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Details

Stereochemistry ACHIRAL
Molecular Formula C9H10N2
Molecular Weight 146.1891
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MYOSMINE

SMILES

C1CN=C(C1)C2=CN=CC=C2

InChI

InChIKey=DPNGWXJMIILTBS-UHFFFAOYSA-N
InChI=1S/C9H10N2/c1-3-8(7-10-5-1)9-4-2-6-11-9/h1,3,5,7H,2,4,6H2

HIDE SMILES / InChI

Molecular Formula C9H10N2
Molecular Weight 146.1891
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Myosmine (3-(1-pyrrolin-2-yl)pyridine) is a minor tobacco alkaloid widely occurring in food products of plant and animal origin. Myosmine expresses significant genotoxic effects in human target cells of carcinogenesis. After nitrosation and/or peroxidation, myosmine gives rise to reactive pyridyloxobutylating species which are capable of forming pyridyloxobutylated DNA adducts.

CNS Activity

Approval Year

PubMed

PubMed

TitleDatePubMed
Determination of tobacco alkaloids by gas chromatography with nitrogen-phosphorus detection.
2002 Apr
Nitrosation of dietary myosmine as risk factor of human cancer.
2002 Aug
New sources of dietary myosmine uptake from cereals, fruits, vegetables, and milk.
2002 Aug 14
Genotoxic effects of myosmine in human lymphocytes and upper aerodigestive tract epithelial cells.
2003 Nov 5
Toxicological assessment of noxious inhalants.
2004
Acute and subacute effects of tobacco alkaloids, tobacco-specific nitrosamines and phenethyl isothiocyanate on N'-nitrosonornicotine metabolism in rats.
2005 Nov 15
Nicotine demethylation in Nicotiana cell suspension cultures: N'-formylnornicotine is not involved.
2005 Oct
The tobacco industry's role in the 16 Cities Study of secondhand tobacco smoke: do the data support the stated conclusions?
2006 Dec
Reaction of the tobacco alkaloid myosmine with hydrogen peroxide.
2006 Jan
Genotoxic effects of myosmine in a human esophageal adenocarcinoma cell line.
2006 May 1
Characterisation of nicotine and related compounds using electrospray ionisation with ion trap mass spectrometry and with quadrupole time-of-flight mass spectrometry and their detection by liquid chromatography/electrospray ionisation mass spectrometry.
2007
Investigation of the reaction of myosmine with sodium nitrite in vitro and in rats.
2007 Mar
Tissue distribution and excretion of myosmine after i.v. administration to Long-Evans rats using quantitative whole-body autoradiography.
2007 Mar
[Rapid determination of alkaloids in tobacco using gas chromatography-mass spectrometry with full scan-selected ion monitoring mode].
2008 May
Inhibition of human aromatase by myosmine.
2009 Apr
Analysis of myosmine, cotinine and nicotine in human toenail, plasma and saliva.
2009 Aug
Validation of a GC-FID method for rapid quantification of nicotine in fermented extracts prepared from Nicotiana tabacum fresh leaves and studies of nicotine metabolites.
2009 Jul 12
The addition of five minor tobacco alkaloids increases nicotine-induced hyperactivity, sensitization and intravenous self-administration in rats.
2009 Nov
Formation and repair of tobacco carcinogen-derived bulky DNA adducts.
2010 Dec 20
Electronic cigarettes: a survey of users.
2010 May 4
The pyrolysis of (-)-(S)-nicotine: racemization and decomposition.
2010 May 5
A novel pathway for nicotine degradation by Aspergillus oryzae 112822 isolated from tobacco leaves.
2010 Sep
Piperidine, pyridine alkaloid inhibition of fetal movement in a day 40 pregnant goat model.
2013 Aug
Patents

Patents

Sample Use Guides

Myosmine (10-50mg/kg) produced time- and dose-dependent patterns of effects on locomotor activity in rats. Wistar rats received a single i.p. injection of 19 mg/ kg of myosmine and an oral dose of 190 mg/kg by gavage.
Route of Administration: Other
Possible genotoxic effects of myosmine were studied in human lymphocytes and nasal mucosal cells using the alkaline single cell microgel electrophoresis (Comet) assay. DNA single strand breaks, alkali labile sites and incomplete excision repair sites were expressed using the Olive tail moment (OTM). One hour incubation with myosmine at 0, 5, 10, 25 and 50 mM induced a low but significantly dose-dependent increase of DNA migration from 1.29 +/- 0.13 to 18.25 +/- 1.59 (OTM, mean +/- S.E., N=11) in lymphocytes. In nasal mucosal cells a similar although somewhat less extensive DNA damage from 1.17 +/- 0.12 to 21.67 +/- 2.97 (OTM, mean +/- S.E., N=10-11) was obtained after 1 h incubation with myosmine at 0, 10, 25, 50 and 100 mM. After prolonged incubation of human lymphocytes with 10mM myosmine for 1, 3, 6, and 24 h, a significant time-dependent increase of DNA migration from 3.45 +/- 0.43 to 57.77 +/- 8.24 (OTM, mean +/- S.E., N=4) was observed. Our data indicate that myosmine expresses significant genotoxic effects in human target cells of carcinogenesis
Substance Class Chemical
Created
by admin
on Fri Dec 15 17:48:43 GMT 2023
Edited
by admin
on Fri Dec 15 17:48:43 GMT 2023
Record UNII
9O0A545W4L
Record Status Validated (UNII)
Record Version
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Name Type Language
MYOSMINE
Common Name English
3-(4,5-DIHYDRO-3H-PYRROL-2-YL)PYRIDINE
Systematic Name English
NICOTINE DITARTRATE DIHYDRATE IMPURITY D [EP IMPURITY]
Common Name English
NICOTINE RESINATE IMPURITY D [EP IMPURITY]
Common Name English
2-(3-PYRIDYL)-1-PYRROLINE
Systematic Name English
NICOTINE RELATED COMPOUND D [USP IMPURITY]
Common Name English
NICOTINE IMPURITY D [EP IMPURITY]
Common Name English
PYRIDINE, 3-(3,4-DIHYDRO-2H-PYRROL-5-YL)-
Systematic Name English
Code System Code Type Description
FDA UNII
9O0A545W4L
Created by admin on Fri Dec 15 17:48:43 GMT 2023 , Edited by admin on Fri Dec 15 17:48:43 GMT 2023
PRIMARY
MESH
C002398
Created by admin on Fri Dec 15 17:48:43 GMT 2023 , Edited by admin on Fri Dec 15 17:48:43 GMT 2023
PRIMARY
WIKIPEDIA
Myosmine
Created by admin on Fri Dec 15 17:48:43 GMT 2023 , Edited by admin on Fri Dec 15 17:48:43 GMT 2023
PRIMARY
PUBCHEM
442649
Created by admin on Fri Dec 15 17:48:43 GMT 2023 , Edited by admin on Fri Dec 15 17:48:43 GMT 2023
PRIMARY
EPA CompTox
DTXSID70891866
Created by admin on Fri Dec 15 17:48:43 GMT 2023 , Edited by admin on Fri Dec 15 17:48:43 GMT 2023
PRIMARY
CAS
532-12-7
Created by admin on Fri Dec 15 17:48:43 GMT 2023 , Edited by admin on Fri Dec 15 17:48:43 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> CONSTITUENT ALWAYS PRESENT
The other minor alkaloids (myosmine, anabasine, and anatabine) have the same (leaf) distribution pattern as nicotine (figures not presented).
Related Record Type Details
PARENT -> IMPURITY
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
PARENT -> IMPURITY