active in the L-form.. arginine : An alpha-amino acid that is glycine in which the alpha-is substituted by a 3-guanidinopropyl group. | 1.95 | 1 | 0 | arginine; glutamine family amino acid; L-alpha-amino acid; proteinogenic amino acid | biomarker; Escherichia coli metabolite; micronutrient; mouse metabolite; nutraceutical |
acetonitrile acetonitrile: RN given refers to unlabeled cpd. acetonitrile : A nitrile that is hydrogen cyanide in which the hydrogen has been replaced by a methyl group. | 2.08 | 1 | 0 | aliphatic nitrile; volatile organic compound | EC 3.5.1.4 (amidase) inhibitor; NMR chemical shift reference compound; polar aprotic solvent |
1,2,3,4-tetrahydroisoquinoline 1,2,3,4-tetrahydroisoquinoline: RN given refers to cpd with locants as specified | 1.96 | 1 | 0 | isoquinolines | |
isatin tribulin: endogenous MONOAMINE OXIDASE inhibitory activity extractable into ethyl acetate found in brain and many mammalian tissues and fluids; ISATIN is a major component; produced in excess following alcohol withdrawal; | 1.96 | 1 | 0 | indoledione | EC 1.4.3.4 (monoamine oxidase) inhibitor; plant metabolite |
benzylamine aminotoluene : Any member of the class of toluenes carrying one or more amino groups. | 2.08 | 1 | 0 | aralkylamine; primary amine | allergen; EC 3.5.5.1 (nitrilase) inhibitor; plant metabolite |
methysergide Methysergide: An ergot derivative that is a congener of LYSERGIC ACID DIETHYLAMIDE. It antagonizes the effects of serotonin in blood vessels and gastrointestinal smooth muscle, but has few of the properties of other ergot alkaloids. Methysergide is used prophylactically in migraine and other vascular headaches and to antagonize serotonin in the carcinoid syndrome.. methysergide : A synthetic ergot alkaloid, structurally related to the oxytocic agent methylergonovine and to the potent hallucinogen LSD and used prophylactically to reduce the frequency and intensity of severe vascular headaches. | 1.95 | 1 | 0 | ergoline alkaloid | |
cyanamide Cyanamide: A cyanide compound which has been used as a fertilizer, defoliant and in many manufacturing processes. It often occurs as the calcium salt, sometimes also referred to as cyanamide. The citrated calcium salt is used in the treatment of alcoholism.. cyanamide : A nitrile that is hydrogen cyanide in which the hydrogen has been replaced by an amino group. | 9.07 | 3 | 1 | nitrile; one-carbon compound | EC 1.2.1.3 [aldehyde dehydrogenase (NAD(+))] inhibitor |
fusarium Fusarium: A mitosporic Hypocreales fungal genus, various species of which are important parasitic pathogens of plants and a variety of vertebrates. Teleomorphs include GIBBERELLA. | 1.98 | 1 | 0 | ||
methoxytryptophol [no description available] | 8.35 | 7 | 0 | indoles | |
5-hydroxyindole [no description available] | 1.97 | 1 | 0 | hydroxyindoles | human metabolite |
5-methoxyindoleacetic acid 5-methoxyindoleacetic acid: serotonin metabolite. 5-methoxyindole-3-acetic acid : A member of the class of indole-3-acetic acids in which the hydrogen at position 5 of indole-3-acetic acid has been replaced by a methoxy group. | 1.96 | 1 | 0 | aromatic ether; indole-3-acetic acids | antibacterial agent; Brassica napus metabolite; carcinogenic agent; human urinary metabolite; marine xenobiotic metabolite; rat metabolite |
5,6-dihydroxytryptamine 5,6-Dihydroxytryptamine: Tryptamine substituted with two hydroxyl groups in positions 5 and 6. It is a neurotoxic serotonin analog that destroys serotonergic neurons preferentially and is used in neuropharmacologic research. | 1.97 | 1 | 0 | ||
