552-62-5

Basic information

• Product Name: 7-METHYLXANTHINE
• Synonyms: 3,7-dihydro-7-methyl-1h-purine-6-dione;7-methyl-xanthin;3,7-dihydro-7-methyl-1H-purine-2,6-dione;7-Methylxantine;7-METHYLXANTHINE XANTHINE DERIVATIVE;2,6-Dihydroxy-7-methylpurine, Heteroxanthine;7-methyl-3H-purine-2,6-dione;NSC 7861
• CAS NO: 552-62-5
• Molecular Formula: C6H6N4O2
• Molecular Weight: 166.14
• EINECS: 209-019-0
• Product Categories: Pyridines, Pyrimidines, Purines and Pteredines;Bases & Related Reagents;Heterocycles;Metabolites & Impurities;Nucleotides;Heterocycles, Metabolites & Impurities, Nucleotides, Bases & Related Reagents
• Mol File: 552-62-5.mol
• Article Data: 10

Chemical Properties

• Melting Point: ≥300 °C
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.83g/cm³
• Refractive Index: 1.827
• Storage Temp.: 2-8°C
• Solubility: DMSO (Slightly, Heated), Methanol (Slightly, Heated)
• PKA: pK1:8.33;pK2:ca;pK3:13 (25°C)
• Water Solubility: Soluble in dimethyl sulfoxide. Insoluble in water.
• BRN: 171027
• CAS DataBase Reference: 7-METHYLXANTHINE(CAS DataBase Reference)
• NIST Chemistry Reference: 7-METHYLXANTHINE(552-62-5)
• EPA Substance Registry System: 7-METHYLXANTHINE(552-62-5)

Safety Data

• Hazard Codes: T+
• Statements: 26/27/28
• Safety Statements: 22-24/25
• WGK Germany: 3
• RTECS: ZD8925000
• F: 10
• Hazardous Substances Data: 552-62-5(Hazardous Substances Data)

Usage

Description

7-Methylxanthine, also known as an oxopurine, is a member of the xanthine class. It is an intermediate metabolite in the synthesis of caffeine and is characterized by its grey solid appearance. 7-METHYLXANTHINE can be synthesized through the reaction between 4-amino-1-methylimidazole-5-carboxamide and diethyl carbonate. As a metabolite of theophylline and caffeine, 7-methylxanthine plays a significant role in the biochemistry of these well-known stimulants.

Uses

Used in Pharmaceutical Industry:
7-Methylxanthine is used as a building block for the synthesis of tricyclic imidazo[2,1-i]purinone derivatives, which have potential as adenosine receptor antagonists. These antagonists can be utilized in the development of medications targeting various conditions, such as asthma, chronic obstructive pulmonary disease (COPD), and other disorders where adenosine receptor modulation is beneficial.
Used in Metabolism Studies:
As a metabolite of theophylline and caffeine, 7-methylxanthine is essential in understanding the metabolic pathways and effects of these stimulants on the human body. This knowledge can be applied to optimize the use of these compounds in medical treatments and to study their potential side effects and interactions with other substances.
Used in Chemical Research:
The chemical properties of 7-methylxanthine, such as its grey solid appearance and its classification as an oxopurine, make it a valuable subject for research in the field of chemistry. Understanding its properties and reactivity can contribute to the development of new synthetic methods, potential applications, and insights into the broader class of xanthines.

InChI:InChI=1/C6H6N4O2/c1-10-2-7-4-3(10)5(11)9-6(12)8-4/h2H,1H3,(H2,8,9,11,12)

Synthetic route

2,6-dibenzyloxy-7-methylpurine (1021187-27-8) → 7-methylxanthine (552-62-5)

Conditions	Yield
With sodium hydroxide In dimethyl sulfoxide at 100℃; for 1.5h;	92%

2,6-dibenzylthio-7-methylpurine (1021187-29-0) → 7-methylxanthine (552-62-5)

Conditions	Yield
With sodium hydroxide In dimethyl sulfoxide at 100℃; for 1.5h;	90%

3-benzyl-7-methyl-1H-purine-2,6(3H,7H)-dione (64995-73-9) → 7-methylxanthine (552-62-5)

Conditions	Yield
With aluminium trichloride In toluene at 70℃; for 1h;	75%

4-amino-5-cyano-1-methyl-1H-imidazole (40637-80-7) + urethane (51-79-6) → 7-methylxanthine (552-62-5)

Conditions	Yield
at 180℃;

2,6-dichloro-7-methylpurine (2273-93-0) → 7-methylxanthine (552-62-5)

Conditions	Yield
With hydrogenchloride at 120 - 125℃;
Multi-step reaction with 2 steps 1: 80 percent / methanol / 2 h / 100 °C 2: 18percent aq. HCl / 1.5 h / Heating View Scheme
With hydrogenchloride at 120 - 125℃;

2,6-dimethoxy-7-methyl-purine (97184-74-2) → 7-methylxanthine (552-62-5)

