<img src="https://pubchem.ncbi.nlm.nih.gov/image/imgsrv.fcgi?cid=64969&t=l" alt="3-Methylhistidine" /> 3-Methylhistidine, also known as 3-MHis, 3MH, pi-methylhistidine or pros-methylhistidine, belongs to the class of organic compounds known as histidine and derivatives. 3MH is also classified as a methylamino acid. Methylamino acids are primarily proteogenic amino acids (found in proteins) which have been methylated (in situ) on their side chains by various methyltransferase enzymes. Histidine can be methylated at either the N1 or N3 position of its imidazole ring, yielding the isomers 1-methylhistidine (1MH; also referred to as tau-methylhistidine, according to IUPAC) or 3-methylhistidine (3MH; pi-methylhistidine, according to IUPAC), respectively. There is considerable confusion with regard to the nomenclature of the methylated nitrogen atoms on the imidazole ring of histidine in histidine-containing proteins (such as actin and myosin) as well as histidine-containing peptides (such as anserine and ophidine/balenine). In particular, older literature (mostly prior to the year 2000) as well as most biochemists and nutrition scientists incorrectly number the imidazole nitrogen atom most proximal to the side chain beta-carbon as 1 or N1, while organic chemists correctly designate it as 3 or N3. As a result, biochemists and nutrition scientists historically designated anserine (Npi-methylated) as beta-alanyl-N1-methylhistidine (or beta-alanyl-1-methylhistidine), whereas according to standard IUPAC nomenclature, anserine is correctly named as beta-alanyl-N3-methylhistidine. As a result, for several decades, many papers incorrectly identified 1MH as a specific marker for dietary consumption or various pathophysiological effects when they really are referring to 3MH – and vice versa

Property Value
Metabolite name 3-Methylhistidine
PubChem CID 64969
ChEBI ID 27596
Molecular formula C7H11N3O2
Molecular weight 169.1811
Monoisotopic mass 169.085126611
IUPAC name (2S)-2-amino-3-(1-methyl-1H-imidazol-5-yl)propanoic acid


3-Methylhistidine, 3-Methyl-L-histidine, pi-methylhistidine, pros-methylhistidine, pi methylhistidine, pros methylhistidine, Nπ-methyl-L-histidine, N(pai)-Methyl-L-histidine, π-Methylhistidine

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