5-Methoxytryptamine
- Product Name
- 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
- Formula Weight
- 190.24
- MOL File
- 608-07-1.mol
5-Methoxytryptamine Property
- 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)
Safety
- 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
N-Bromosuccinimide Price
- Product number
- PHR2241
- Product name
- Melatonin Related Compound A
- Purity
- Pharmaceutical Secondary Standard; Certified Reference Material
- Packaging
- 50mg
- Price
- $535
- Updated
- 2024/03/01
- Product number
- 286583
- Product name
- 5-Methoxytryptamine
- Purity
- 97%
- Packaging
- 1g
- Price
- $72.9
- Updated
- 2024/03/01
- Product number
- 1380116
- Product name
- Melatonin Related Compound A
- Purity
- United States Pharmacopeia (USP) Reference Standard
- Packaging
- 15mg
- Price
- $1310
- Updated
- 2024/03/01
- Product number
- M0131
- Product name
- 5-Methoxytryptamine
- Packaging
- 1g
- Price
- $46
- Updated
- 2024/03/01
- Product number
- M0131
- Product name
- 5-Methoxytryptamine
- Packaging
- 5g
- Price
- $184
- Updated
- 2024/03/01
5-Methoxytryptamine Chemical Properties,Usage,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.
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.
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
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
Raw materials
Preparation Products
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View Lastest Price from 5-Methoxytryptamine manufacturers
- Product
- 5-Methoxytryptamine 608-07-1
- Price
- US $1.00/g
- Min. Order
- 1g
- Purity
- 99%
- Supply Ability
- 100kg
- Release date
- 2024-05-28
- Product
- 5-Methoxytryptamine 608-07-1
- Price
- US $99.00-35.00/kg
- Min. Order
- 1kg
- Purity
- 99%
- Supply Ability
- 20ton
- Release date
- 2024-05-08
- Product
- 5-Methoxytryptamine 608-07-1
- Price
- US $79.00-38.00/kg
- Min. Order
- 1kg
- Purity
- 99%
- Supply Ability
- 20ton
- Release date
- 2024-11-13