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 |
|
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 | |
|---|---|---|---|---|---|
| Jinan Jianfeng Chemical Co., Ltd | 0531-88110457; +8615562555968 | info@pharmachemm.com | China | 246 | 58 |
| Hebei Guanlang Biotechnology Co., Ltd. | +86-19930503259 +86-19930503259 | cherry@crovellbio.com | China | 18458 | 58 |
| Firsky International Trade (Wuhan) Co., Ltd | +8615387054039 | admin@firsky-cn.com | China | 436 | 58 |
| Wuhan wingroup Pharmaceutical Co., Ltd | +86-13296627870; +8613296627870 | info@whwingroup.com | China | 703 | 58 |
| Shanghai UCHEM Inc. | +862156762820 +86-13564624040 | sales@myuchem.com | China | 6711 | 58 |
| Hebei Anlijie Biotechnology Co., Ltd | +8619031013551 | ably@aljbio.com | China | 177 | 58 |
| Wuhan Ruichi Technology Co., Ltd | +8613545065237 | admin@whrchem.com | China | 164 | 58 |
| Suzhou Sanyi Polymer Chemical Technology Co., Ltd. | +8615571922873 | 15571922873@163.com | China | 106 | 58 |
| Chongqing Zhihe Biopharmaceutical Co., Ltd. | +86-18580541567 +86-17782035140 | sales@zhswyy.com | China | 338 | 58 |
| Shaanxi Franta Biotechnology Co., Ltd | +86-13082019107 +86-13082019107 | admin@flanderff.com | China | 229 | 58 |
View Lastest Price from 5-Methoxytryptamine manufacturers
| Image | Update time | Product | Price | Min. Order | Purity | Supply Ability | Manufacturer | |
|---|---|---|---|---|---|---|---|---|
 |
2024-04-19 | 5-Methoxytryptamine
608-07-1
|
US $0.00 / Kg/Drum | 1KG | 99% | 100mt | Jinan Finer Chemical Co., Ltd | |
 |
2024-04-15 | 5-Methoxytryptamine
608-07-1
|
US $20.00 / kg | 1kg | 99 | 20 ton | Suzhou Sanyi Polymer Chemical Technology Co., Ltd. | |
 |
2024-04-12 | 5-Methoxytryptamine
608-07-1
|
US $30.00 / kg | 1kg | 98% | 2000kg | hebei hongtan Biotechnology Co., Ltd |
-
- 5-Methoxytryptamine
608-07-1
- US $0.00 / Kg/Drum
- 99%
- Jinan Finer Chemical Co., Ltd
-
- 5-Methoxytryptamine
608-07-1
- US $20.00 / kg
- 99
- Suzhou Sanyi Polymer Chemical Technology Co., Ltd.
-
- 5-Methoxytryptamine
608-07-1
- US $30.00 / kg
- 98%
- hebei hongtan Biotechnology Co., Ltd