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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
Structure of 5-Methoxytryptamine

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

HIDE SMILES / InChI

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

Curator's Comment: referenced study was conducted in rat

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P08908
Gene ID: 3350.0
Gene Symbol: HTR1A
Target Organism: Homo sapiens (Human)
Target ID: P28223
Gene ID: 3356.0
Gene Symbol: HTR2A
Target Organism: Homo sapiens (Human)
Target ID: Q13639|||Q9NY73
Gene ID: 3360.0
Gene Symbol: HTR4
Target Organism: Homo sapiens (Human)
Target ID: P50406
Gene ID: 3362.0
Gene Symbol: HTR6
Target Organism: Homo sapiens (Human)
7.9 null [pKi]
Target ID: P34969
Gene ID: 3363.0
Gene Symbol: HTR7
Target Organism: Homo sapiens (Human)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Metabolism of the psychotomimetic tryptamine derivative 5-methoxy-N,N-diisopropyltryptamine in humans: identification and quantification of its urinary metabolites.
2006-02
Determination of melatonin and its precursors and metabolites using capillary electrophoresis with UV and fluorometric detection.
2005-11
[Melatoninergic receptor agonists and antagonists: pharmacological aspects and therapeutic perspective].
2005-11
Indoleamines and 5-methoxyindoles in trout pineal organ in vivo: daily changes and influence of photoperiod.
2005-10
Melatonin, a potent agent in antioxidative defense: actions as a natural food constituent, gastrointestinal factor, drug and prodrug.
2005-09-10
5-HT1A receptor agonists modify epileptic seizures in three experimental models in rats.
2005-09
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
Impact of the CYP2D6 ultra-rapid metabolizer genotype on doxepin pharmacokinetics and serotonin in platelets.
2005-08
Statistical distribution of blood serotonin as a predictor of early autistic brain abnormalities.
2005-07-19
Serotonin 5-HT7 receptors coupled to induction of interleukin-6 in human microglial MC-3 cells.
2005-07
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
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
Evidence for 5-HT2B and 5-HT7 receptor-mediated relaxation in pulmonary arteries of weaned pigs.
2005-01
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
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
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
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
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
Patents

Sample Use Guides

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
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
by admin
on Mon Mar 31 18:53:22 GMT 2025
Edited
by admin
on Mon Mar 31 18:53:22 GMT 2025
Record UNII
3VMW6141KC
Record Status Validated (UNII)
Record Version
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Name Type Language
5-Methoxytryptamine
MI  
Systematic Name English
MELATONIN RELATED COMPOUND A
DSC   USP-RS  
Preferred Name English
1H-INDOLE-3-ETHANAMINE, 5-METHOXY-
Systematic Name English
METHOXYTRYPTAMINE
Systematic Name English
MELATONIN RELATED COMPOUND A [USP-RS]
Common Name English
5-METHOXY-1H-INDOLE-3-ETHANAMINE
Systematic Name English
NSC-56422
Code English
3-(2-AMINOETHYL)-5-METHOXYINDOLE
Systematic Name English
METHOXYTRYPTAMINE, 5-
Systematic Name English
MEKSAMIN
Common Name English
MEXAMINE
Common Name English
5-METHOXYTRYPTAMINE [MI]
Common Name English
O-METHYL SEROTONIN
Common Name English
DEACETYLMELATONIN
Common Name English
MELATONIN RELATED COMPOUND A [DSC]
Common Name English
Classification Tree Code System Code
DSLD 3236 (Number of products:11)
Created by admin on Mon Mar 31 18:53:22 GMT 2025 , Edited by admin on Mon Mar 31 18:53:22 GMT 2025
Code System Code Type Description
ECHA (EC/EINECS)
210-153-7
Created by admin on Mon Mar 31 18:53:22 GMT 2025 , Edited by admin on Mon Mar 31 18:53:22 GMT 2025
PRIMARY
EPA CompTox
DTXSID60209638
Created by admin on Mon Mar 31 18:53:22 GMT 2025 , Edited by admin on Mon Mar 31 18:53:22 GMT 2025
PRIMARY
MESH
D008735
Created by admin on Mon Mar 31 18:53:22 GMT 2025 , Edited by admin on Mon Mar 31 18:53:22 GMT 2025
PRIMARY
RS_ITEM_NUM
1380116
Created by admin on Mon Mar 31 18:53:22 GMT 2025 , Edited by admin on Mon Mar 31 18:53:22 GMT 2025
PRIMARY
DAILYMED
3VMW6141KC
Created by admin on Mon Mar 31 18:53:22 GMT 2025 , Edited by admin on Mon Mar 31 18:53:22 GMT 2025
PRIMARY
SMS_ID
100000126316
Created by admin on Mon Mar 31 18:53:22 GMT 2025 , Edited by admin on Mon Mar 31 18:53:22 GMT 2025
PRIMARY
PUBCHEM
1833
Created by admin on Mon Mar 31 18:53:22 GMT 2025 , Edited by admin on Mon Mar 31 18:53:22 GMT 2025
PRIMARY
NSC
56422
Created by admin on Mon Mar 31 18:53:22 GMT 2025 , Edited by admin on Mon Mar 31 18:53:22 GMT 2025
PRIMARY
CHEBI
2089
Created by admin on Mon Mar 31 18:53:22 GMT 2025 , Edited by admin on Mon Mar 31 18:53:22 GMT 2025
PRIMARY
WIKIPEDIA
5-Methoxytryptamine
Created by admin on Mon Mar 31 18:53:22 GMT 2025 , Edited by admin on Mon Mar 31 18:53:22 GMT 2025
PRIMARY
CAS
608-07-1
Created by admin on Mon Mar 31 18:53:22 GMT 2025 , Edited by admin on Mon Mar 31 18:53:22 GMT 2025
PRIMARY
EVMPD
SUB32810
Created by admin on Mon Mar 31 18:53:22 GMT 2025 , Edited by admin on Mon Mar 31 18:53:22 GMT 2025
PRIMARY
MERCK INDEX
m7346
Created by admin on Mon Mar 31 18:53:22 GMT 2025 , Edited by admin on Mon Mar 31 18:53:22 GMT 2025
PRIMARY Merck Index
RXCUI
1426888
Created by admin on Mon Mar 31 18:53:22 GMT 2025 , Edited by admin on Mon Mar 31 18:53:22 GMT 2025
PRIMARY RxNorm
CHEBI
166874
Created by admin on Mon Mar 31 18:53:22 GMT 2025 , Edited by admin on Mon Mar 31 18:53:22 GMT 2025
PRIMARY
FDA UNII
3VMW6141KC
Created by admin on Mon Mar 31 18:53:22 GMT 2025 , Edited by admin on Mon Mar 31 18:53:22 GMT 2025
PRIMARY
Related Record Type Details
TARGET -> AGONIST
BINDING
IC50
Related Record Type Details
PARENT -> METABOLITE
Related Record Type Details
ACTIVE MOIETY