NICOTYRINE

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 Search

SMILES

CN1C=CC=C1C2=CN=CC=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

Description
Sources: https://www.thevespiary.org/library/Files_Uploaded_by_Users/hex/Nicotine.pdf | https://www.ncbi.nlm.nih.gov/pubmed/22486895 | https://www.ncbi.nlm.nih.gov/pubmed/14757175

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

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Cytochrome P450 2A13 3 Target ID: CHEMBL3542436 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22486895	Inhibitor 8504		0.17 µM [Ki]
Cytochrome P450 2A6 16 Target ID: CHEMBL5282 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22486895 \| https://www.ncbi.nlm.nih.gov/pubmed/14757175	Inhibitor 8504		0.37 µM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2596

PubMed

Title	Date	PubMed
On-Line Chemical Composition Analysis of Refillable Electronic Cigarette Aerosol-Measurement of Nicotine and Nicotyrine.	2015-10	25542921
Electronic cigarettes: The nicotyrine hypothesis.	2015-09	26100465
Nicotine, cotinine, and b-nicotyrine inhibit NNK-induced DNA-strand break in the hepatic cell line HepaRG.	2014-10	25221795
Inhibition and inactivation of cytochrome P450 2A6 and cytochrome P450 2A13 by menthofuran, β-nicotyrine and menthol.	2012-05-30	22486895
Nicotine-related alkaloids and metabolites as inhibitors of human cytochrome P-450 2A6.	2004-02-15	14757175
Studies on the in vivo biotransformation of the tobacco alkaloid beta-nicotyrine.	2000-05	10813649
Studies on the pyrrolinone metabolites derived from the tobacco alkaloid 1-methyl-2-(3-pyridinyl)pyrrole (beta-nicotyrine).	1999-06	10368313
Liver and lung microsomal metabolism of the tobacco alkaloid beta-nicotyrine.	1989-09-01	2519819
Nicotyrine inhibits in vivo metabolism of nicotine without increasing its toxicity.	1982-09-30	7157369

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Mon Mar 31 19:04:55 GMT 2025` Edited by `admin` on `Mon Mar 31 19:04:55 GMT 2025`
Record UNII	XN4R1LH79Y
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NICOTYRINE

Common Name

English

NSC-127943

Preferred 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

Code System Code Type Description

ECHA (EC/EINECS)

207-651-1