5-Methoxytryptamine
- CAS No.
- 608-07-1
- Chemical Name:
- 5-Methoxytryptamine
- Synonyms
- 5-Methoxyindoleacetate;2-(5-METHOXY-1H-INDOL-3-YL)ETHANAMINE;2-(5-methoxy-1H-indol-3-yl)acetic acid;Methoxytryptamine;MEXAMINE;O-METHYLSEROTONIN;Melatonin Related CoMpound A;MEXAMINE HYDROCHLORIDE;5-METHOXYTRYPTAMINE HCL;5-methoxy-1h-indole-3-ethanamin
- CBNumber:
- CB0676885
- Molecular Formula:
- C11H14N2O
- Molecular Weight:
- 190.24
- MDL Number:
- MFCD00005662
- MOL File:
- 608-07-1.mol
- MSDS File:
- SDS
- TDS File:
- TDS
| 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) |
| UNSPSC Code | 41116107 |
| NACRES | NA.24 |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |  GHS07 |
|||||||||
|---|---|---|---|---|---|---|---|---|---|---|
| Signal word | Warning | |||||||||
| Hazard statements | H302 | |||||||||
| Precautionary statements | P301+P312+P330 | |||||||||
| PPE | dust mask type N95 (US), Eyeshields, Gloves | |||||||||
| 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 | |||||||||
| Storage Class | 11 - Combustible Solids | |||||||||
| Hazard Classifications | Acute Tox. 4 Oral | |||||||||
| Toxicity | LD50 intraperitoneal in mouse: 176mg/kg | |||||||||
| REACH Registrations | Active | |||||||||
| NFPA 704 |
|
5-Methoxytryptamine price More Price(59)
| 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 | $623 | 2026-04-30 | Buy |
| Sigma-Aldrich | 286583 | 5-Methoxytryptamine 97% | 608-07-1 | 1g | $80 | 2026-04-30 | Buy |
| Sigma-Aldrich | 1380116 | Melatonin Related Compound A United States Pharmacopeia (USP) Reference Standard | 608-07-1 | 15mg | $1260 | 2026-04-30 | Buy |
| TCI Chemical | M0131 | 5-Methoxytryptamine | 608-07-1 | 1g | $46 | 2026-04-30 | Buy |
| TCI Chemical | M0131 | 5-Methoxytryptamine | 608-07-1 | 5g | $184 | 2026-04-30 | 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.
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
| Supplier | Tel | Country | ProdList | Advantage | |
|---|---|---|---|---|---|
| Qi Qi hang Biotechnology Co., Ltd. | 18151111370 | 1046215251@qq.com | China | 5999 | 58 |
| Hefei Chaobo Technology Co., Ltd | 19322001459 | zb19922001456@163.com | China | 438 | 58 |
| Shanghai Guoyuan Chemical Co., Ltd. | 0512-55170668; 13913095008 | shgyhg@139.com | China | 486 | 58 |
| Huanggang Saikang Pharmaceutical Co.,Ltd | -- | hgsaikang@163.com | China | 11 | 58 |
| Hubei Xingyao Biomedical Technology Co., Ltd | 17871673970 | 63857756@qq.com | China | 4995 | 58 |
| Hubei Hengluyuan Technology co.ltd | 027-88188016 18717196322 | 1764683941@qq.com | China | 5944 | 58 |
| Hubei Hanqing Biopharmaceutical Technology Co., Ltd | 15827479330 | 3583890861@qq.com | China | 4992 | 58 |
| J & K SCIENTIFIC LTD. | 18210857532 18210857532 | jkinfo@jkchemical.com | China | 96815 | 76 |
| Meryer (Shanghai) Chemical Technology Co., Ltd. | 4006356688 18621169109 | market03@meryer.com | China | 40202 | 62 |
| 3B Pharmachem (Wuhan) International Co.,Ltd. | 18930552037 | 3bsc@sina.com | China | 15813 | 69 |
Related articles
- The biosynthesis and physiological distribution of 5-methoxytryptamine
- 5-Methoxytryptamine is a potent antioxidant. This article mainly introduces its biosynthetic methods and physiological distrib....
- May 7,2025
View Latest Price from 5-Methoxytryptamine manufacturers
| Image | Update time | Product | Price | Min. Order | Purity | Supply Ability | Manufacturer | |
|---|---|---|---|---|---|---|---|---|
 |
2026-09-16 | 5-Methoxytryptamine
608-07-1
|
$1.00 | 1g | 99% | 100kg | RongNa Biotechnology Co.,Ltd | |
 |
2026-09-16 | 5-Methoxytryptamine
608-07-1
|
$49.00-222.00 | 100g | 0.98 | 25kg | Shanghai UCHEM Inc. | |
 |
2026-08-26 | 5-Methoxytryptamine
608-07-1
|
1kg | 99% | 99999 | Rongchuang International |
-
- 5-Methoxytryptamine
608-07-1
- $1.00
- 99%
- RongNa Biotechnology Co.,Ltd
-
- 5-Methoxytryptamine
608-07-1
- $49.00-222.00
- 0.98
- Shanghai UCHEM Inc.
-
- 5-Methoxytryptamine
608-07-1
- $0.00
- 99%
- Rongchuang International
