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Details

Stereochemistry ACHIRAL
Molecular Formula C10H10N2
Molecular Weight 158.1998
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NICOTYRINE

SMILES

CN1C=CC=C1C2=CC=CN=C2

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 158.1998
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
0.17 µM [Ki]
0.37 µM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Studies on the pyrrolinone metabolites derived from the tobacco alkaloid 1-methyl-2-(3-pyridinyl)pyrrole (beta-nicotyrine).
1999 Jun
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

Sample Use Guides

Unknown
Route of Administration: Unknown
Unknown
Substance Class Chemical
Created
by admin
on Fri Dec 15 18:09:02 GMT 2023
Edited
by admin
on Fri Dec 15 18:09:02 GMT 2023
Record UNII
XN4R1LH79Y
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
NICOTYRINE
Common Name English
3-(1-METHYL-1H-PYRROL-2-YL)PYRIDINE
Systematic Name English
NICOTINE RELATED COMPOUND B [USP IMPURITY]
Common Name English
.BETA.-NICOTYRINE
Common Name English
NICOTINE RELATED COMPOUND B [USP-RS]
Common Name English
3,2'-NICOTYRINE
Common Name English
NICOTINE IMPURITY B [EP IMPURITY]
Common Name English
BETA-NICOTYRINE
Common Name English
NSC-407276
Code English
NICOTINE DITARTRATE DIHYDRATE IMPURITY B [EP IMPURITY]
Common Name English
PYRIDINE, 3-(1-METHYL-1H-PYRROL-2-YL)-
Systematic Name English
NICOTINE RESINATE IMPURITY B [EP IMPURITY]
Common Name English
NSC-127943
Code English
Code System Code Type Description
ECHA (EC/EINECS)
207-651-1
Created by admin on Fri Dec 15 18:09:02 GMT 2023 , Edited by admin on Fri Dec 15 18:09:02 GMT 2023
PRIMARY
FDA UNII
XN4R1LH79Y
Created by admin on Fri Dec 15 18:09:02 GMT 2023 , Edited by admin on Fri Dec 15 18:09:02 GMT 2023
PRIMARY
WIKIPEDIA
Nicotyrine
Created by admin on Fri Dec 15 18:09:02 GMT 2023 , Edited by admin on Fri Dec 15 18:09:02 GMT 2023
PRIMARY
NSC
127943
Created by admin on Fri Dec 15 18:09:02 GMT 2023 , Edited by admin on Fri Dec 15 18:09:02 GMT 2023
PRIMARY
PUBCHEM
10249
Created by admin on Fri Dec 15 18:09:02 GMT 2023 , Edited by admin on Fri Dec 15 18:09:02 GMT 2023
PRIMARY
RS_ITEM_NUM
1463337
Created by admin on Fri Dec 15 18:09:02 GMT 2023 , Edited by admin on Fri Dec 15 18:09:02 GMT 2023
PRIMARY
CAS
487-19-4
Created by admin on Fri Dec 15 18:09:02 GMT 2023 , Edited by admin on Fri Dec 15 18:09:02 GMT 2023
PRIMARY
EPA CompTox
DTXSID3075048
Created by admin on Fri Dec 15 18:09:02 GMT 2023 , Edited by admin on Fri Dec 15 18:09:02 GMT 2023
PRIMARY
NSC
407276
Created by admin on Fri Dec 15 18:09:02 GMT 2023 , Edited by admin on Fri Dec 15 18:09:02 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> CONSTITUENT ALWAYS PRESENT
PARENT -> CONSTITUENT ALWAYS PRESENT
METABOLIC ENZYME -> INHIBITOR
Related Record Type Details
PARENT -> IMPURITY
PARENT -> IMPURITY
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP