3-isobutyl-1-methylxanthine

Structural formula
General
Surname	3-isobutyl-1-methylxanthine
other names	3-isobutyl-1-methyl-3,7-dihydro-1 H -purine-2,6-dione ( IUPAC ) ; IBMX;
Molecular formula	C 11 H 13 N 4 O 2
Brief description	white to beige solid
External identifiers / databases
EC number	249-259-3
ECHA InfoCard	100,044,767
PubChem	3758
ChemSpider	3627
DrugBank	DB07954
Wikidata	Q223093
properties
Molar mass	222.25 g mol −1
Physical state	firmly
Melting point	201 ° C
safety instructions
GHS labeling of hazardous substances Caution
H and P phrases	H: 302
	P: no P-phrases
Toxicological data	44 mg kg −1 ( LD 50 , mouse , ip )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

3-Isobutyl-1-methylxanthine , IBMX for short , is a heterocyclic compound from the group of xanthine derivatives or purine alkaloids , which is very similar to caffeine .

Properties and use

IBMX is a colorless solid that dissolves well in ethanol , DMSO and water with a basic pH value, but poorly in pure water. The substance decomposes in solution or when heated and must therefore be stored at temperatures below 5 ° C. IBMX is used in biology for the detection of phosphodiesterase ( PDE ), since the activity of cAMP- PDE is inhibited by this molecule.

safety instructions

IBMX is flammable, which can produce carbon monoxide and nitrogen oxides . In 7-10 day old rats, administration of IBMX produced a reduction in learning ability and behavioral problems. The substance was found to be toxic in mice; the LD ₅₀ value after intraperitoneal intake was 44 mg / kg body weight. It is therefore about four times more toxic to mice than the related caffeine (168 mg / kg).

Individual evidence

↑ Data sheet 3-isobutyl-1-methylxanthine from Acros, accessed on February 20, 2010.
↑ ^a ^b ^c ^d ^e data sheet 3-Isobutyl-1-methylxanthine from Sigma-Aldrich , accessed on March 18, 2011 ( PDF ).
↑ Caffeine derivatives on Erowid .
↑ ^a ^b Material data on IBMX at Applicher .
^ S. Gangolli (Ed.): The Dictionary of Substances and Their Effects. Volume 3 2nd edition, Royal Society of Chemistry, 1999, ISBN 978-0-85404-818-2 , p. 830.
^ BS Neal: Psychopharmacology. Berlin, 1991, 103 (3), pp. 388-397.
↑ European Journal of Medicinal Chemistry , 1990, Vol. 25, p. 653.
↑ Chemical & Pharmaceutical Bulletin , 1974, Vol. 22, p. 1459.

[1] Data sheet 3-isobutyl-1-methylxanthine from Acros, accessed on February 20, 2010.

[Sigma-2] ↑ ^a ^b ^c ^d ^e data sheet 3-Isobutyl-1-methylxanthine from Sigma-Aldrich , accessed on March 18, 2011 ( PDF ).

[3] Caffeine derivatives on Erowid .

[Applichem-4] Material data on IBMX at Applicher .

[5] S. Gangolli (Ed.): The Dictionary of Substances and Their Effects. Volume 3 2nd edition, Royal Society of Chemistry, 1999, ISBN 978-0-85404-818-2 , p. 830.

[6] BS Neal: Psychopharmacology. Berlin, 1991, 103 (3), pp. 388-397.

[7] European Journal of Medicinal Chemistry , 1990, Vol. 25, p. 653.

[8] Chemical & Pharmaceutical Bulletin , 1974, Vol. 22, p. 1459.