832-66-6

Basic information

• Product Name: 1-Methylcaffeine
• Synonyms: 1,3,7,8-TETRAMETHYL XANTHINE;1,3,7,8-Tetramethylpurine-2,6-dione;1-Methylcaffeine;1,3,6, 7-Tetramethylxanthine;METHYLCAFFEINE, 8-(P);8-Methylcaffeine
• CAS NO: 832-66-6
• Molecular Formula: C₉H₁₂N₄O₂
• Molecular Weight: 208.22
• Product Categories: Heterocycles series
• Mol File: 832-66-6.mol
• Article Data: 7

Chemical Properties

• Melting Point: 210～211℃
• Boiling Point: 347.41°C (rough estimate)
• Flash Point: 202.2 °C
• Appearance: /
• Density: 1.2480 (rough estimate)
• Vapor Pressure: 5.89E-07mmHg at 25°C
• Refractive Index: 1.6590 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• Water Solubility: 2.175g/L(20 oC)
• CAS DataBase Reference: 1-Methylcaffeine(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Methylcaffeine(832-66-6)
• EPA Substance Registry System: 1-Methylcaffeine(832-66-6)

Safety Data

• Hazardous Substances Data: 832-66-6(Hazardous Substances Data)

Usage

Active constituent of Silm FX

Known from the recipe of Silm FX, 1,3,7,8-tetramethylxanthine is one of the components. The product claims it is useful for men and women who are striving to lose weight, but frequently fall short due to tiredness and unhealthy snack cravings throughout the day. The central to successful weight loss plan is the ability to suppress your appetite, especially cravings for unhealthy carbs like sugar. Slim FX works by curbing, not eliminating appetite, so people can remain healthy by eating a small balanced diet and controlling intra-meal cravings. Take Slim FX and eat three sensible meals a day and curb the cravings for unhealthy snack foods between meals. But some data from the US Army Aberdeen Proving Grounds, the action of STIM X as well as Venom stem from an 8-substituted methylxanthine. People have mentioned the habitual use of both will really dry you out and make you cramp. Also, a rapid water loss could be mistaken for fat loss by many people. So some people think caffeine and paraxanthine are actually better fat loss agents than the 8-subbed versions.

InChI:InChI=1/C9H12N4O2/c1-5-10-7-6(11(5)2)8(14)13(4)9(15)12(7)3/h1-4H3

Upstream product

• 14173-47-8 6-amino-5-dimethylamino-1,3-dimethyl-1H-pyrimidine-2,4-dione 
• 108-24-7 acetic anhydride 
• 74-88-4 methyl iodide 
• 107-71-1 tert-butyl peroxyacetate 
• 58-08-2 3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione 
• 67-68-5 dimethyl sulfoxide 
• 25554-84-1 2-(ethoxycarbonothioylthio)acetic acid 
• 27038-96-6 1,3,8,9-tetramethylxanthine 
• 64-19-7 acetic acid 
• 110-05-4 di-tert-butyl peroxide 
• 79-20-9 acetic acid methyl ester 
• 17338-96-4 8-methylxanthine 
• 77-78-1 dimethyl sulfate 
• 74-87-3 methylene chloride 

Downstream Products

• 74-89-5 methylamine 

Relevant articles and documents

Profiling the oxidative activation of DMSO-F6 by pulse radiolysis and translational potential for radical C-H trifluoromethylation

The oxidative activation of the perfluorinated analogue of dimethyl sulfoxide, DMSO-F6, by hydroxyl radicals efficiently produces trifluoromethyl radicals based on pulse radiolysis, laboratory scale experiments, and comparison of rates of reaction for analogous radical systems. In comparison to commercially available precursors, DMSO-F6 proved to be more stable, easier to handle and overall more convenient than leading F3C-reagents and may therefore be an ideal surrogate to study F3C radicals for time-resolved kinetics studies. In addition, we present an improved protocol for the preparation of this largely unexplored reagent.

Late-stage functionalization of biologically active heterocycles through photoredox catalysis

The direct C-H functionalization of heterocycles has become an increasingly valuable tool in modern drug discovery. However, the introduction of small alkyl groups, such as methyl, by this method has not been realized in the context of complex molecule synthesis since existing methods rely on the use of strong oxidants and elevated temperatures to generate the requisite radical species. Herein, we report the use of stable organic peroxides activated by visible-light photoredox catalysis to achieve the direct methyl-, ethyl-, and cyclopropylation of a variety of biologically active heterocycles. The simple protocol, mild reaction conditions, and unique tolerability of this method make it an important tool for drug discovery.

ADDITION OF ELECTROPHILIC RADICALS TO CAFFEINE: SYNTHETIC ASPECTS AND INFLUENCE OF THE PEROXIDIC INITIATORS

Primary and secondary electrophilic radicals such as: .CHRCO2CH3 (R=H, CH3, CO2CH3) and tertiary .CCl3 radical were added directly at C-8 of, th model purine compound, caffeine to give the corresponding 8-substituted derivatives in fairly good yields.Unexpected reaction of caffeine with oxy radicals from the initiators (PhCO2., t-BuOO.) gave rise to C-5 substituted 1,3,7-trimethyl-5,7-dihydrouric acid derivatives (C-5-R=CCl3, CH3, C(CH3)2CO2CH3) and to the spirodihydantoin C-8 adduct derivative of caffeine 11.