Caffeine
C₈H₁₀N₄O₂·194.191 g/mol·Pharmaceutical·CID 2519
StimulantCommon
The world's most widely consumed psychoactive substance. A purine alkaloid that blocks adenosine receptors, promoting wakefulness. Found in coffee (~95 mg/cup), tea (~45 mg/cup), and chocolate. Half-life ~5 hours in humans.
IUPAC: 1,3,7-trimethylpurine-2,6-dione
Also known as: 58-08-2, Guaranine, 1,3,7-Trimethylxanthine, Methyltheobromine, Theine (+14 more)
Molecular Structure
Molecular Propertiesmass · H-bonds · stereo
Molecular Weight
194.190g/mol
Exact Mass
194.080376Da
Monoisotopic Mass
194.080376Da
XLogP
-0.1
Polar Surface Area
58.4Ų
Complexity
293
Formal Charge
0
H-Bond Donors
0
H-Bond Acceptors
3
Rotatable Bonds
0
Heavy Atoms
14
Stereo Centers
0
Bond Stereo
0
Drug-Likeness (Lipinski's Rule of Five)
✓ 194.2 g/mol
MW ≤ 500
✓ -0.1
LogP ≤ 5
✓ 0
H-bond donors ≤ 5
✓ 3
H-bond acceptors ≤ 10
Passes all rules — good oral bioavailability predicted
GHS Hazard Classification
Danger
Hazards
H302Harmful if swallowedH301Toxic if swallowedH332Harmful if inhaledH360May damage fertility or the unborn child
Source: PubChem GHS Classification. Always consult the SDS for handling.
Chemical IdentifiersSMILES · InChI
InChI
InChI=1S/C8H10N4O2/c1-10-4-9-6-5(10)7(13)12(3)8(14)11(6)2/h4H,1-3H3
Constituent Elements
Isomers8 compounds with formula C₈H₁₀N₄O₂
3-propyl-7H-purine-2,6-dione
CID 1676 · 194.2 g/mol
benzene-1,3-dicarbohydrazide
CID 72700 · 194.2 g/mol
N-methyl-N-[(4-nitrophenyl)diazenyl]methanamine
CID 81648 · 194.2 g/mol
1,3,9-trimethylpurine-2,6-dione
CID 1326 · 194.2 g/mol
2,4-dicyano-3-methylpentanediamide
CID 95498 · 194.2 g/mol
1,3,8-trimethyl-7H-purine-2,6-dione
CID 95030 · 194.2 g/mol
N-methyl-N-[(3-nitrophenyl)diazenyl]methanamine
CID 88426 · 194.2 g/mol
benzene-1,4-dicarbohydrazide
CID 67294 · 194.2 g/mol