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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
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

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

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
7.9 null [pKi]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

PubMed

Sample Use Guides

In Vivo Use Guide
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
Record UNII
3VMW6141KC
Record Status Validated (UNII)
Record Version