deuterium Deuterium: The stable isotope of hydrogen. It has one neutron and one proton in the nucleus. | 2.38 | 2 | 0 | dihydrogen | |
vasotocin Vasotocin: A nonapeptide that contains the ring of OXYTOCIN and the side chain of ARG-VASOPRESSIN with the latter determining the specific recognition of hormone receptors. Vasotocin is the non-mammalian vasopressin-like hormone or antidiuretic hormone regulating water and salt metabolism.. vasotocin : A heterodetic cyclic peptide that is homologous to oxytocin and vasopressin. It is a pituitary hormone that acts as an endocrine regulator for water balance, osmotic homoeostasis and is involved in social and sexual behavior in non-mammalian vertebrates. | 3.75 | 3 | 0 | ||
selegiline Selegiline: A selective, irreversible inhibitor of Type B monoamine oxidase that is used for the treatment of newly diagnosed patients with PARKINSON DISEASE, and for the treatment of depressive disorders. The compound without isomeric designation is Deprenyl. | 1.97 | 1 | 0 | selegiline; terminal acetylenic compound | geroprotector |
transferrin Transferrin: An iron-binding beta1-globulin that is synthesized in the LIVER and secreted into the blood. It plays a central role in the transport of IRON throughout the circulation. A variety of transferrin isoforms exist in humans, including some that are considered markers for specific disease states. | 10.33 | 7 | 0 | ||
5,7-dihydroxytryptamine 5,7-Dihydroxytryptamine: Tryptamine substituted with two hydroxyl groups in positions 5 and 7. It is a neurotoxic serotonin analog that destroys serotonergic neurons preferentially and is used in neuropharmacology as a tool. | 2.01 | 1 | 0 | ||
1,7-phenanthroline [no description available] | 1.96 | 1 | 0 | phenanthroline | |
hydroxyindoleacetaldehyde (5-hydroxyindol-3-yl)acetaldehyde : An aldehyde that is acetaldehyde substituted by a 5-hydroxyindol-3-yl group. | 2 | 1 | 0 | hydroxyindoles; indoleacetaldehyde | human metabolite; mouse metabolite |
3,4-dihydroxyphenylethanol 3,4-dihydroxyphenylethanol: serotonin metabolite; structure | 2.21 | 1 | 0 | catechols; primary alcohol | antineoplastic agent; antioxidant; metabolite |
tryptoline tryptoline: neurotoxic factor that may be involved in development of Parkinson's disease; enzymatic prep from human brain converts tryptamine to tryptoline; RN given refers to parent cpd; structure | 1.96 | 1 | 0 | beta-carbolines | |
n-methylserotonin N-methylserotonin: RN given refers to parent cpd. N-methylserotonin : A member of the class of tryptamines that is serotonin in which one of the hydrogens attached to the primary amino group is replaced by a methyl group. | 2.04 | 1 | 0 | phenols; tryptamines | human metabolite; plant metabolite |
5-methoxytryptophan 5-methoxytryptophan: RN given refers to cpd without isomeric designation. 5-methoxytryptophan : An L-tryptophan derivative that is L-tryptophan with a methoxy substituent at position 5. | 1.96 | 1 | 0 | L-alpha-amino acid zwitterion; L-tryptophan derivative | metabolite |
6-hydroxytryptamine 6-hydroxytryptamine: RN given refers to parent cpd | 1.97 | 1 | 0 | ||
o-acetyl-5-methoxytryptophenol O-acetyl-5-methoxytryptophenol: synthesized in the pineal gland; structure given in first source | 2.36 | 2 | 0 | ||
isomethyleugenol Methylation: Addition of methyl groups. In histo-chemistry methylation is used to esterify carboxyl groups and remove sulfate groups by treating tissue sections with hot methanol in the presence of hydrochloric acid. (From Stedman, 25th ed) | 2.87 | 4 | 0 | isomethyleugenol | |
