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=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

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 8297		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 8297		0.37 µM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2578

PubMed

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

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 `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

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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