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
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
| 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.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL5282 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14757175 |
|||
Target ID: CHEMBL1978 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19601869 |
33.0 µM [IC50] | ||
Target ID: WP408 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22450200 |
|||
Target ID: CHEMBL3301382 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12639569 |
3.3 µM [Ki] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
PubMed
| Title | Date | PubMed |
|---|---|---|
| Piperidine, pyridine alkaloid inhibition of fetal movement in a day 40 pregnant goat model. | 2013-08 |
|
| Formation and repair of tobacco carcinogen-derived bulky DNA adducts. | 2010-12-20 |
|
| A novel pathway for nicotine degradation by Aspergillus oryzae 112822 isolated from tobacco leaves. | 2010-09 |
|
| The pyrolysis of (-)-(S)-nicotine: racemization and decomposition. | 2010-05-05 |
|
| Electronic cigarettes: a survey of users. | 2010-05-04 |
|
| The addition of five minor tobacco alkaloids increases nicotine-induced hyperactivity, sensitization and intravenous self-administration in rats. | 2009-11 |
|
| Analysis of myosmine, cotinine and nicotine in human toenail, plasma and saliva. | 2009-08 |
|
| 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. | 2009-07-12 |
|
| Inhibition of human aromatase by myosmine. | 2009-04 |
|
| Evaluation of the mutagenic effects of myosmine in human lymphocytes using the HPRT gene mutation assay. | 2009-01 |
|
| Enhanced radiation damage in irradiated and non-irradiated bystander regions by co-exposure to myosmine. | 2009-01 |
|
| [Rapid determination of alkaloids in tobacco using gas chromatography-mass spectrometry with full scan-selected ion monitoring mode]. | 2008-05 |
|
| Sequential preconcentration by coupling of field amplified sample injection with pseudo isotachophoresis-acid stacking for analysis of alkaloids in capillary electrophoresis. | 2008-03 |
|
| Analyses of tobacco alkaloids by cation-selective exhaustive injection sweeping microemulsion electrokinetic chromatography. | 2007-09-14 |
|
| Investigation of the reaction of myosmine with sodium nitrite in vitro and in rats. | 2007-03 |
|
| Tissue distribution and excretion of myosmine after i.v. administration to Long-Evans rats using quantitative whole-body autoradiography. | 2007-03 |
|
| 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 |
|
| The tobacco industry's role in the 16 Cities Study of secondhand tobacco smoke: do the data support the stated conclusions? | 2006-12 |
|
| Genotoxic effects of myosmine in a human esophageal adenocarcinoma cell line. | 2006-05-01 |
|
| Reaction of the tobacco alkaloid myosmine with hydrogen peroxide. | 2006-01 |
|
| Acute and subacute effects of tobacco alkaloids, tobacco-specific nitrosamines and phenethyl isothiocyanate on N'-nitrosonornicotine metabolism in rats. | 2005-11-15 |
|
| Metabolism of myosmine in Wistar rats. | 2005-11 |
|
| Nicotine demethylation in Nicotiana cell suspension cultures: N'-formylnornicotine is not involved. | 2005-10 |
|
| Iminium metabolite mechanism for nicotine toxicity and addiction: Oxidative stress and electron transfer. | 2005 |
|
| Nicotine-related alkaloids and metabolites as inhibitors of human cytochrome P-450 2A6. | 2004-02-15 |
|
| Toxicological assessment of noxious inhalants. | 2004 |
|
| Genotoxic effects of myosmine in human lymphocytes and upper aerodigestive tract epithelial cells. | 2003-11-05 |
|
| Fast analysis of nicotine related alkaloids in tobacco and cigarette smoke by megabore capillary gas chromatography. | 2003-10-31 |
|
| New sources of dietary myosmine uptake from cereals, fruits, vegetables, and milk. | 2002-08-14 |
|
| Nitrosation of dietary myosmine as risk factor of human cancer. | 2002-08 |
|
| Determination of tobacco alkaloids by gas chromatography with nitrogen-phosphorus detection. | 2002-04 |
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/14580784
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
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| Record UNII |
9O0A545W4L
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Validated (UNII)
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C002398
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Myosmine
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| Related Record | Type | Details | ||
|---|---|---|---|---|
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PARENT -> CONSTITUENT ALWAYS PRESENT |
The other minor alkaloids (myosmine, anabasine,
and anatabine) have the same (leaf) distribution pattern
as nicotine (figures not presented).
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| Related Record | Type | Details | ||
|---|---|---|---|---|
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PARENT -> IMPURITY | |||
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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PARENT -> IMPURITY |