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Details

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
Structure of HARMINE

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

HIDE SMILES / InChI

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

Description

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

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Diagnostic
Unknown
Primary
Unknown

PubMed

Sample Use Guides

In Vivo Use Guide
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
In Vitro Use Guide
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.
Substance Class Chemical
Record UNII
4FHH5G48T7
Record Status Validated (UNII)
Record Version