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 |
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Target ID: CHEMBL5282 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14757175 |
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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 |
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Target ID: CHEMBL3301382 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12639569 |
3.3 µM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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PubMed
Title | Date | PubMed |
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Nitrosation of dietary myosmine as risk factor of human cancer. | 2002 Aug |
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New sources of dietary myosmine uptake from cereals, fruits, vegetables, and milk. | 2002 Aug 14 |
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Toxicological assessment of noxious inhalants. | 2004 |
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Nicotine-related alkaloids and metabolites as inhibitors of human cytochrome P-450 2A6. | 2004 Feb 15 |
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Iminium metabolite mechanism for nicotine toxicity and addiction: Oxidative stress and electron transfer. | 2005 |
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The tobacco industry's role in the 16 Cities Study of secondhand tobacco smoke: do the data support the stated conclusions? | 2006 Dec |
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Genotoxic effects of myosmine in a human esophageal adenocarcinoma cell line. | 2006 May 1 |
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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 |
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Investigation of the reaction of myosmine with sodium nitrite in vitro and in rats. | 2007 Mar |
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Inhibition of human aromatase by myosmine. | 2009 Apr |
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Evaluation of the mutagenic effects of myosmine in human lymphocytes using the HPRT gene mutation assay. | 2009 Jan |
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Enhanced radiation damage in irradiated and non-irradiated bystander regions by co-exposure to myosmine. | 2009 Jan |
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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 |
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Formation and repair of tobacco carcinogen-derived bulky DNA adducts. | 2010 Dec 20 |
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Electronic cigarettes: a survey of users. | 2010 May 4 |
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The pyrolysis of (-)-(S)-nicotine: racemization and decomposition. | 2010 May 5 |
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A novel pathway for nicotine degradation by Aspergillus oryzae 112822 isolated from tobacco leaves. | 2010 Sep |
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Piperidine, pyridine alkaloid inhibition of fetal movement in a day 40 pregnant goat model. | 2013 Aug |
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
by
admin
on
Edited
Thu Jul 06 01:06:05 UTC 2023
by
admin
on
Thu Jul 06 01:06:05 UTC 2023
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Record UNII |
9O0A545W4L
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Record Status |
Validated (UNII)
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Record Version |
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9O0A545W4L
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C002398
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Myosmine
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442649
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DTXSID70891866
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532-12-7
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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 |