ChemicalBook >> CAS DataBase List >>5-Methoxytryptamine

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
Modify Date:2022-11-11 11:01:00

5-Methoxytryptamine 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)
form crystalline
pka 16.91±0.30(Predicted)
color white
Merck 13,6032
BRN 145587
InChIKey JTEJPPKMYBDEMY-UHFFFAOYSA-N
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
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
8
HS Code  29339900
Toxicity LD50 intraperitoneal in mouse: 176mg/kg

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 $467 2022-05-15 Buy
Sigma-Aldrich 286583 5-Methoxytryptamine 97% 608-07-1 1g $64.7 2022-05-15 Buy
Sigma-Aldrich 1380116 Melatonin Related Compound A United States Pharmacopeia (USP) Reference Standard 608-07-1 15mg $1200 2022-05-15 Buy
TCI Chemical M0131 5-Methoxytryptamine 608-07-1 1g $42 2022-04-27 Buy
TCI Chemical M0131 5-Methoxytryptamine 608-07-1 5g $168 2022-04-27 Buy
Product number Packaging Price Buy
PHR2241 50mg $467 Buy
286583 1g $64.7 Buy
1380116 15mg $1200 Buy
M0131 1g $42 Buy
M0131 5g $168 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.
synthesis of 5-Methoxytryptamine

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

Global( 409)Suppliers
Supplier Tel Email Country ProdList Advantage
Jinan Jianfeng Chemical Co., Ltd
+8615562555968 info@pharmachemm.com China 233 58
Hebei Guanlang Biotechnology Co., Ltd.
+86-19930503283 +86-19930503283 Linda@crovellbio.com China 2460 58
Wuhan wingroup Pharmaceutical Co., Ltd
+8613296627870 admin@whwingroup.com China 810 58
Henan DaKen Chemical CO.,LTD.
+86-371-66670886 info@dakenchem.com China 16932 58
Henan Tianfu Chemical Co.,Ltd.
+86-0371-55170693 +86-19937530512 info@tianfuchem.com China 21975 55
Hangzhou FandaChem Co.,Ltd.
+8615858145714 fandachem@gmail.com China 9377 55
Rixing Chemical CO.,LTD
+86-852-27935511 +86-86-13237129059 sales@rixingchemi.com CHINA 229 55
ATK CHEMICAL COMPANY LIMITED
21-51619050 ivan@atkchemical.com China 31212 60
Hefei TNJ Chemical Industry Co.,Ltd.
0551-65418679 info@tnjchem.com China 2990 55
career henan chemical co
+86-0371-86658258 sales@coreychem.com China 29922 58

View Lastest Price from 5-Methoxytryptamine manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
2022-11-24 5-Methoxytryptamine
608-07-1
US $0.00 / Kg/Drum 1KG 99% 100mt Jinan Finer Chemical Co., Ltd
2022-10-25 5-Methoxytryptamine
608-07-1
US $9.90 / kg 1kg 99% 200mt/month Hebei Duling International Trade Co. LTD
2022-09-30 5-Methoxytryptamine
608-07-1
US $30.00 / KG 1KG 99% 20T Hubei Amarvel Biotech Co.,Ltd.
1H-Indole-3-ethanamine, 5-methoxy- 3-(2-aminoethyl)-5-methoxy-indol 5-methoxy-1h-indole-3-ethanamin 5MOT Ethanamine,2-(5-methoxy-3-indolyl)- Indole, 3-(2-aminoethyl)-5-methoxy- Meksamin (free base) Mexamine base ART-CHEM-BB B028531 AURORA KA-7772 BIO-FARMA BF000967 METHOXYTRYPTAMINE, 5- 5-METHOXYTRYPTAMINE FREE BASE 5-METHOXY-TRYPTAMIN 2-[5-(Methyloxy)-1H-indol-3-yl]ethanaMine 3-(2-Aminoethyl)-5-methoxyindole O-Methylserotonin TIMTEC-BB SBB003309 RARECHEM AL BW 2333 O-METHYLSEROTONIN O-METHYLSEROTONIN HYDROCHLORIDE 5 - Methoxyl priMary aMine 5-METHOXYTRYPTAMINE AKOS JY2083095 AKOS B028531 AKOS BB-5620 2-[5-METHOXYINDOL-3-YL]ETHYLAMINE HYDROCHLORIDE 2-(5-METHOXY-1H-INDOL-3-YL)ETHANAMINE HYDROCHLORIDE 2-(5-METHOXY-1H-INDOL-3-YL)-ETHYLAMINE 3-(2-AMINOETHYL)-5-METHOXYINDOLE 5-METHOXYTRYPTAMINE 98+% Methyl sulfone(MSM) 3-(2-Aminoethyl)-5-methoxyindole, 5-Methoxytryptamine, Mexamine 5-Methoxy-1H-indole-3-ethan-1-amine 5-METHOXYTRYPTAMINE(5MeOTry) 5-Methoxytryptamine,97% 3-(Aminoethyl)-5-methoxyindole 5-Methoxy-[1H]-indole-3-ethanamine Meksamin 5-Methoxyindole-3-ethanamine NSC 56422 2-(5-methoxy-1H-indol-3-yl)ethanamine(SALTDATA: HCl) 5-MethyltrptaMine 2-(5-Methoxy-1H-indol-3-yl)ethylamine, 5-Methoxytryptamine 3-(2-Aminoethyl)-5-methoxy-1H-indole Melatonin Related Compound A (15 mg) (2-(5-methoxy-1H-indol-3-yl)ethanamine) Deacetylmelatonin EOS-62441 2-(5-Methoxy-1H-indol-3-yl)ethanami 5-Methoxy-3-indoleaceate Melatonin USP Related Compound A Melatonin USP RC A Melatonin Impurity 1 (Melatonin USP Related Compound A) 5-Methoxytryptamine fandachem 5-Methoxytryptamine ISO 9001:2015 REACH Melatonin Related Compound A (N-Desacetyl Melatonin/ 5-Methoxytryptamine) Melatonin Related Compound A (2-(5-methoxy-1H-indol-3-yl)ethanamine) (1380116) Methoxytryptamine 2-(5-methoxyindol-3-yl)ethylamine