Psychedelics are substances (natural or laboratory made) which cause profound changes in a one’s perceptions of reality. While under the influence of hallucinogens, users might hallcuniate visually and auditorily.

This is an Experimental Substance with little data. This is most likely because the substance is is not very old. Information is limite and incomplete.

Disclaimer: Psychedelic drugs offer some of the most powerful and intense psychological experiences. Additionally these substances are illegal in many places. We understand that even though these substances are illegal, their use occurs frequently. We do not condone breaking of the law. By providing accurate information about these substances, we encourage the user to make responsible decisions and practice harm reduction.

Read the full disclaimer here.

Description

Mexamine Also known as:

  • 1H-Indole-3-ethanamine, 5-methoxy-[ACD/Index Name]
  • 2-(5-Methoxy-1H-indol-3-yl)ethanamin[German][ACD/IUPAC Name]
  • 2-(5-Methoxy-1H-indol-3-yl)ethanamine[ACD/IUPAC Name]
  • 2-(5-Méthoxy-1H-indol-3-yl)éthanamine[French][ACD/IUPAC Name]
  • 2-(5-methoxyindol-3-yl)ethylamine
  • 3-(2-aminoethyl)-5-methoxyindole
  • 5-Methoxyindole-3-ethanamine
  • 5-Mot
  • 5-MT
  • Deacetylmelatonin
  • Indole, 3- (2-aminoethyl)-5-methoxy-
  • meksamin
  • mexamine
  • O-methylserotonin
  • Tryptamine, 5-methoxy-
  • [2-(5-methoxy-1H-indol-3-yl)ethyl]amine
  • 2-(5-methoxy-1H-indol-3-yl)ethan-1-amine
  • 2-(5-methoxy-1H-indol-3-yl)ethylamine
  • 2-(5-Methoxy-1H-indol-3-yl)-ethylamine
  • 2-(5-methoxy-1H-indol-3-yl)ethylammonium
  • 2-[5-(Methyloxy)-1H-indol-3-yl]ethanamine
  • 2-[5-Methoxyindol-3-yl]ethylamine
  • 3-(2-Aminoethyl)-5-methoxy-1H-indole
  • 5 Methoxytryptamine
  • 5-MeOT
  • 5-methoxy-1H-indole-3-ethanamine
  • 5-methoxy-3-(2-aminoethyl)indole
  • 5-Methoxytryptamine-α,α,β,β-d4
  • Ethanamine,2-(5-methoxy-3-indolyl)-
  • Indole, 3-(2-aminoethyl)-5-methoxy-
  • Mexamine base

5-Methoxytryptamine, a tryptamine derivative that naturally occurs in the body at low levels. No evidence of recreational use. Apparently enhances dreams.

Chemistry

Common Name5-Methoxytryptamine
Systematic name5-Methoxytryptamine
FormulaC_{11}H_{14}N_{2}O
SMILESCOc1ccc2c(c1)c(c[nH]2)CCN
Std. InChiInChI=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
Std. InChiKeyJTEJPPKMYBDEMY-UHFFFAOYSA-N
Avg. Mass190.2417 Da
Molecular Weight190.2417
Monoisotopic Mass190.110611 Da
Nominal Mass190
ChemSpider ID1767

