Description

2-Hydroxynicotine (https://pubchem.ncbi.nlm.nih.gov/compound/2-Hydroxynicotine) is a metabolite of the degradation of Nicotine (https://pubchem.ncbi.nlm.nih.gov/compound/Nicotine) (Nicotine (https://pubchem.ncbi.nlm.nih.gov/compound/Nicotine) is an alkaloid found in the nightshade family of plants (Solanaceae), predominantly in tobacco, and in lower quantities in tomato, potato, eggplant (aubergine), and green pepper) via a 2'-hydroxylation reaction producing 2'-hydroxynicotine (https://pubchem.ncbi.nlm.nih.gov/compound/2%27-hydroxynicotine) as an intermediate in the cytochrome P450 2A6 [EC 1. 14. 14. 1] catalyzed conversion of nicotine (https://pubchem.ncbi.nlm.nih.gov/compound/nicotine) to 4-(methylamino)-1-(3-pyridyl)-1-butanone (https://pubchem.ncbi.nlm.nih.gov/compound/4-%28methylamino%29-1-%283-pyridyl%29-1-butanone). 2'-Hydroxynicotine (https://pubchem.ncbi.nlm.nih.gov/compound/2%27-Hydroxynicotine) spontaneously yields nicotine (https://pubchem.ncbi.nlm.nih.gov/compound/nicotine)-1'(2')-iminium ion, which is in equilibrium with 4-(methylamino)-1-(3-pyridyl)-1-butanone (https://pubchem.ncbi.nlm.nih.gov/compound/4-%28methylamino%29-1-%283-pyridyl%29-1-butanone). About 10% of nicotine (https://pubchem.ncbi.nlm.nih.gov/compound/nicotine) and metabolites is excreted as 4-oxo-4-(3-pyridyl)butanoate (keto acid) and 4-hydroxy-4-(3-pyridyl)butanoate (hydroxy acid) in the urine of smokers.