5426-47-1

Usage

Chemical compound

8-Dimethylaminotheophylline (8-DMAT)

Also known as

8-DMAT

Primary use

Pharmacological research

Derivative of

Theophylline

Type

Methylxanthine derivative

Actions

Phosphodiesterase inhibitor and adenosine receptor antagonist

Studied for potential therapeutic effects on

Asthma, chronic obstructive pulmonary disease (COPD), and other respiratory disorders

Investigated for potential role in

Enhancing cognitive function and memory

Ability

Crosses the blood-brain barrier

Potential for

Treatments related to central nervous system disorders

Additional notes

Further research needed to fully understand pharmacological effects and potential applications

InChI:InChI=1/C9H13N5O2/c1-12(2)8-10-5-6(11-8)13(3)9(16)14(4)7(5)15/h1-4H3,(H,10,11)

Upstream product

• 120788-57-0 6-<<(dimethylamino)methylene>amino>-5-(3,5-dioxo-4-phenyl-1,2,4-triazolin-1-yl)-1,3-dimethyluracil 
• 5440-00-6 4,5-Diamino-1,3-dimethyluracil 
• 33842-02-3 dichloromethylenedimethyliminium chloride 
• 10381-75-6 8-bromotheophylline 
• 124-40-3 dimethyl amine 
• 6642-31-5 6-Amino-1,3-dimethylbarbituric acid 
• 120788-53-6 6-<(dimethylamino)methylene>amino-1,3-dimethyluracil 
• 120788-53-6 6-<<(dimethylamino)methylene>amino>-1,3-dimethyluracil 
• 483-57-8 fervenulin 
• 40011-95-8 fervenulin-1-oxide 
• 77012-46-5 chlorure d'amino-4 (chloromethine N-dimethyl iminium)-5 dimethyl-1,3 uracile 
• 120788-72-9 5-<1,2-bis(ethoxycarbonyl)hydrazino>-6-<<(dimethylamino)methylene>amino>-1,3-dimethyluracil 
• 120788-73-0 5-<1,2-bis(phenoxycarbonyl)hydrazino>-6-<<(dimethylamino)methylene>amino>-1,3-dimethyluracil 

Downstream Products

• 148122-89-8 7-p-dimethylaminobenzoyl-8-dimethylaminotheophylline 
• 148122-87-6 7-benzoyl-8-dimethylaminotheophylline 
• 148122-88-7 7-p-nitrobenzoyl-8-dimethylaminotheophylline 
• 78146-62-0 7-methyl-8-dimethylaminotheophylline 

Relevant academic research and scientific papers

Purines, Pyrimidines, and Condensed Systems Based on These Compounds. 13. Transformation of Fervenulin-1-oxide to 8-Alkylaminotheophyllines Under the Action of Alkylamines

Fervenulin-1-oxide undergoes reactions with secondary alkylamines in which the triazine ring is ruptured and 8-alkylaminotheophyllines are formed.The final product of the interaction of fervenulin-1-oxide with primary amines or with liquid ammonia is 1,3-dimethyl-5-imino-6-hydroximinouracil.

A new entry to the imidazo[4,5-d]pyrimidine system. The reaction of 1,3-dimethyl-6-aminouracil with N,N-dimethyldichloromethyleniminium chloride (phosgeniminium chloride) and trimethylsilyl azide

1,3-Dimethyl-6-aminouracil 2 was converted into various 8-N-arylaminotheophyllines (2-N-arylamino-4,6-dimethylimidazo[4,5-d]pyrimidine-(4H,6H)-5,7-diones ) 17 through reaction successively, with phosgeniminium chloride (N,N-dimethyldichloromethyleniminium chloride) (1a), trimethylsilyl azide (4) and arylamines. Starting with the synthesis of the N,N-dimethyl-(1,3-dimethyl-4-aminouracil-5 yl)chloromethyleniminiun chloride (amide chloride) 3 this new route to the imidazo[4,5-d]pyrimidine skeleton was shown to proceed via the formation of a very unstable N,N-dimethyl-(1,3-dimethyl-4-aminouracil-5-yl)azidomethyleniminium chloride (amide azide) (8) which would undergo an in situ rearrangement into very likely, a 4-amino-5-(chloroformamidin-1'-yl)uracil and/or related compounds of types 10. Depending on reaction conditions, the latter was proved to be a very good precursor of the 8-dimethylaminotheophylline 11 as well.

Reactions of Uracils, 16. - Substituted 6-Vinyl-2,4(1H,3H)-pyrimidinediones in Cycloaddition and Michael-Type Reactions: Pyridopyrimidines, Pyrrolopyridines, and Quinazolines

Electron-rich 6-vinyl- and 6-(azavinyl)pyrimidinediones, such as 6-amino>- (1) and 6--1,3-dimethyl-2,4(1H,3H)-pyrimidinediones (8), undergo cycloaddition reactions with electron deficient olefins to give pyridopyrimidines (3a-e) and quinazolines (9a-c), respectively, after elimination of dimethylamine from the 1:1 cycloadducts and oxidative aromatization.With dimethyl acetylenedicarboxylate, pyrrolopyridines 5, 11, and 15 were obtained due to an initial Michael addition and subsequent ring transformation reaction.Stable Michael adducts were also obtained from reactions of 1 with azodicarboxylates.The stable adducts 6a-c were thermally converted into 8-(dimethylamino)theophylline (7). - Key Words: Pyridopyrimidines/ Pyrrolopyridines/ Quinazolines/ 6-Vinyl-2,4(1H,3H)-pyrimidinediones/ Cycloaddition

6-AMINO-1,3-DIMETHYLURACIL: A VERSATILE AZA-DIENE SUBSTRATE FOR CYCLOADDITION AND MICHAEL-TYPE REACTIONS

6-amino-1,3-dimethyluracil 1 undergoes formal cycloaddition reactions with electron deficient olefins to give pyridopyrimidines.With DMAD or azodicarboxylates Michael addition occurs leading to pyrrolopyridines (X-ray analysis) and theophylline derivatives.