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 |
---|---|---|
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 |
|
Fast analysis of nicotine related alkaloids in tobacco and cigarette smoke by megabore capillary gas chromatography. | 2003 Oct 31 |
|
Toxicological assessment of noxious inhalants. | 2004 |
|
Iminium metabolite mechanism for nicotine toxicity and addiction: Oxidative stress and electron transfer. | 2005 |
|
Acute and subacute effects of tobacco alkaloids, tobacco-specific nitrosamines and phenethyl isothiocyanate on N'-nitrosonornicotine metabolism in rats. | 2005 Nov 15 |
|
[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 |
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
Mon Mar 31 18:53:26 GMT 2025
by
admin
on
Mon Mar 31 18:53:26 GMT 2025
|
Record UNII |
9O0A545W4L
|
Record Status |
Validated (UNII)
|
Record Version |
|
-
Download
Name | Type | Language | ||
---|---|---|---|---|
|
Common Name | English | ||
|
Preferred Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English |
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
9O0A545W4L
Created by
admin on Mon Mar 31 18:53:26 GMT 2025 , Edited by admin on Mon Mar 31 18:53:26 GMT 2025
|
PRIMARY | |||
|
C002398
Created by
admin on Mon Mar 31 18:53:26 GMT 2025 , Edited by admin on Mon Mar 31 18:53:26 GMT 2025
|
PRIMARY | |||
|
Myosmine
Created by
admin on Mon Mar 31 18:53:26 GMT 2025 , Edited by admin on Mon Mar 31 18:53:26 GMT 2025
|
PRIMARY | |||
|
442649
Created by
admin on Mon Mar 31 18:53:26 GMT 2025 , Edited by admin on Mon Mar 31 18:53:26 GMT 2025
|
PRIMARY | |||
|
DTXSID70891866
Created by
admin on Mon Mar 31 18:53:26 GMT 2025 , Edited by admin on Mon Mar 31 18:53:26 GMT 2025
|
PRIMARY | |||
|
532-12-7
Created by
admin on Mon Mar 31 18:53:26 GMT 2025 , Edited by admin on Mon Mar 31 18:53:26 GMT 2025
|
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 |