Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C11H14N2O |
| Molecular Weight | 190.2417 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
COC1=CC2=C(NC=C2CCN)C=C1
InChI
InChIKey=JTEJPPKMYBDEMY-UHFFFAOYSA-N
InChI=1S/C11H14N2O/c1-14-9-2-3-11-10(6-9)8(4-5-12)7-13-11/h2-3,6-7,13H,4-5,12H2,1H3
| Molecular Formula | C11H14N2O |
| Molecular Weight | 190.2417 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
5-Methoxytryptamine (aka 5-MT, mexamine) is a tryptamine derivative closely related to the neurotransmitters serotonin and melatonin. 5-MT is produced endogenously at low levels; it is biosynthesized by deacetylation of melatonin in the pineal gland. 5-MT acts as a full agonist at the 5-HT1, 5-HT2, 5-HT4, 5-HT6, and 5-HT7 receptors. It is often used as a chemical probe in the study of serotonin receptors, but it has also been used in a clinical trial to mitigate the anemic effects of cisplatin chemotherapy.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/17825441
Curator's Comment: referenced study was conducted in rat
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: P08908 Gene ID: 3350.0 Gene Symbol: HTR1A Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/2966313 |
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Target ID: P28223 Gene ID: 3356.0 Gene Symbol: HTR2A Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/9128844 |
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Target ID: Q13639|||Q9NY73 Gene ID: 3360.0 Gene Symbol: HTR4 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/9128844 |
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Target ID: P50406 Gene ID: 3362.0 Gene Symbol: HTR6 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/9225298 |
7.9 null [pKi] | ||
Target ID: P34969 Gene ID: 3363.0 Gene Symbol: HTR7 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/10051134 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Metabolism of the psychotomimetic tryptamine derivative 5-methoxy-N,N-diisopropyltryptamine in humans: identification and quantification of its urinary metabolites. | 2006-02 |
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| Determination of melatonin and its precursors and metabolites using capillary electrophoresis with UV and fluorometric detection. | 2005-11 |
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| [Melatoninergic receptor agonists and antagonists: pharmacological aspects and therapeutic perspective]. | 2005-11 |
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| Indoleamines and 5-methoxyindoles in trout pineal organ in vivo: daily changes and influence of photoperiod. | 2005-10 |
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| Melatonin, a potent agent in antioxidative defense: actions as a natural food constituent, gastrointestinal factor, drug and prodrug. | 2005-09-10 |
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| 5-HT1A receptor agonists modify epileptic seizures in three experimental models in rats. | 2005-09 |
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| Sensitive determination of alpha-methyltryptamine (AMT) and 5-methoxy-N,N-diisopropyltryptamine (5MeO-DIPT) in whole blood and urine using gas chromatography-mass spectrometry. | 2005-08-25 |
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| Impact of the CYP2D6 ultra-rapid metabolizer genotype on doxepin pharmacokinetics and serotonin in platelets. | 2005-08 |
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| Statistical distribution of blood serotonin as a predictor of early autistic brain abnormalities. | 2005-07-19 |
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| Serotonin 5-HT7 receptors coupled to induction of interleukin-6 in human microglial MC-3 cells. | 2005-07 |
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| Clozapine attenuates the locomotor sensitisation and the prepulse inhibition deficit induced by a repeated oral administration of Catha edulis extract and cathinone in rats. | 2005-05-28 |
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| A foxy intoxication. | 2005-02-10 |
|
| Behavioral and cellular consequences of increasing serotonergic activity during brain development: a role in autism? | 2005-02 |
|
| Voltage-dependent inhibition of recombinant NMDA receptor-mediated currents by 5-hydroxytryptamine. | 2005-02 |
|
| Effect of the postsynaptic 5-HT1A receptor antagonist MM-77 on stressed mice treated with 5-HT1A receptor agents. | 2005-01-31 |
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| Evidence for 5-HT2B and 5-HT7 receptor-mediated relaxation in pulmonary arteries of weaned pigs. | 2005-01 |
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| Recovery from experimental Parkinson's disease in the 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine hydrochloride treated marmoset with the melatonin analogue ML-23. | 2005-01 |
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| Rapid, accurate and precise quantitative drug analysis: comparing liquid chromatography tandem mass spectrometry and chip-based nanoelectrospray ionisation mass spectrometry. | 2005 |
|
| The actions of a charged melatonin receptor ligand, TMEPI, and an irreversible MT2 receptor agonist, BMNEP, on mouse hippocampal evoked potentials in vitro. | 2004-11-12 |
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| Recovery of experimental Parkinson's disease with the melatonin analogues ML-23 and S-20928 in a chronic, bilateral 6-OHDA model: a new mechanism involving antagonism of the melatonin receptor. | 2004-11 |
|
| Analytical chemistry of synthetic routes to psychoactive tryptamines. Part I. Characterisation of the Speeter and Anthony synthetic route to 5-methoxy-N,N-diisopropyltryptamine using ESI-MS-MS and ESI-TOF-MS. | 2004-11 |
|
| Functional expression of the serotonin 5-HT7 receptor in human glioblastoma cell lines. | 2004-10 |
|
| A general screening and confirmation approach to the analysis of designer tryptamines and phenethylamines in blood and urine using GC-EI-MS and HPLC-electrospray-MS. | 2004-09 |
|
| [Latest cases of acute poisoning in clinical practice--5MeO-DIPT and GHB precursor]. | 2004-07 |
|
| Opposing electrophysiological actions of 5-HT on noncholinergic and cholinergic neurons in the rat ventral pallidum in vitro. | 2004-07 |
|
| Binding of tryptamine analogs at h5-HT1E receptors: a structure-affinity investigation. | 2004-05-15 |
