Isocaffeine

Structural formula
General
Surname	Isocaffeine
other names	1,3,9-trimethylxanthine 2,6-dihydroxy-1,3,9-trimethylpurine 1,3,9-trimethyl-2,6-dioxypurine
Molecular formula	C 8 H 10 N 4 O 2
Brief description	colorless solid
External identifiers / databases
CAS number 519-32-4 EC number 208-267-7 ECHA InfoCard 100.007.517 PubChem 1326 Wikidata Q1674397
properties
Molar mass	194.19 g mol −1
Physical state	firmly
Melting point	286 ° C (decomposition)
safety instructions
GHS labeling of hazardous substances no GHS pictograms H and P phrases H: no H-phrases P: no P-phrases
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Isocaffeine (1,3,9-trimethylxanthine) is a chemical compound which differs from caffeine (1,3,7-trimethylxanthine) only in the position of a methyl group . This changes the external structure of the molecule and the pharmacological effect is therefore significantly different from that of caffeine.

Isocaffeine has a much weaker effect, the muscle rigidity remains and the tetanic phenomena take a back seat to the paralysis. In contrast to caffeine, isocaffeine has only a weak diuretic effect .

It is an adenosine receptor antagonist .

properties

Isocaffeine crystallizes in the monoclinic crystal system in the space group P 2 ₁ / n (space group no. 14, position 2) with the lattice parameters a = 771.7  pm , b = 791.5 pm, c = 1364.6 pm and β = 92 , 86 °. In the unit cell contains four formula units .

literature

• B. FRÄNKEL: "The drug synthesis based on the relationships between chemical structure and effect" , FIFTH, REVISED EDITION, BERLIN, PUBLISHING JULIUS SPRINGER 1921

Individual evidence

1. ↑ ^{a b c d} data sheet 1,3,9-trimethylxanthine from Sigma-Aldrich , accessed on May 11, 2011 ( PDF ).
2. ^ H. Rasmussen, E. Sletten: "The Crystal and Electronic Structure of Isocaffeine, (1,3,9-Trimethyl-2,6-dioxypurine)" , in: Acta Chem. Scand. , 1973 , 27 , pp. 2757-2768. (PDF; 1.1 MB)