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
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 |
---|---|---|
Toxicological assessment of noxious inhalants. | 2004 |
|
Nicotine-related alkaloids and metabolites as inhibitors of human cytochrome P-450 2A6. | 2004 Feb 15 |
|
Metabolism of myosmine in Wistar rats. | 2005 Nov |
|
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 |
|
Tissue distribution and excretion of myosmine after i.v. administration to Long-Evans rats using quantitative whole-body autoradiography. | 2007 Mar |
|
Evaluation of the mutagenic effects of myosmine in human lymphocytes using the HPRT gene mutation assay. | 2009 Jan |
|
Enhanced radiation damage in irradiated and non-irradiated bystander regions by co-exposure to myosmine. | 2009 Jan |
|
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
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
Name | Type | Language | ||
---|---|---|---|---|
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English |
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 |
SUBSTANCE RECORD