Nicotyrine

Nicotryine is lesser known and minor tobacco alkaloid. It inhibits metabolism of nicotine^[2][3] through CYP2A6 enzyme inhibition (K_i = 7.5 ± 2.9).^[2][4][5] It also inhibits CYP2A13 (K_i = 5.6 ± 0.86) which might play role in nicotine metabolism.^[5][6] Nicotyrine is formed by gradual oxidation of nicotine in e-liquids and causes delayed nicotine clearance and attenuated withdrawal symptoms.^[6]

Nicotyrine

Names
IUPAC name 3-(1-methylpyrrol-2-yl)pyridine
Other names alpha-nicotyrine[1] beta-nicotyrine ss-nicotyrine 3,2'-nicotyrine
Identifiers
CAS Number	487-19-4
3D model (JSmol)	Interactive image
ChEBI	CHEBI:7564
ChEMBL	ChEMBL1522291
ChemSpider	2282468
ECHA InfoCard	100.006.956
EC Number	207-651-1
KEGG	C10161
PubChem CID	10249
UNII	XN4R1LH79Y
CompTox Dashboard (EPA)	DTXSID3075048
InChI InChI=1S/C10H10N2/c1-12-7-3-5-10(12)9-4-2-6-11-8-9/h2-8H,1H3 Key: RYFOJXFXERAMLS-UHFFFAOYSA-N
SMILES CN1C=CC=C1C2=CN=CC=C2
Properties
Chemical formula	C10H10N2
Molar mass	158.204 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

It has insecticidal properties like nicotine and certain derivatives have been synthesized for that property.^[7]

Chemistry

alpha-nicotyrine and beta-nicotyrine are positional isomers of each other.

Synthesis

Nicotyrine can be produced readily from nicotine by catalytic dehydrogenation^[8] and from tobacco biomass by catalytic pyrolysis.^[9]

See also

• Myosmine