Conditions	Yield
With hydrogenchloride for 1.5h; Heating; Yield given;

7-methyl xanthosine → 7-methylxanthine (552-62-5)

Conditions	Yield
With N-methyl nucleoside hydrolase; Tricine-NaOH buffer at 37℃; for 1h; enzymatic hydrolysis, effect of pH, temperature,metal ions and reagents on enzyme activity;

7,9-dimethylxanthinium iodide (86180-29-2) → theobromine / (83-67-0) + 7-methylxanthine (552-62-5)

Conditions	Yield
at 230℃; for 0.75h; Title compound not separated from byproducts;

7,9-dimethylxanthinium hydrogensulfate → theobromine / (83-67-0) + 7-methylxanthine (552-62-5)

Conditions	Yield
at 250℃; for 0.25h; Title compound not separated from byproducts;

7-methyl-2-hydroxy-6-methoxypurine (85982-53-2) → 7-methylxanthine (552-62-5)

Conditions	Yield
With acid

2-methoxy-6-ethoxy-7-methylpurine (97184-78-6) → 7-methylxanthine (552-62-5)

Conditions	Yield
With hydrogenchloride for 1.5h; Heating; Yield given;

7-methyl-2-chloro-6-ethoxy-purine → 7-methylxanthine (552-62-5)

Conditions	Yield
With hydrogenchloride at 100℃;

7-methyl-2-chloro-adenine → 7-methylxanthine (552-62-5)

Conditions	Yield
With hydrogenchloride at 120 - 125℃;

7-methyl-2-chloro-hypoxanthine → 7-methylxanthine (552-62-5)

Conditions	Yield
With hydrogenchloride at 120 - 125℃;

7-methyl-guanine → 7-methylxanthine (552-62-5)

Conditions	Yield
With cis-nitrous acid

8-chloro-heteroxanthine → 7-methylxanthine (552-62-5)

Conditions	Yield
With phosphonium iodide; hydrogen iodide

Diethyl carbonate (105-58-8) + 1-methyl-4-amino-imidazole-carboxylic acid-(5)-amide → 7-methylxanthine (552-62-5)

Conditions	Yield
at 160 - 170℃;

6-amino-1-benzyl-5-(methylamino)uracil (72816-88-7) → 7-methylxanthine (552-62-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: 91 percent / 12 h / Heating 2: 75 percent / AlCl3 / toluene / 1 h / 70 °C View Scheme

2-chloro-6-ethoxy-7-methylpurine (97202-78-3) → 7-methylxanthine (552-62-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: 77 percent / methanol / 2 h / 120 °C 2: 18percent aq. HCl / 1.5 h / Heating View Scheme

6-chloro-7-methyl-7H-purine (5440-17-5) → 7-methylxanthine (552-62-5)

Conditions	Yield
Multi-step reaction with 4 steps 1: methanol 2: 49 percent / 30 percent H2O2 / trifluoroacetic acid / 288 h / Ambient temperature 3: 56 percent / methanol / Irradiation 4: acid View Scheme

6-methoxy-7-methyl-7H-purine (38917-24-7) → 7-methylxanthine (552-62-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: 49 percent / 30 percent H2O2 / trifluoroacetic acid / 288 h / Ambient temperature 2: 56 percent / methanol / Irradiation 3: acid View Scheme

6-methoxy-7-methylpurine 3-oxide (85982-51-0) → 7-methylxanthine (552-62-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: 56 percent / methanol / Irradiation 2: acid View Scheme

theobromine / (83-67-0) → 7-methylxanthine (552-62-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: phosphorus oxychloride / 140 °C 2: hydrochloric acid / 120 - 125 °C View Scheme

7-methylguanine hydrochloride → 7-methylxanthine (552-62-5)

Conditions	Yield
With acetic acid; sodium nitrite

7-methylxanthine (552-62-5) + (2-trimethylethylsilylethoxy)methyl chloride (76513-69-4) → 7-methyl-3-(2-trimethylsilyl)ethoxymethylxanthine (246264-71-1)

Conditions	Yield
	69%

7-methylxanthine (552-62-5) + 1,5-dichloropentane (628-76-2) → 1,3-Bis(ω-chloropentyl)-7-methyl-xanthine (125663-73-2)

Conditions	Yield
With sodium hydroxide In N,N-dimethyl-formamide at 85 - 105℃;	68%

7-methylxanthine (552-62-5) → 7-methyl-8 nitroxanthine

Conditions	Yield
With nitronium tetrafluoborate; acetic acid at 120℃; for 1h;	38%

2-bromomethylfuran (4437-18-7) + aqueous sodium chloride + 7-methylxanthine (552-62-5) → 3-(furan-2-ylmethyl)-7-methylxanthine (301328-85-8)

Conditions	Yield
With sodium sulfate In water; dimethyl sulfoxide; ethyl acetate	14%
With sodium sulfate In water; dimethyl sulfoxide; ethyl acetate

allyl iodid (556-56-9) + 7-methylxanthine (552-62-5) → 3-allyl-7-methyl-3,7-dihydro-purine-2,6-dione (64995-72-8)

