Caffeine (data page)

Caffeine
Properties
Chemical formula	C8H10N4O2
Molar mass	194.194 g·mol−1
Appearance	Odorless, white needles or powder
Density	1.23 g/cm3, solid
Melting point	227 to 228 °C (441 to 442 °F; 500 to 501 K) (anhydrous); 234 to 235 °C (453 to 455 °F; 507 to 508 K) (monohydrate)
Boiling point	178 °C (352 °F; 451 K) (sublimation)
Solubility in water	2.17 g/100 mL (25 °C); 18.0 g/100 mL (80 °C); 67.0 g/100 mL (100 °C)
Acidity (pKa)	−0.13–1.22
Dipole moment	3.64 D (calculated)

Caffeine
Identifiers
CAS Number	58-08-2 ;
3D model (JSmol)	Interactive image; Interactive image;
Beilstein Reference	17705
ChEBI	CHEBI:27732 ;
ChEMBL	ChEMBL113 ;
ChemSpider	2424 ;
DrugBank	DB00201 ;
EC Number	200-362-1;
Gmelin Reference	103040
IUPHAR/BPS	407;
KEGG	D00528 ;
PubChem CID	2519;
RTECS number	EV6475000;
UNII	3G6A5W338E ;
	InChI InChI=1S/C8H10N4O2/c1-10-4-9-6-5(10)7(13)12(3)8(14)11(6)2/h4H,1-3H3 Key: RYYVLZVUVIJVGH-UHFFFAOYSA-N ; InChI=1/C8H10N4O2/c1-10-4-9-6-5(10)7(13)12(3)8(14)11(6)2/h4H,1-3H3 Key: RYYVLZVUVIJVGH-UHFFFAOYAW;
	SMILES O=C2N(c1ncn(c1C(=O)N2C)C)C; Cn1cnc2c1c(=O)n(c(=O)n2C)C;

Caffeine
Hybrid skeletal structure of the caffeine molecule
Names
	IUPAC names 1,3,7-Trimethyl-3,7-dihydro-1H-purine-2,6-dione ; 1,3,7-trimethyl-1H-purine-2,6(3H,7H)-dione; 3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione

This page provides supplementary chemical data on caffeine.

Caffeine
Hazards
GHS labelling:^[4]
Pictograms
Signal word	Warning
Hazard statements	H302
Precautionary statements	P264, P270, P301+P312, P501
NFPA 704 (fire diamond)	2 0 0
Lethal dose or concentration (LD, LC):
LD₅₀ (median dose)	192 mg/kg (rat, oral)^[3]
Safety data sheet (SDS)	ICSC 0405

This box:

^ Caffeine Archived 2011-12-31 at the Wayback Machine, International Occupational Safety and Health Information Centre (CIS)
^ This is the pK_a for protonated caffeine, given as a range of values included in Harry G. Brittain, Richard J. Prankerd (2007). Profiles of Drug Substances, Excipients and Related Methodology, volume 33: Critical Compilation of pK_a Values for Pharmaceutical Substances. Academic Press. ISBN 978-0-12-260833-9.
^ Peters, Josef M. (1967). "Factors Affecting Caffeine Toxicity: A Review of the Literature". The Journal of Clinical Pharmacology and the Journal of New Drugs. 7 (3): 131–141. doi:10.1002/j.1552-4604.1967.tb00034.x. Archived from the original on 2008-06-10. Retrieved 2011-09-25.
^ Merck 102584

Identifiers
CAS Number	58-08-2^Y
3D model (JSmol)	Interactive image Interactive image
Beilstein Reference	17705
ChEBI	CHEBI:27732^Y
ChEMBL	ChEMBL113^Y
ChemSpider	2424^Y
DrugBank	DB00201^Y
EC Number	200-362-1
Gmelin Reference	103040
IUPHAR/BPS	407
KEGG	D00528^Y
PubChem CID	2519
RTECS number	EV6475000
UNII	3G6A5W338E^Y
InChI InChI=1S/C8H10N4O2/c1-10-4-9-6-5(10)7(13)12(3)8(14)11(6)2/h4H,1-3H3^Y Key: RYYVLZVUVIJVGH-UHFFFAOYSA-N^Y InChI=1/C8H10N4O2/c1-10-4-9-6-5(10)7(13)12(3)8(14)11(6)2/h4H,1-3H3 Key: RYYVLZVUVIJVGH-UHFFFAOYAW
SMILES O=C2N(c1ncn(c1C(=O)N2C)C)C Cn1cnc2c1c(=O)n(c(=O)n2C)C

Properties
Chemical formula	C₈H₁₀N₄O₂
Molar mass	194.194 g·mol⁻¹
Appearance	Odorless, white needles or powder
Density	1.23 g/cm³, solid^[1]
Melting point	227 to 228 °C (441 to 442 °F; 500 to 501 K) (anhydrous) 234 to 235 °C (453 to 455 °F; 507 to 508 K) (monohydrate)
Boiling point	178 °C (352 °F; 451 K) (sublimation)
Solubility in water	2.17 g/100 mL (25 °C) 18.0 g/100 mL (80 °C) 67.0 g/100 mL (100 °C)
Acidity (pK_a)	−0.13–1.22^[2]
Dipole moment	3.64 D (calculated)