5-Methoxytryptamine
- CAS No.
- 608-07-1
- Chemical Name:
- 5-Methoxytryptamine
- Synonyms
- 5-Methoxyindoleacetate;Methoxytryptamine;2-(5-METHOXY-1H-INDOL-3-YL)ETHANAMINE;Melatonin Related CoMpound A;2-(5-methoxy-1H-indol-3-yl)acetic acid;MEXAMINE;MEXAMINE HYDROCHLORIDE;5-METHOXYTRYPTAMINE HCL;2-(5-methoxyindol-3-yl)ethylamine;5MOT
- CBNumber:
- CB0676885
- Molecular Formula:
- C11H14N2O
- Molecular Weight:
- 190.24
- MDL Number:
- MFCD00005662
- MOL File:
- 608-07-1.mol
- MSDS File:
- SDS
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) |
form | crystalline |
pka | 16.91±0.30(Predicted) |
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) |
EWG's Food Scores | 1 |
FDA UNII | 3VMW6141KC |
NIST Chemistry Reference | 5-Methoxytryptamine(608-07-1) |
SAFETY
Risk and Safety Statements
Symbol(GHS) | GHS07 |
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Signal word | Warning | |||||||||
Hazard statements | H302 | |||||||||
Precautionary statements | P301+P312+P330 | |||||||||
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 | |||||||||
NFPA 704 |
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5-Methoxytryptamine price More Price(25)
Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
---|---|---|---|---|---|---|---|
Sigma-Aldrich | PHR2241 | Melatonin Related Compound A Pharmaceutical Secondary Standard; Certified Reference Material | 608-07-1 | 50mg | $535 | 2024-03-01 | Buy |
Sigma-Aldrich | 286583 | 5-Methoxytryptamine 97% | 608-07-1 | 1g | $72.9 | 2024-03-01 | Buy |
Sigma-Aldrich | 1380116 | Melatonin Related Compound A United States Pharmacopeia (USP) Reference Standard | 608-07-1 | 15mg | $1310 | 2024-03-01 | Buy |
TCI Chemical | M0131 | 5-Methoxytryptamine | 608-07-1 | 1g | $46 | 2024-03-01 | Buy |
TCI Chemical | M0131 | 5-Methoxytryptamine | 608-07-1 | 5g | $184 | 2024-03-01 | Buy |
5-Methoxytryptamine Chemical Properties,Uses,Production
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.
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+).
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
Supplier | Tel | Country | ProdList | Advantage | |
---|---|---|---|---|---|
Hebei Guanlang Biotechnology Co., Ltd. | +8619930503259 | cherry@crovellbio.com | China | 18419 | 58 |
Firsky International Trade (Wuhan) Co., Ltd | +8615387054039 | admin@firsky-cn.com | China | 436 | 58 |
Shanghai UCHEM Inc. | +862156762820 +86-13564624040 | sales@myuchem.com | China | 7192 | 58 |
Wuhan Ruichi Technology Co., Ltd | +8613545065237 | admin@whrchem.com | China | 161 | 58 |
Dorne Chemical Technology co. LTD | +86-86-13583358881 +8618560316533 | Ethan@dornechem.com | China | 3128 | 58 |
Hebei Chuanghai Biotechnology Co,.LTD | +86-13131129325 | sales1@chuanghaibio.com | China | 5895 | 58 |
Hebei Fengjia New Material Co., Ltd | +86-0311-87836622 +86-17333973358 | sales06@hbduling.cn | China | 8054 | 58 |
Suzhou Sanyi Polymer Chemical Technology Co., Ltd. | +8615571922873 | 15571922873@163.com | China | 106 | 58 |
Shaanxi Franta Biotechnology Co., Ltd | +86-13082019107 +86-13082019107 | admin@flanderff.com | China | 208 | 58 |
Shandong Juchuang Chemical Co., LTD | +undefined15030412209 | admin@juchuangchem.com | China | 387 | 58 |
View Lastest Price from 5-Methoxytryptamine manufacturers
Image | Update time | Product | Price | Min. Order | Purity | Supply Ability | Manufacturer | |
---|---|---|---|---|---|---|---|---|
2024-10-02 | 5-Methoxytryptamine
608-07-1
|
US $1.00 / g | 1g | 99% | 100kg | Dorne Chemical Technology co. LTD | ||
2024-09-30 | 5-Methoxytryptamine
608-07-1
|
US $0.00 / Kg/Drum | 1KG | 99% | 100mt | Jinan Finer Chemical Co., Ltd | ||
2024-09-30 | 5-Methoxytryptamine
608-07-1
|
US $30.00 / kg | 1kg | 98% | 2000kg | hebei hongtan Biotechnology Co., Ltd |
- 5-Methoxytryptamine
608-07-1
- US $1.00 / g
- 99%
- Dorne Chemical Technology co. LTD
- 5-Methoxytryptamine
608-07-1
- US $0.00 / Kg/Drum
- 99%
- Jinan Finer Chemical Co., Ltd
- 5-Methoxytryptamine
608-07-1
- US $30.00 / kg
- 98%
- hebei hongtan Biotechnology Co., Ltd