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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
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

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

Targets

Primary TargetPharmacologyConditionPotency
33.0 µM [IC50]
3.3 µM [Ki]

Conditions

ConditionModalityTargetsHighest PhaseProduct

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
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
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
Record UNII
9O0A545W4L
Record Status Validated (UNII)
Record Version