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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
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
Pineal indoles stimulate the gene expression of immunomodulating cytokines.
2001
Putative regulatory molecules in plants: evaluating melatonin.
2001 Aug
5HT4(a) and 5-HT4(b) receptors have nearly identical pharmacology and are both expressed in human atrium and ventricle.
2001 Feb
Endogenous indoles as novel polyamine site ligands at the N-methyl-D-aspartate receptor complex.
2001 Feb 2
High-performance liquid chromatography assay for indorenate in pharmaceutical powders.
2001 Jan
Unravelling the pharmacological profile of the canine external carotid vasodilator '5-HT1-like' receptors: coexistence of sympatho-inhibitory 5-HT1B and postjunctional 5-HT7 receptors.
2001 Jan
Effect of carrier excipient and processing on stability of indorenate hydrochloride/excipient mixtures.
2001 Nov
Examination of pineal indoles and 6-methoxy-2-benzoxazolinone for antioxidant and antimicrobial effects.
2001 Nov
[Presynaptic 5-hydroxytryptamine receptors enhance cholinergic neurosecretion in the human iris-ciliary body].
2001 Sep
Clinical safety and effectiveness of indorenate in essential hypertension.
2002
Modulation by serotonin 5-HT(4) receptors of long-term potentiation and depotentiation in the dentate gyrus of freely moving rats.
2002 Feb
Fourier transform infrared spectra and molecular structure of 5-methoxytryptamine, N-acetyl-5-methoxytryptamine and N-phenylsulfonamide-5-methoxytryptamine.
2003 Apr
Relative reactivities of histamine and indoleamines with acetaldehyde.
2003 Aug
Photoperiod affects amplitude but not duration of in vitro melatonin production in the ruin lizard (Podarcis sicula).
2003 Feb
Reduction of cisplatin-induced anemia by the pineal indole 5-methoxytryptamine in metastatic lung cancer patients.
2003 Feb-Apr
Circadian rhythms, oxidative stress, and antioxidative defense mechanisms.
2003 Nov
Early serotonergic projections to Cajal-Retzius cells: relevance for cortical development.
2004 Feb 18
Endogenous and dietary indoles: a class of antioxidants and radical scavengers in the ABTS assay.
2004 Mar
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 Nov
Rapid, accurate and precise quantitative drug analysis: comparing liquid chromatography tandem mass spectrometry and chip-based nanoelectrospray ionisation mass spectrometry.
2005
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 Jan
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 May 28
5-HT1A receptor agonists modify epileptic seizures in three experimental models in rats.
2005 Sep
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.
Name Type Language
5-METHOXYTRYPTAMINE
MI  
Systematic 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
MELATONIN RELATED COMPOUND A
DSC   USP-RS  
Common 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 Fri Dec 15 17:48:37 GMT 2023 , Edited by admin on Fri Dec 15 17:48:37 GMT 2023
Code System Code Type Description
ECHA (EC/EINECS)
210-153-7
Created by admin on Fri Dec 15 17:48:37 GMT 2023 , Edited by admin on Fri Dec 15 17:48:37 GMT 2023
PRIMARY
EPA CompTox
DTXSID60209638
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PRIMARY
MESH
D008735
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PRIMARY
RS_ITEM_NUM
1380116
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DAILYMED
3VMW6141KC
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SMS_ID
100000126316
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PRIMARY
PUBCHEM
1833
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NSC
56422
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PRIMARY
CHEBI
2089
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PRIMARY
WIKIPEDIA
5-Methoxytryptamine
Created by admin on Fri Dec 15 17:48:37 GMT 2023 , Edited by admin on Fri Dec 15 17:48:37 GMT 2023
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CAS
608-07-1
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PRIMARY
EVMPD
SUB32810
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PRIMARY
MERCK INDEX
m7346
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PRIMARY Merck Index
RXCUI
1426888
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PRIMARY RxNorm
CHEBI
166874
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PRIMARY
FDA UNII
3VMW6141KC
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PRIMARY