Conditions	Yield
With potassium hydroxide

7-methylxanthine (552-62-5) → 7-methyl-2-oxo-6-thioxo-1,2,3,6-tetrahydropurine (38695-88-4)

Conditions	Yield
With pyridine; tetraphosphorus decasulfide
With pyridine; tetraphosphorus decasulfide for 8h; Heating;

7-methylxanthine (552-62-5) → 2,6-dichloro-7-methylpurine (2273-93-0)

Conditions	Yield
With phosphorus pentachloride; trichlorophosphate

formaldehyd (50-00-0) + 7-methylxanthine (552-62-5) → 1,3-Bis-hydroxymethyl-7-methyl-3,7-dihydro-purine-2,6-dione

Conditions	Yield
With triethylamine In water Ambient temperature;

7-methylxanthine (552-62-5) → 7-Methyl-3,7-dihydro-purine-2,6-dione

Conditions	Yield
With azide radical In water at 25℃; Rate constant; various pH;

7-methylxanthine (552-62-5) + methyl iodide (74-88-4) + aqueous alcoholic KOH-solution → 3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione (58-08-2)

7-methylxanthine (552-62-5) + sulfuric acid (7664-93-9) + potassium permanganate → ammonia (7664-41-7) + methylamine (74-89-5)

Upstream product

• 40637-80-7 4-amino-5-cyano-1-methyl-1H-imidazole 
• 51-79-6 urethane 
• 2273-93-0 2,6-dichloro-7-methylpurine 
• 97184-74-2 2,6-dimethoxy-7-methyl-purine 
• 86180-29-2 7,9-dimethylxanthinium iodide 
• 85982-53-2 7-methyl-2-hydroxy-6-methoxypurine 
• 97184-78-6 2-methoxy-6-ethoxy-7-methylpurine 
• 105-58-8 Diethyl carbonate 
• 64995-73-9 3-benzyl-7-methyl-1H-purine-2,6(3H,7H)-dione 
• 72816-88-7 6-amino-1-benzyl-5-N-methylaminouracil 
• 97202-78-3 2-chloro-6-ethoxy-7-methylpurine 
• 5440-17-5 6-chloro-7-methyl-7H-purine 
• 38917-24-7 6-methoxy-7-methyl-7H-purine 
• 85982-51-0 6-methoxy-7-methylpurine 3-oxide 

Downstream Products

• 2273-93-0 2,6-dichloro-7-methylpurine 
• 58-08-2 3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione 
• 7664-41-7 ammonia 
• 74-89-5 methylamine 
• 57-13-6 urea 
• 107-97-1 sarcosine 
• 15719-64-9 methylammonium carbonate 
• 61066-33-9 pyrimidine-2,4,5,6(1H,3H)-tetraone 
• 598-50-5 N-Methylurea 
• 612-37-3 7-methyluric acid 
• 33403-02-0 7-methyl-2,6-dithioxo-1,2,3,6-tetrahydropurine 
• 83-67-0 theobromine / 

Relevant articles and documents

Xanthines studied via femtosecond fluorescence spectroscopy

Xanthines represent a wide class of compounds closely related to the DNA bases adenine and guanine. Ubiquitous in the human body, they are capable of replacing natural bases in double helices and give rise to four-stranded structures. Although the use of their fluorescence for analytical purposes was proposed, their fluorescence properties have not been properly characterized so far. The present paper reports the first fluorescence study of xanthine solutions relying on femtosecond spectroscopy. Initially, we focus on 3-methylxanthine, showing that this compound exhibits non-exponential fluorescence decays with no significant dependence on the emission wavelength. The fluorescence quantum yield (3 × 10-4) and average decay time (0.9 ps) are slightly larger than those found for the DNA bases. Subsequently, we compare the dynamical fluorescence properties of seven mono-, di- and tri-methylated derivatives. Both the fluorescence decays and fluorescence anisotropies vary only weakly with the site and the degree of methylation. These findings are in line with theoretical predictions suggesting the involvement of several conical intersections in the relaxation of the lowest singlet excited state.

N6-SUBSTITUTED ADENOSINE DERIVATIVES AND N6-SUBSTITUTED ADENINE DERIVATIVES AND USES THEREOF

The present invention provides N6-substituted adenosine derivatives and N6-substituted adenine derivatives, manufacturing methods thereof, a pharmaceutical composition comprising the said compounds above, and uses of these compounds in manufacturing medicaments and health-care products for treating insomnia, convulsion, epilepsy, and Parkinson's diseases, and preventing and treating dementia.

Synthesis of the azathiopurine analogs

The effective synthesis of the azathioprine analogs - 2-subsituted derivatives of 7-methyl-6-(1-methyl-4-nitroimidazol-5-ylthio)purines 5 has been achieved by the reaction of 2-subsituted 6-purinethiones 4 with 5-chloro-l-methyl-4-nitroimidazole in ethano