nad NAD(1-) : An anionic form of nicotinamide adenine dinucleotide arising from deprotonation of the two OH groups of the diphosphate moiety. | 2.36 | 2 | 0 | organophosphate oxoanion | cofactor; human metabolite; hydrogen acceptor; Saccharomyces cerevisiae metabolite |
beta-endorphin beta-Endorphin: A 31-amino acid peptide that is the C-terminal fragment of BETA-LIPOTROPIN. It acts on OPIOID RECEPTORS and is an analgesic. Its first four amino acids at the N-terminal are identical to the tetrapeptide sequence of METHIONINE ENKEPHALIN and LEUCINE ENKEPHALIN.. beta-endorphin : A polypeptide consisting of 31 amino acid residues in the sequence Tyr-Gly-Gly-Phe-Met-Thr-Ser-Glu-Lys-Ser-Gln-Thr-Pro-Leu-Val-Thr-Leu-Phe-Lys-Asn-Ala-Ile-Ile-Lys-Asn-Ala-Tyr-Lys-Lys-Gly-Glu. It is an endogenous opioid peptide neurotransmitter found in the neurons of both the central and peripheral nervous system and results from processing of the precursor protein proopiomelanocortin (POMC). | 1.96 | 1 | 0 | ||
ethyl glucuronide ethyl glucuronide: structure given in first source; RN given refers to (BETA-D)-isomer. ethyl glucuronide : A beta-D-glucosiduronic acid that is the ethyl derivative of beta-D-glucuronic acid. | 10.2 | 3 | 1 | beta-D-glucosiduronic acid | human urinary metabolite |
5-hydroxytryptophol glucuronide 5-hydroxytryptophol glucuronide: is the major excretion form of 5-hydroxytryptophol (5-HTOL), a minor serotonin metabolite under normal conditions | 2.72 | 3 | 0 | glycoside | |
phosphatidylethanol phosphatidylethanol: formed in rat brain by phospholipase D. phosphatidylethanol : A glycerophospholipid that is the monoethyl ester of any phosphatidic acid. | 4.03 | 2 | 0 | ||
acyclovir Acyclovir: A GUANOSINE analog that acts as an antimetabolite. Viruses are especially susceptible. Used especially against herpes.. acyclovir : An oxopurine that is guanine substituted by a (2-hydroxyethoxy)methyl substituent at position 9. Used in the treatment of viral infections. | 2.04 | 1 | 0 | 2-aminopurines; oxopurine | antimetabolite; antiviral drug |
isoxanthopterin [no description available] | 1.95 | 1 | 0 | dihydroxypteridine | |
neopterin [no description available] | 1.95 | 1 | 0 | ||
xanthopterin [no description available] | 1.95 | 1 | 0 | ||
2-amino-4-hydroxy-6-formylpteridine 2-amino-4-hydroxy-6-formylpteridine: pteridine precursor in biosynthesis of dihydropteroate; structure. 6-formylpterin : Pterin carrying a formyl group at position 6. | 1.95 | 1 | 0 | aldehyde; pterins | EC 1.17.3.2 (xanthine oxidase) inhibitor; reactive oxygen species generator |
Condition | Indicated | Relationship Strength | Studies | Trials |
---|---|---|---|---|
Alcohol Abuse [description not available] | 0 | 7.95 | 22 | 1 |
Alcoholism A primary, chronic disease with genetic, psychosocial, and environmental factors influencing its development and manifestations. The disease is often progressive and fatal. It is characterized by impaired control over drinking, preoccupation with the drug alcohol, use of alcohol despite adverse consequences, and distortions in thinking, most notably denial. Each of these symptoms may be continuous or periodic. (Morse & Flavin for the Joint Commission of the National Council on Alcoholism and Drug Dependence and the American Society of Addiction Medicine to Study the Definition and Criteria for the Diagnosis of Alcoholism: in JAMA 1992;268:1012-4) | 0 | 7.95 | 22 | 1 |
Alcohol Drinking Behaviors associated with the ingesting of ALCOHOLIC BEVERAGES, including social drinking. | 0 | 7.34 | 18 | 1 |
Adipocere [description not available] | 0 | 3.25 | 6 | 0 |
Drowning Death that occurs as a result of anoxia or heart arrest, associated with immersion in liquid. | 0 | 2.42 | 2 | 0 |