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| Endogenous and dietary indoles: a class of antioxidants and radical scavengers in the ABTS assay. | 2004-03 |
|
| Inhibition of p38 mitogen-activated protein kinase enhances adrenergic-stimulated arylalkylamine N-acetyltransferase activity in rat pinealocytes. | 2004-03 |
|
| Early serotonergic projections to Cajal-Retzius cells: relevance for cortical development. | 2004-02-18 |
|
| Involvement of melatonin metabolites in the long-term inhibitory effect of the hormone on rat spinal nociceptive transmission. | 2004-02 |
|
| Molecular cloning and pharmacological characterization of the guinea pig 5-HT1E receptor. | 2004-01-26 |
|
| Selective scavenging property of the indole moiety for the nitrating species of peroxynitrite. | 2004-01 |
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| Synthesis of internal labeled standards of melatonin and its metabolite N1-acetyl-N2-formyl-5-methoxykynuramine for their quantification using an on-line liquid chromatography-electrospray tandem mass spectrometry system. | 2004-01 |
|
| Autoradiographic distribution of 5-HT7 receptors in the human brain using [3H]mesulergine: comparison to other mammalian species. | 2004-01 |
|
| Peroxynitrite scavenging activity of indole derivatives: interaction of indoles with peroxynitrite. | 2004 |
|
| The implementation of acute versus chronic animal models for treatment discovery in Parkinson's disease. | 2004 |
|
| Expression of human organic anion transporters in the choroid plexus and their interactions with neurotransmitter metabolites. | 2003-12 |
|
| Circadian rhythms, oxidative stress, and antioxidative defense mechanisms. | 2003-11 |
|
| Depression of mGluR-mediated IPSCs by 5-HT in dopamine neurons of the rat substantia nigra pars compacta. | 2003-11 |
|
| Interaction of singlet molecular oxygen with melatonin and related indoles. | 2003-11 |
|
| Pharmacological characterization of a serotonin receptor (5-HT7) stimulating cAMP production in human corneal epithelial cells. | 2003-11 |
|
| Foxy, a designer tryptamine hallucinogen. | 2003-08-12 |
|
| Relative reactivities of histamine and indoleamines with acetaldehyde. | 2003-08 |
|
| Characterization of the 5-HT6 receptor coupled to Ca2+ signaling using an enabling chimeric G-protein. | 2003-07-04 |
|
| [Levels of psilocybin and psilocin in various types of mushrooms]. | 2003-07 |
|
| Screening for endogenous substrates reveals that CYP2D6 is a 5-methoxyindolethylamine O-demethylase. | 2003-06 |
|
| In search of endogenous CYP2D6 substrates. | 2003-06 |
|
| Photochemical properties of kynurenine pathway metabolites and indoleamines. | 2003 |
|
| Total pineal endocrine substitution therapy (TPEST) as a new neuroendocrine palliative treatment of untreatable metastatic solid tumor patients: a phase II study. | 2002-10-27 |
|
| Human serotonin 1D receptor is encoded by a subfamily of two distinct genes: 5-HT1D alpha and 5-HT1D beta. | 1992-04-15 |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/12743539
To potentially mitigate the anemia resulting from cisplatin therapy, twenty patients with metastatic lung cancer who underwent chemotherapeutic combinations containing cisplatin were randomized to receive chemotherapy alone or chemotherapy plus 5-MT (daily 1 mg/day; oral). Hemoglobin mean-blood concentrations significantly decreased in both groups of patients. However, the decrease in hemoglobin levels observed in patients treated with chemotherapy alone was significantly higher with respect to that observed in patients concomitantly treated with 5-MTT. Moreover, the percent of patients who had no progressive disease on treatment was significantly higher in the group treated with chemotherapy plus 5-MTT.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2966313
Brain slices (400 micro-m) from the mid-portion of the hippocampus of male Wistar rats were perfused with artificial cerebrospinal fluid (ACSF) containing Na+ 154 mM, K+ 4.25 mM, CI- 131.5 mM, HCO3- 26 mM, H2PO4- 1.25 mM, Ca 2+ 2.0 mM, Mg 2+ 2.0 mM, SO42- 2.0 mM, glucose 10 mM. ACSF was maintained at 35 deg-C in a 5% CO2 atmosphere at pH 7.4. 3 M KC1 glass microelectrodes (50-180 MY2) were used for intracellular recordings. 5-HT-HCl was dissolved in the ACSF for focal pressure ejection micropipette application. 5-HT was applied as a very small drop into stratum oriens near the soma of the recorded CA1 neurons. Post-spike train afterhyperpolarizations (AHPs) were elicited by 100 ms constant current depolarizing pulses which generated 3-7 spikes. Hippocampal CA1 neurons consistently responded to 5-HT (10 -6 to 10 -4 M) application by producing a rapid-onset hyperpolarization. There were two types of 5-HT evoked hyperpolarization; a long-lasting hyperpolarizing response which, occurred only upon the first application of 5-HT in 65% of cells, and a short-lasting hyperpolarization often with an ensuing depolarization.
| Substance Class |
Chemical
Created
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admin
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Mon Mar 31 18:53:22 GMT 2025
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Mon Mar 31 18:53:22 GMT 2025
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| Record UNII |
3VMW6141KC
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Validated (UNII)
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3236 (Number of products:11)
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210-153-7
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DTXSID60209638
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D008735
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1380116
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3VMW6141KC
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100000126316
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2089
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5-Methoxytryptamine
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608-07-1
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SUB32810
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m7346
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1426888
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166874
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3VMW6141KC
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BINDING
IC50
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ACTIVE MOIETY |
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