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| | 5-Methoxytryptamine Basic information |
| | 5-Methoxytryptamine Chemical Properties |
| Melting point | 121-123 °C (lit.) | | Boiling point | 325.75°C (rough estimate) | | density | 1.0815 (rough estimate) | | refractive index | 1.5700 (estimate) | | storage temp. | 2-8°C | | solubility | Chloroform (Slightly), Methanol (Slightly) | | pka | 16.91±0.30(Predicted) | | form | crystalline | | color | white | | Merck | 13,6032 | | BRN | 145587 | | InChI | 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 | | InChIKey | JTEJPPKMYBDEMY-UHFFFAOYSA-N | | SMILES | N1C2=C(C=C(OC)C=C2)C(CCN)=C1 | | CAS DataBase Reference | 608-07-1(CAS DataBase Reference) | | NIST Chemistry Reference | 5-Methoxytryptamine(608-07-1) |
| Hazard Codes | Xn | | Risk Statements | 22-36/37/38-20/21/22 | | Safety Statements | 36-26 | | WGK Germany | 3 | | RTECS | NL4110000 | | F | 8 | | HS Code | 29339900 | | Toxicity | LD50 intraperitoneal in mouse: 176mg/kg |
| | 5-Methoxytryptamine Usage And Synthesis |
| Description | 5-Methoxytryptamine (5-MT), also known as mexamine, is a tryptamine derivative closely related to the neurotransmitters serotonin and melatonin. 5-MT has been shown to occur naturally in the body in low levels.It is biosynthesized via the deacetylation of melatonin in the pineal gland.
The protective effect of 5-methoxytryptamine (a metabolite of melatonin) in human keratinocytes against ultraviolet B (UVB) radiation was studied.
Melatonin and its metabolites ameliorate ultraviolet B-induced damage in human epidermal keratinocytes. | | Chemical Properties | White to tan crystalline powder | | Uses | 5-Methoxytryptamine (Mexamine, Methoxytryptamine) is a tryptamine derivative that is closely related to the neurotransmitter Melatonin (M215000) and Serotonin (S274980). It acts as a full agonist at the 5-HT1, 5-HT2, 5-HT4, 5-HT6, and 5-HT7 receptors but has no affinity for the 5-HT3 receptor. | | Definition | ChEBI: 5-methoxytryptamine is a member of the class of tryptamines that is the methyl ether derivative of serotonin. It has a role as a serotonergic agonist, a human metabolite, a mouse metabolite, a 5-hydroxytryptamine 2A receptor agonist, a 5-hydroxytryptamine 2C receptor agonist, a 5-hydroxytryptamine 2B receptor agonist, an antioxidant, a radiation protective agent, a neuroprotective agent and a cardioprotective agent. It is a member of tryptamines, an aromatic ether and a primary amino compound. It derives from a serotonin. It is a conjugate base of a 5-methoxytryptamine(1+). | | Application | 5-Methoxytryptamine was used as an agonist in the study of pharmacological profile of the 5-hydroxytryptamine 1 receptor.
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Tacrine-melatonin hybrids as multifunctional agents for alzheimer′s disease | | General Description | The protective effect of 5-methoxytryptamine (a metabolite of melatonin) in human keratinocytes against ultraviolet B (UVB) radiation was studied. | | Biochem/physiol Actions | Nonselective serotonin receptor agonist that lacks affinity for the 5-HT3 receptor. | | Synthesis | 5-Methoxytryptamine (358) was synthesized from 3-(2-iodoethyl)-5-methoxyindole (176) by reaction with 1-methyl-benzylamine (MeCN, 24 h, RT) and subsequent catalytic debenzylation of 44 (H2, Pd/C, EtOH, 24 h, RT, 4 bar). The resulting 5-methoxytryptamine (358 was then reacted with 4-bromobenzoylchloride (THF, NEt3, RT, ON) and the resulting tryptamide 359 was reduced with aluminum hydride to N-(4-bromobenzyl)-5-methoxytryptamine (19) (LiAlH4, AlCl3, Et2O, 5 h, RT), which was isolated as its hydrogen oxalate salt.
 | | Clinical claims and research | The effects of the 5-HT receptor agonist, 5-methoxytryptamine, on plasma glucose levels were investigated in rats. 5-Methoxytryptamine induced a significant hyperglycemia above the dosage of 1 mg/kg. 5-Methoxytryptamine-induced hyperglycemia was antagonized by pretreatment with the 5-HT1 and 5-HT2 receptor antagonist, methysergide, or the 5-HT2A receptor antagonist, ketanserin, whereas the 5-HT3 and 5-HT4 receptor antagonist, tropisetron, and the 5-HT4 receptor antagonist, SDZ 205-557 (2-methoxy-4-amino-5-chloro-benzoic acid 2-(diethylamino) ethyl ester), showed no effect. In addition, the peripheral 5-HT2 receptor antagonist, xylamidine, reduced 5-methoxytryptamine-induced hyperglycemia.
Hyperglycemia induced by the 5-HT receptor agonist, 5-methoxytryptamine, in rats: involvement of the peripheral 5-HT2A receptor. |
| | 5-Methoxytryptamine Preparation Products And Raw materials |
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