Sensitivity and Specificity Binary classification measures to assess test results. Sensitivity or recall rate is the proportion of true positives. Specificity is the probability of correctly determining the absence of a condition. (From Last, Dictionary of Epidemiology, 2d ed) | 0 | 2.91 | 4 | 0 |
Chemical Dependence [description not available] | 0 | 2.02 | 1 | 0 |
Apnea, Obstructive Sleep [description not available] | 0 | 2.02 | 1 | 0 |
Substance-Related Disorders Disorders related to substance use or abuse. | 0 | 2.02 | 1 | 0 |
Sleep Apnea, Obstructive A disorder characterized by recurrent apneas during sleep despite persistent respiratory efforts. It is due to upper airway obstruction. The respiratory pauses may induce HYPERCAPNIA or HYPOXIA. Cardiac arrhythmias and elevation of systemic and pulmonary arterial pressures may occur. Frequent partial arousals occur throughout sleep, resulting in relative SLEEP DEPRIVATION and daytime tiredness. Associated conditions include OBESITY; ACROMEGALY; MYXEDEMA; micrognathia; MYOTONIC DYSTROPHY; adenotonsilar dystrophy; and NEUROMUSCULAR DISEASES. (From Adams et al., Principles of Neurology, 6th ed, p395) | 0 | 2.02 | 1 | 0 |
Alcoholic Intoxication An acute brain syndrome which results from the excessive ingestion of ETHANOL or ALCOHOLIC BEVERAGES. | 0 | 4.98 | 9 | 0 |
Drug Withdrawal Symptoms [description not available] | 0 | 2.03 | 1 | 0 |
Substance Withdrawal Syndrome Physiological and psychological symptoms associated with withdrawal from the use of a drug after prolonged administration or habituation. The concept includes withdrawal from smoking or drinking, as well as withdrawal from an administered drug. | 0 | 2.03 | 1 | 0 |
Recrudescence [description not available] | 0 | 2.91 | 4 | 0 |
Addiction, Opioid [description not available] | 0 | 2.03 | 1 | 0 |
Drug Abuse, Intravenous [description not available] | 0 | 2.03 | 1 | 0 |
Opioid-Related Disorders Disorders related to or resulting from abuse or misuse of OPIOIDS. | 0 | 2.03 | 1 | 0 |
Dementia Praecox [description not available] | 0 | 2.04 | 1 | 0 |
Schizophrenia A severe emotional disorder of psychotic depth characteristically marked by a retreat from reality with delusion formation, HALLUCINATIONS, emotional disharmony, and regressive behavior. | 0 | 2.04 | 1 | 0 |
Psychoses [description not available] | 0 | 1.96 | 1 | 0 |
Depression Depressive states usually of moderate intensity in contrast with MAJOR DEPRESSIVE DISORDER present in neurotic and psychotic disorders. | 0 | 2.38 | 2 | 0 |
Pregnancy The status during which female mammals carry their developing young (EMBRYOS or FETUSES) in utero before birth, beginning from FERTILIZATION to BIRTH. | 0 | 1.96 | 1 | 0 |
Psychotic Disorders Disorders in which there is a loss of ego boundaries or a gross impairment in reality testing with delusions or prominent hallucinations. (From DSM-IV, 1994) | 0 | 1.96 | 1 | 0 |
Body Weight The mass or quantity of heaviness of an individual. It is expressed by units of pounds or kilograms. | 0 | 1.99 | 1 | 0 |
Acute Disease Disease having a short and relatively severe course. | 0 | 1.99 | 1 | 0 |
Clerambault Syndrome [description not available] | 0 | 1.99 | 1 | 0 |
Cancer of Digestive System [description not available] | 0 | 2 | 1 | 0 |
Complication, Postoperative [description not available] | 0 | 2 | 1 | 0 |
Digestive System Neoplasms Tumors or cancer of the DIGESTIVE SYSTEM. | 0 | 2 | 1 | 0 |
