9H-xanthine 2026-11-05
9H-xanthine is a neutral tautomer of xanthine in which the indicated hydrogen is attached to nitrogen9 of the purine framework. The oxo groups remain at positions2 and6. ChEBI identifies this particular form as CHEBI:17712, distinct from the broader tautomer-unspecified xanthine entry.[ref]
Its molecular formula is . The prefix 9H is an atom-location convention, not a count of nine hydrogens: the entire neutral molecule contains four hydrogens. As a simple inventory check, it contains atoms in all.
7H-xanthine has the same elemental formula and net charge but a different indicated hydrogen position. A mass measurement consistent with that formula therefore does not alone assign the 9H form. The distinction concerns tautomerism, rather than the gain of an extra proton or a change in carbon/oxygen composition.[ref]
Xanthine in ChEBI. CHEBI:17712 and CHEBI:48517, neutral charge and reciprocal tautomer relation
Tautomer 2026-11-05
A tautomer is one of the readily interconvertible constitutional isomers related by tautomerism. In a proton-transfer example, the forms retain the same atom inventory and net charge but differ in where a hydrogen is attached and in associated bond orders. A molecular formula alone therefore cannot identify which tautomer is meant.[ref]
IUPAC Compendium of Chemical Terminology, fifth edition (Gold Book) by International Union of Pure and Applied Chemistry. Entry T06252: tautomers and the prototropic case
Xanthine supplies a concrete example. ChEBI distinguishes 7H-xanthine, with the indicated hydrogen on nitrogen7, from 9H-xanthine, with it on nitrogen9. Both neutral forms have formula , and the curated records explicitly identify them as tautomers. The atom inventory is identical while the indicated hydrogen placement differs.[ref]