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Details

Stereochemistry ACHIRAL
Molecular Formula C10H10N2
Molecular Weight 158.2002
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NICOTYRINE

SMILES

Cn1cccc1-c2cccnc2

InChI

InChIKey=RYFOJXFXERAMLS-UHFFFAOYSA-N
InChI=1S/C10H10N2/c1-12-7-3-5-10(12)9-4-2-6-11-8-9/h2-8H,1H3

HIDE SMILES / InChI

Molecular Formula C10H10N2
Molecular Weight 158.2002
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

1-methyl-4-(3-pyridinyl) pyrrole (β-nicotyrine) is a tobacco alkaloid. It is a potent inhibitor of cytochrome P450 CYP2A13 and a mechanism-based inactivator of cytochrome P450 CYP2A6.

Originator

Sources: Cahours and Etard, Bulletin Societe Chimique, vol. 34, page 449 (1880)
Curator's Comment:: reference retrieved from https://www.thevespiary.org/library/Files_Uploaded_by_Users/hex/Nicotine.pdf | https://books.google.ru/books?id=g_jJCgAAQBAJ&printsec=frontcover&hl=ru#v=onepage&q&f=false

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
0.170000000000000012 µM [Ki]
0.369999999999999996 µM [Ki]
PubMed

PubMed

TitleDatePubMed
Nicotyrine inhibits in vivo metabolism of nicotine without increasing its toxicity.
1982 Sep 30
Liver and lung microsomal metabolism of the tobacco alkaloid beta-nicotyrine.
1989 Sep-Oct
Studies on the pyrrolinone metabolites derived from the tobacco alkaloid 1-methyl-2-(3-pyridinyl)pyrrole (beta-nicotyrine).
1999 Jun
Studies on the in vivo biotransformation of the tobacco alkaloid beta-nicotyrine.
2000 May
Nicotine-related alkaloids and metabolites as inhibitors of human cytochrome P-450 2A6.
2004 Feb 15
Inhibition and inactivation of cytochrome P450 2A6 and cytochrome P450 2A13 by menthofuran, β-nicotyrine and menthol.
2012 May 30
Nicotine, cotinine, and b-nicotyrine inhibit NNK-induced DNA-strand break in the hepatic cell line HepaRG.
2014 Oct
On-Line Chemical Composition Analysis of Refillable Electronic Cigarette Aerosol-Measurement of Nicotine and Nicotyrine.
2015 Oct
Electronic cigarettes: The nicotyrine hypothesis.
2015 Sep
Patents
Substance Class Chemical
Created
by admin
on Sat Jun 26 03:43:15 UTC 2021
Edited
by admin
on Sat Jun 26 03:43:15 UTC 2021
Record UNII
XN4R1LH79Y
Record Status Validated (UNII)
Record Version
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Name Type Language
NICOTYRINE
Common Name English
3-(1-METHYL-1H-PYRROL-2-YL)PYRIDINE
Systematic Name English
.BETA.-NICOTYRINE
Common Name English
NICOTINE RELATED COMPOUND B [USP-RS]
Common Name English
3,2'-NICOTYRINE
Common Name English
BETA-NICOTYRINE
Common Name English
NICOTINE DITARTRATE DIHYDRATE SPECIFIED IMPURITY B [EP]
Common Name English
NSC-407276
Code English
PYRIDINE, 3-(1-METHYL-1H-PYRROL-2-YL)-
Systematic Name English
NICOTINE RELATED COMPOUND B
USP-RS  
Common Name English
NICOTINE SPECIFIED IMPURITY B [EP]
Common Name English
NICOTINE RESINATE SPECIFIED IMPURITY B [EP]
Common Name English
NSC-127943
Code English
Code System Code Type Description
ECHA (EC/EINECS)
207-651-1
Created by admin on Sat Jun 26 03:43:16 UTC 2021 , Edited by admin on Sat Jun 26 03:43:16 UTC 2021
PRIMARY
FDA UNII
XN4R1LH79Y
Created by admin on Sat Jun 26 03:43:16 UTC 2021 , Edited by admin on Sat Jun 26 03:43:16 UTC 2021
PRIMARY
PUBCHEM
10249
Created by admin on Sat Jun 26 03:43:16 UTC 2021 , Edited by admin on Sat Jun 26 03:43:16 UTC 2021
PRIMARY
USP_CATALOG
1463337
Created by admin on Sat Jun 26 03:43:16 UTC 2021 , Edited by admin on Sat Jun 26 03:43:16 UTC 2021
PRIMARY USP-RS
CAS
487-19-4
Created by admin on Sat Jun 26 03:43:16 UTC 2021 , Edited by admin on Sat Jun 26 03:43:16 UTC 2021
PRIMARY
EPA CompTox
487-19-4
Created by admin on Sat Jun 26 03:43:16 UTC 2021 , Edited by admin on Sat Jun 26 03:43:16 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> CONSTITUENT ALWAYS PRESENT
PARENT -> CONSTITUENT ALWAYS PRESENT
METABOLIC ENZYME -> INHIBITOR
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PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP