Stereochemistry | ACHIRAL |
Molecular Formula | C13H12N2O |
Molecular Weight | 212.2472 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
COC1=CC2=C(C=C1)C3=C(N2)C(C)=NC=C3
InChI
InChIKey=BXNJHAXVSOCGBA-UHFFFAOYSA-N
InChI=1S/C13H12N2O/c1-8-13-11(5-6-14-8)10-4-3-9(16-2)7-12(10)15-13/h3-7,15H,1-2H3
Molecular Formula | C13H12N2O |
Molecular Weight | 212.2472 |
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 |
Harmine (aka telepathine) is a fluorescent harmala alkaloid belonging to the beta-carboline family of compounds. It is a naturally occurring metabolite in a number of plants, notably the Middle Eastern plant harmal or Syrian rue (Peganum harmala) and the South American vine Banisteriopsis caapi. Harmine is a reversible inhibitor of monoamine oxidase A (MAO-A), but not MAO-B. Harmine has been found to have potential anti-cancer and neuroprotective properties, and also promotes differentiation of osteoblasts and chondrocytes while inhibiting osteoclastogenesis. Harmine has also been used as a C-11 labeled probe in positron emission tomography.
CNS Activity
Approval Year
Sample Use Guides
Five healthy male volunteers free of neurologic or psychiatric diseases, with no past or current history of cigarette smoking, were intravenously injected with a saline solution of 10.9 mCi (s.d. ¼ 1.0 mCi) of [11C]-harmine at a specific radioactivity of 1,124 Ci/mmol (s.d. ¼ 203 Ci/mmol) as a bolus and immediately flushed with 10 mL saline. Radioactivity in the brain was measured by Positron Emission Tomography PET in a series of sequential frames of increasing duration (from 1 to 5 mins).
Route of Administration:
Intravenous
Human HepG2 cells were cultured in RPMI-1640 medium supplemented with 10% fetal bovine serum at 37 deg-C in a 5% CO2 atmosphere. Harmine was dissolved in dimethyl sulfoxide and diluted to appropriate concentrations with culture medium. The CCK-8 test was used to monitor cell proliferation. Cells were plated at a density of 5000 cells per well in 96 well plates. After 24 hours, the cultures were treated with harmine at concentrations of 0, 0.625, 1.25, 2.5, 5, 10, or 20 μg/mL for 48 hours. After addition of test compounds, 10 μL CCK-8 was added to each well. Harmine inhibited the growth of HepG2 cells in a dose-dependent manner, with an IC50 of 9.80 μg/mL.