2-(5-Methoxyindol-3-yl)ethylamin

Bezeichnung:2-(5-Methoxyindol-3-yl)ethylamin

CAS-Nr608-07-1

Englisch Name:5-Methoxytryptamine

CBNumberCB0676885

SummenformelC11H14N2O

Molgewicht190.24

MOL-Datei608-07-1.mol

Synonyma

2-(5-Methoxyindol-3-yl)ethylamin

2-(5-Methoxyindol-3-yl)ethylamin physikalisch-chemischer Eigenschaften

Schmelzpunkt	121-123 °C (lit.)
Siedepunkt	325.75°C (rough estimate)
Dichte	1.0815 (rough estimate)
Brechungsindex	1.5700 (estimate)
storage temp.	2-8°C
Löslichkeit	Chloroform (Slightly), Methanol (Slightly)
Aggregatzustand	crystalline
pka	16.91±0.30(Predicted)
Farbe	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 Datenbank	608-07-1(CAS DataBase Reference)
NIST chemische Informationen	5-Methoxytryptamine(608-07-1)

Sicherheit

Kennzeichnung gefährlicher	Xn
R-Sätze:	22-36/37/38-20/21/22
S-Sätze:	36-26
WGK Germany	3
RTECS-Nr.	NL4110000
F	8
HS Code	29339900
Toxizität	LD50 intraperitoneal in mouse: 176mg/kg

Gefahreninformationscode (GHS)

5-Methoxytryptamine Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R22:Gesundheitsschädlich beim Verschlucken.
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
R20/21/22:Gesundheitsschädlich beim Einatmen,Verschlucken und Berührung mit der Haut.
S-Sätze Betriebsanweisung:
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
Beschreibung
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.
Chemische Eigenschaften
White to tan crystalline powder
Verwenden
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.
Application
5-Methoxytryptamine was used as an agonist in the study of pharmacological profile of the 5-hydroxytryptamine 1 receptor.
Reactant for preparation of:
Carboline disaccharide domain of shishijimicin A
Melatonin analogs for the reduction of intraocular pressure
5-HT4 receptor ligands
inhibitors of sortase A and isocitrate lyase
Therapeutic agents for treatment of ischemia/reperfusion (I/R) injury
Aurora and epidermal growth factor receptor kinase inhibitors
Agents for the treatment of human papillomavirus infection
Manzamine analogues for the control of neuroinflammation and cerebral infections
Inhibitors of pro-inflammatory cytokines
Tacrine-melatonin hybrids as multifunctional agents for alzheimer′s disease
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+).
Allgemeine Beschreibung
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.
Synthese
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 Upstream-Materialien And Downstream Produkte

2-(5-Methoxyindol-3-yl)ethylamin Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

608-07-1, 5-Methoxytryptamine Verwandte Suche:

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