Postoperative Complications Pathologic processes that affect patients after a surgical procedure. They may or may not be related to the disease for which the surgery was done, and they may or may not be direct results of the surgery. | 0 | 2 | 1 | 0 |
Adult-Onset Dystonias [description not available] | 0 | 2 | 1 | 0 |
Dystonic Disorders Acquired and inherited conditions that feature DYSTONIA as a primary manifestation of disease. These disorders are generally divided into generalized dystonias (e.g., dystonia musculorum deformans) and focal dystonias (e.g., writer's cramp). They are also classified by patterns of inheritance and by age of onset. | 0 | 2 | 1 | 0 |
Lassitude [description not available] | 0 | 2 | 1 | 0 |
Bilateral Headache [description not available] | 0 | 2 | 1 | 0 |
Diarrhea An increased liquidity or decreased consistency of FECES, such as running stool. Fecal consistency is related to the ratio of water-holding capacity of insoluble solids to total water, rather than the amount of water present. Diarrhea is not hyperdefecation or increased fecal weight. | 0 | 2 | 1 | 0 |
Fatigue The state of weariness following a period of exertion, mental or physical, characterized by a decreased capacity for work and reduced efficiency to respond to stimuli. | 0 | 2 | 1 | 0 |
Headache The symptom of PAIN in the cranial region. It may be an isolated benign occurrence or manifestation of a wide variety of HEADACHE DISORDERS. | 0 | 2 | 1 | 0 |
Disease Models, Animal Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases. | 0 | 2.65 | 3 | 0 |
Myoclonic Jerk [description not available] | 0 | 2.65 | 3 | 0 |
Anoxia, Brain [description not available] | 0 | 2.36 | 2 | 0 |
Aging The gradual irreversible changes in structure and function of an organism that occur as a result of the passage of time. | 0 | 2.37 | 2 | 0 |
Nervous System Disorders [description not available] | 0 | 2.35 | 2 | 0 |
Ache [description not available] | 0 | 1.95 | 1 | 0 |
Nervous System Diseases Diseases of the central and peripheral nervous system. This includes disorders of the brain, spinal cord, cranial nerves, peripheral nerves, nerve roots, autonomic nervous system, neuromuscular junction, and muscle. | 0 | 2.35 | 2 | 0 |
Pain An unpleasant sensation induced by noxious stimuli which are detected by NERVE ENDINGS of NOCICEPTIVE NEURONS. | 0 | 1.95 | 1 | 0 |
Abdominal Migraine [description not available] | 0 | 1.95 | 1 | 0 |
Migraine Disorders A class of disabling primary headache disorders, characterized by recurrent unilateral pulsatile headaches. The two major subtypes are common migraine (without aura) and classic migraine (with aura or neurological symptoms). (International Classification of Headache Disorders, 2nd ed. Cephalalgia 2004: suppl 1) | 0 | 1.95 | 1 | 0 |
Leucocythaemia [description not available] | 0 | 1.95 | 1 | 0 |
Leukemia A progressive, malignant disease of the blood-forming organs, characterized by distorted proliferation and development of leukocytes and their precursors in the blood and bone marrow. Leukemias were originally termed acute or chronic based on life expectancy but now are classified according to cellular maturity. Acute leukemias consist of predominately immature cells; chronic leukemias are composed of more mature cells. (From The Merck Manual, 2006) | 0 | 1.95 | 1 | 0 |
Blood Pressure, High [description not available] | 0 | 1.97 | 1 | 0 |
Hypertension Persistently high systemic arterial BLOOD PRESSURE. Based on multiple readings (BLOOD PRESSURE DETERMINATION), hypertension is currently defined as when SYSTOLIC PRESSURE is consistently greater than 140 mm Hg or when DIASTOLIC PRESSURE is consistently 90 mm Hg or more. | 0 | 1.97 | 1 | 0 |