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
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 |
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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 |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Pineal indoles stimulate the gene expression of immunomodulating cytokines. | 2001 |
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Putative regulatory molecules in plants: evaluating melatonin. | 2001 Aug |
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5HT4(a) and 5-HT4(b) receptors have nearly identical pharmacology and are both expressed in human atrium and ventricle. | 2001 Feb |
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Endogenous indoles as novel polyamine site ligands at the N-methyl-D-aspartate receptor complex. | 2001 Feb 2 |
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High-performance liquid chromatography assay for indorenate in pharmaceutical powders. | 2001 Jan |
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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 |
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Effect of carrier excipient and processing on stability of indorenate hydrochloride/excipient mixtures. | 2001 Nov |
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Examination of pineal indoles and 6-methoxy-2-benzoxazolinone for antioxidant and antimicrobial effects. | 2001 Nov |
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[Presynaptic 5-hydroxytryptamine receptors enhance cholinergic neurosecretion in the human iris-ciliary body]. | 2001 Sep |
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Clinical safety and effectiveness of indorenate in essential hypertension. | 2002 |
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Modulation by serotonin 5-HT(4) receptors of long-term potentiation and depotentiation in the dentate gyrus of freely moving rats. | 2002 Feb |
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Fourier transform infrared spectra and molecular structure of 5-methoxytryptamine, N-acetyl-5-methoxytryptamine and N-phenylsulfonamide-5-methoxytryptamine. | 2003 Apr |
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Relative reactivities of histamine and indoleamines with acetaldehyde. | 2003 Aug |
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Photoperiod affects amplitude but not duration of in vitro melatonin production in the ruin lizard (Podarcis sicula). | 2003 Feb |
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Reduction of cisplatin-induced anemia by the pineal indole 5-methoxytryptamine in metastatic lung cancer patients. | 2003 Feb-Apr |
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Circadian rhythms, oxidative stress, and antioxidative defense mechanisms. | 2003 Nov |
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Early serotonergic projections to Cajal-Retzius cells: relevance for cortical development. | 2004 Feb 18 |
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Endogenous and dietary indoles: a class of antioxidants and radical scavengers in the ABTS assay. | 2004 Mar |
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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 Nov |
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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 |
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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 Jan |
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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 May 28 |
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5-HT1A receptor agonists modify epileptic seizures in three experimental models in rats. | 2005 Sep |
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.
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3236 (Number of products:11)
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ACTIVE MOIETY
PARENT (METABOLITE)