Nicotryine is lesser known and minor
tobacco alkaloid. It inhibits metabolism of
nicotine
Nicotine is a naturally produced alkaloid in the nightshade family of plants (most predominantly in tobacco and ''Duboisia hopwoodii'') and is widely used recreationally as a stimulant and anxiolytic. As a pharmaceutical drug, it is used fo ...
through
CYP2A6
Cytochrome P450 2A6 (abbreviated CYP2A6) is a member of the cytochrome P450 mixed-function oxidase system, which is involved in the metabolism of xenobiotics in the body. CYP2A6 is the primary enzyme responsible for the oxidation of nicotine and ...
enzyme inhibition (K
i = 7.5 ± 2.9).
It also inhibits
CYP2A13
Cytochrome P450 2A13 is a protein that in humans is encoded by the ''CYP2A13'' gene.
This gene encodes a member of the cytochrome P450 superfamily of enzymes. The cytochrome P450 proteins are monooxygenases which catalyze many reactions involved ...
(K
i = 5.6 ± 0.86) which might play role in nicotine metabolism.
Nicotyrine is formed by gradual oxidation of nicotine in e-liquids and causes delayed nicotine clearance and attenuated
withdrawal symptoms.
It has
insecticidal properties like nicotine and certain derivatives have been synthesized for that property.
Chemistry
alpha-nicotyrine and beta-nicotyrine are
positional isomers of each other.
Synthesis
Nicotyrine can be produced readily from nicotine by catalytic dehydrogenation
and from tobacco biomass by catalytic pyrolysis.
See also
*
Myosmine
References
Pyridine alkaloids
Pyrroles
3-Pyridyl compounds
{{Alkaloid-stub