1010-95-3

Basic information

• Product Name: 5-Methyltryptamine hydrochloride
• Synonyms: 2-(5-METHYL-1H-INDOL-3-YL)ETHYLAMINE HYDROCHLORIDE;2-(5-METHYL-1H-INDOL-3-YL)ETHANAMINE HYDROCHLORIDE;2-[5-METHYLINDOL-3-YL]ETHYLAMINE HYDROCHLORIDE;3-(2-AMINOETHYL)-5-METHYLINDOLE HYDROCHLORIDE;3-(2-AMINOETHYL)-5-METHYLINDOLE HCL;5-METHYLTRYPTAMINE HCL;5-METHYLTRYPTAMINE HYDROCHLORIDE;TIMTEC-BB SBB003440
• CAS NO: 1010-95-3
• Molecular Formula: C₁₁H₁₄N₂*ClH
• Molecular Weight: 210.7
• EINECS: 213-777-8
• Mol File: 1010-95-3.mol
• Article Data: 3

Chemical Properties

• Melting Point: 290-292 °C
• Boiling Point: 355.3°Cat760mmHg
• Flash Point: 195.9°C
• Appearance: /
• Density: 1.126g/cm³
• Vapor Pressure: 3.16E-05mmHg at 25°C
• Sensitive: Hygroscopic
• CAS DataBase Reference: 5-Methyltryptamine hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Methyltryptamine hydrochloride(1010-95-3)
• EPA Substance Registry System: 5-Methyltryptamine hydrochloride(1010-95-3)

Safety Data

• Hazard Codes: T+
• Statements: 26/27/28
• Safety Statements: 22-24/25
• RIDADR: 2811
• WGK Germany: 3
• F: 10
• HazardClass: 6.1
• PackingGroup: Ⅲ
• Hazardous Substances Data: 1010-95-3(Hazardous Substances Data)

Usage

Description

5-Methyltryptamine hydrochloride is a methylated derivative of tryptamine, which is a weak antagonist of 5-Hydroxytryptamine (H974990). It exhibits weak potency as a stimulant of the cardiac sympathetic nerves and is characterized by its light tan solid appearance.

Uses

Used in Pharmaceutical Industry:
5-Methyltryptamine hydrochloride is used as a reactant for the synthesis of kinesin spindle protein (KSP) inhibitors, which are a promising class of anticancer agents. These inhibitors have the potential to target and disrupt the function of KSP, a motor protein involved in cell division, thereby inhibiting cancer cell growth.
Used in Chemical Synthesis:
5-Methyltryptamine hydrochloride serves as a reactant in intramolecular furan Diels-Alder reactions, which are important synthetic processes in organic chemistry. These reactions involve the formation of a cyclic compound from a furan-containing molecule, and the use of 5-Methyltryptamine hydrochloride as a reactant can lead to the creation of novel and complex molecular structures.
Used in Organic Chemistry:
5-Methyltryptamine hydrochloride is also used as a reactant in Pictet-Spengler-like reactions, which are a type of organic reaction that involves the formation of a cyclic compound from an amine and an aldehyde or ketone. These reactions are widely used in the synthesis of various natural products and pharmaceutical compounds, and the use of 5-Methyltryptamine hydrochloride as a reactant can contribute to the development of new and innovative chemical entities.

Purification Methods

Recrystallise the hydrochloride from H2O. The free base has m 96-98o (from *C6H6/cyclohexane) or m 99-100o (from pet ether), and the picrate has m 243o(dec) (from EtOH). [Young J Chem Soc 3493 1958, Gaddum et al. Quart J Exp Physiol 40 49 1955, R.hm Hoppe Seyler's Z Physiol Chem 297 229 1954, Beilstein 22 III/IV 4364, 22/10 V 167.]

InChI:InChI=1/C11H14N2.ClH/c1-8-2-3-11-10(6-8)9(4-5-12)7-13-11;/h2-3,6-7,13H,4-5,12H2,1H3;1H

Upstream product

• 104510-00-1 3-(2-amino-ethyl)-5-methyl-indole-2-carboxylic acid 
• 3464-82-2 6-methyl-2,3,4,9-tetrahydro-β-carbolin-1-one 
• 6346-09-4 4-aminobutyrylaldehyde diethylacetal 
• 637-60-5 p-tolylhydrazine hydrochloride 
• 54322-20-2 4-chloro-1-hydroxy-1-butanesulfonate sodium 

Downstream Products

• 174727-68-5 2-[1-(2,5-Dimethyl-benzyl)-5-methyl-1H-indol-3-yl]-ethylamine 
• 172895-15-7 LY 272015 
• 172895-39-5 6-methyl-1-[(2-chloro-3,4-dimethoxyphenyl)-methyl]-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole hydrochloride 

Relevant articles and documents

Temozolomide analogs with improved brain/plasma ratios – Exploring the possibility of enhancing the therapeutic index of temozolomide

Temozolomide is a chemotherapeutic agent that is used in the treatment of glioblastoma and other malignant gliomas. It acts through DNA alkylation, but treatment is limited by its systemic toxicity and neutralization of DNA alkylation by upregulation of the O6-methylguanine-DNA methyltransferase gene. Both of these limiting factors can be addressed by achieving higher concentrations of TMZ in the brain. Our research has led to the discovery of new analogs of temozolomide with improved brain:plasma ratios when dosed in vivo in rats. These compounds are imidazotetrazine analogs, expected to act through the same mechanism as temozolomide. With reduced systemic exposure, these new agents have the potential to improve efficacy and therapeutic index in the treatment of glioblastoma.

N6-Substituted Adenosine Receptor Agonists. Synthesis and Pharmacological Activity as Potent Antinociceptive Agents

Novel N6-(indol-3-yl)alkyl derivatives of adenosine were synthesized.The adenosine receptor affinity and the antinociceptive activity of these compounds were assessed in binding studies and the phenylbenzoquinone-induced writhing test.Most of these analogues exhibited a potent analgesic activity without side effects.Among them, compound 3c (UP 202-32) bound to A1 (Ki = 110 nM) and A2 (Ki = 350 nM) adenosine receptors in a specific manner since it did not interact with many other receptors, especially opioid binding sites.The antinociceptive activity in the phenylbenzoquinone assay (ED50 = 3.3 mg/kg po) was antagonized by 8-cyclopentyltheophylline, suggesting that an adenosinergic mechanism underlies the analgesic activity observed with this compound.The data obtained with these new N6-substituted adenosine receptor agonists emphasize the interest of such compounds in the treatment of pain.