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Dose Chart

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Sources

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  652. Springer Nature Effect of pinealectomy and a constant high level of circulating melatonin or of 5-methoxytryptamine on the vasopressinergic innervation in the brain of the European hamster (Cricetus cricetus, L)
  653. Springer Nature Effect of precursors and some analogs of serotonin on the cerebral circulation
  654. Springer Nature Effect of the monoamine oxidase inhibitor indopan on experimental pneumococcal infection in rats
  655. Springer Nature Empfindliche und spezifische Bestimmung von Serotonin neben Tryptamin und 5-Methoxytryptamin mit der Hochdruckfl??ssig-Chromatographie
  656. Springer Nature Evidence for 5-HT2B and 5-HT7 receptor-mediated relaxation in pulmonary arteries of weaned pigs
  657. Springer Nature Immunohistochemistry of brain 5-hydroxytryptamine
  658. Springer Nature In-vitro uptake and metabolism of [3H]-5-hydroxytryptamine in the pineal glands of the rabbit, rat and hamster
  659. Springer Nature Indole derivatives
  660. Springer Nature Induction of cyst formation by low temperature in the dinoflagellateGonyaulax polyedra Stein: Dependence on circadian phase and requirement of light
  661. Springer Nature Influence of some pteridines on pineal 5-methoxy-indole synthesis in male wistar rats periodically exposed to either white or red light
  662. Springer Nature MAO inhibition and the effects of centrally administered LSD, serotonin, and 5-methoxytryptamine on the conditioned avoidance response in rats
  663. Springer Nature Mass-spectrometric investigation of some indole derivatives
  664. Springer Nature Mechanism of depression of the spinal pain syndrome by serotonin derivatives
  665. Springer Nature Mechanism of species differences in sensitivity of monkeys and dogs to the emetic action of various drugs
  666. Springer Nature Melatonin, hormone of darkness and more ? occurrence, control mechanisms, actions and bioactive metabolites
  667. Springer Nature Methoxyindole synthesis in the retina of the frog (rana esculenta) during a diurnal period
  668. Springer Nature Morning injections of large doses of melatonin, but not of 5-methoxytryptamine, prevent in the hamster the antigonadotropic effect of 5-methoxytryptamine administered late in the afternoon
  669. Springer Nature Nervous component in the mechanism of action of radioprotective substances
  670. Springer Nature null
  671. Springer Nature Physiological disposition of 5-methoxytryptamine and the rope climbing performance of rats
  672. Springer Nature Pineal indoles stimulate the gene expression of immunomodulating cytokines
  673. Springer Nature Pineal-thyroid interaction: Distorting effect of experimental partial thyroidectomy of antihydroid effect of pineal methoxyindoles
  674. Springer Nature Plasma concentrations of 5-methoxytryptamine, 5-methoxytryptophol and melatonin after 5-methoxytryptamine administration of golden hamsters: physiological implications
  675. Springer Nature Potentiation by deprenyl of the autoreceptor-mediated inhibition of [3H]-5-hydroxytryptamine release by 5-methoxytryptamine
  676. Springer Nature Radioprotective effect of immobilized cystamine
  677. Springer Nature Radioprotective effectiveness of some serotonin-like compounds
  678. Springer Nature Radioprotective properties of indralin combined with cystamine and mexamine
  679. Springer Nature Receptor-mediated effects of serotonin and 5-methoxytryptamine on noradrenaline release in the rat vena cava and in the heart of the pithed rat
  680. Springer Nature Receptors for 5-hydroxytryptamine on the sympathetic nerves of the rabbit heart
  681. Springer Nature SDZ 205-557, a selective, surmountable antagonist for 5-HT4 receptors in the isolated guinea pig ileum
  682. Springer Nature Seasonal variations in HIOMT activity during the night in the pineal gland of 21 day old male wistar rats
  683. Springer Nature Serotonin preparations
  684. Springer Nature Serotonin, serotoninergic agents and their antagonists suppress humoral immune reaction in vitro
  685. Springer Nature Simple methods of in vivo testing for peripheral M- and D-antagonists of serotonin
  686. Springer Nature Simultaneous detection of indoleamines and dopamine in rat dorsal raphe nuclei using specific antibodies
  687. Springer Nature Synthesis and hypoglycemic activity of N-acyl-5-methoxytryptamines
  688. Springer Nature Synthesis and pharmacological activity of 5,6-and 4,5-ethylenedioxytryptamines
  689. Springer Nature Synthesis of melatonin analogs
  690. Springer Nature The distribution of strictosidine-synthase activity and alkaloids in Cinchona plants
  691. Springer Nature The effect of melatonin and other indole derivatives in maintaining ovulation in rats kept in continuous light and the influence of these indoles on HIOMT activity in the pineal gland
  692. Springer Nature The effect of reduced neopterin on the synthesis of several methylated indoles in the pineal gland of adult male golden hamsters, kept under standardized conditions
  693. Springer Nature The independency of an intact pineal gland of the inhibition by 5-methoxytryptamine of the reproductive organs in the male hamster
  694. Springer Nature The influence of different 5-methoxyindoles on the process of protein/peptide secretion characterized by the formation of granular vesicles in the mouse pineal gland
  695. Springer Nature The influence of light of different wavelengths on the methylating capacity of the pineal gland of male golden hamsters in relation to reproduction
  696. Springer Nature The influence of simultaneously administered mexamine on the distribution of cystamine-35S
  697. Springer Nature The influence of some pteridines on pineal 5-methoxyindole synthesis in male Wistar rats periodically exposed to either white or green light
  698. Springer Nature The pineal gland of the mole (Talpa europaea L.) VII. Activity of hydroxyindole-O-methyltransferase (HIOMT) in the formation of 5-methoxytryptophan, 5-methoxytryptamine, 5-methoxyindole-3-acetic acid, 5-methoxytryptophol and melatonin in the eyes and the pineal gland
  699. Springer Nature The presence and function of melatonin and structurally related indoleamines in a dinoflagellate, and a hypothesis on the evolutionary significance of these tryptophan metabolites in unicellulars
  700. Springer Nature The role of the serotonergic system in foot shock-induced behavior in mice
  701. Springer Nature Ultrastructural characterization of asexual cysts ofGonyaulax polyedra Stein (Dinoflagellata)
  702. Springer Nature 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
  703. SynQuest 4H30-1-3V
  704. TCI M0131
  705. The Merck Index Online cs000000012269
  706. Thieme Chemistry SD-215-00090
  707. Thomson Pharma 00056735
  708. Timtec SBB002534
  709. Tractus Company Limited TC-071750
  710. Tractus Company Limited TRA0073390
  711. Urine Metabolome Database HMDB0004095
  712. Vitas-M STK386888
  713. VulcanChem VC250141
  714. W&J PharmaChem, Inc. 50A161999
  715. W&J PharmaChem, Inc. 50A161999
  716. Wikidata Q4352011
  717. Wikipedia 5-Methoxytryptamine
  718. ZINC ZINC00057163
  719. zjartschem ZCF09289

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