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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
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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: O95644|||Q12865
Gene ID: 4772.0
Gene Symbol: NFATC1
Target Organism: Homo sapiens (Human)
Target ID: Q02363
Gene ID: 3398.0
Gene Symbol: ID2
Target Organism: Homo sapiens (Human)
Target ID: P21397
Gene ID: 4128.0
Gene Symbol: MAOA
Target Organism: Homo sapiens (Human)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Diagnostic
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Antitumor and neurotoxic effects of novel harmine derivatives and structure-activity relationship analysis.
2005-05-01
Encapsulation of norharmane in cyclodextrin: formation of 1:1 and 1:2 inclusion complexes.
2005-03-01
Lack of combination hepatocarcinogenicity of harman, norharman and amitrole when given with NaNO2 in the rat.
2005-02
Modulation of voltage-gated channel currents by harmaline and harmane.
2005-01
Matrix-assisted ultraviolet laser desorption/ionization time-of-flight mass spectrometry of beta-(1 --> 3), beta-(1 --> 4)-xylans from Nothogenia fastigiata using nor-harmane as matrix.
2005
Harmane and harmalan are bioactive components of classical clonidine-displacing substance.
2004-12-28
Photophysics in motionally constrained bioenvironment: interaction of norharmane with bovine serum albumin.
2004-12-14
Relative exposure to beta-carbolines norharman and harman from foods and tobacco smoke.
2004-11
The putative imidazoline receptor agonist, harmane, promotes intracellular calcium mobilisation in pancreatic beta-cells.
2004-10-06
Protective effect of 1-methylated beta-carbolines against 3-morpholinosydnonimine-induced mitochondrial damage and cell viability loss in PC12 cells.
2004-10
Tacrolimus-induced neurotoxicity and nephrotoxicity is ameliorated by administration in the dark phase in rats.
2004-10
Norharman and alcohol-dependency in male Wistar rats.
2004-10
Carcinogenicity of aminophenylnorharman, a possible novel endogenous mutagen, formed from norharman and aniline, in F344 rats.
2004-10
Synthesis, acute toxicities, and antitumor effects of novel 9-substituted beta-carboline derivatives.
2004-09-01
Identification of cytochrome P-450s involved in the formation of APNH from norharman with aniline.
2004-08-08
Antibiotic-mediated release of tumour necrosis factor alpha and norharman in patients with hospital-acquired pneumonia and septic encephalopathy.
2004-08
Modulation of cytochrome P450 1A1 by food-derived heterocyclic aromatic amines.
2004-07-01
Ultrastructural changes induced in HeLa cells after phototoxic treatment with harmine.
2004-06-24
Photophysics of norharmane in micellar environments: a fluorometric study.
2004-05-01
Dopamine transporter-mediated cytotoxicity of beta-carbolinium derivatives related to Parkinson's disease: relationship to transporter-dependent uptake.
2004-05
Specific inhibition of cyclin-dependent kinases and cell proliferation by harmine.
2004-04-23
Harmine: evaluation of its antileishmanial properties in various vesicular delivery systems.
2004-04
Transport of harman alkaloids across Caco-2 cell monolayers.
2004-04
Effects of ayahuasca on binocular rivalry with dichoptic stimulus alternation.
2004-04
Exposure to beta-carbolines norharman and harman.
2004-03-25
Trypanocidal constituents in plants 3. Leaves of Garcinia intermedia and heartwood of Calophyllum brasiliense.
2004-01
Effects of the beta-carbolines, harmane and pinoline, on insulin secretion from isolated human islets of Langerhans.
2003-12-15
Atypical [(3)H]clonidine binding sites in human caudate and platelets on cryostat-cut sections.
2003-12
Endogenous imidazoline receptor ligands relax rat aorta by an endothelium-dependent mechanism.
2003-12
Harmane induces anxiolysis and antidepressant-like effects in rats.
2003-12
Effect of harmane on the convulsive threshold in epilepsy models in mice.
2003-12
Inhibitory effect of harmane on morphine-dependent Guinea pig ileum.
2003-12
Effect of harmane on mononeuropathic pain in rats.
2003-12
Characterization of [(3)H]harmane binding to rat whole brain membranes.
2003-12
Endogenous beta-carbolines as clonidine-displacing substances.
2003-12
Craving for cigarettes among low and high dependent smokers: impact of norharman.
2003-12
Potent genotoxicity of aminophenylnorharman, formed from non-mutagenic norharman and aniline, in the liver of gpt delta transgenic mouse.
2003-12
Effects of the Amazonian psychoactive beverage Ayahuasca on binocular rivalry: interhemispheric switching or interhemispheric fusion?
2003-11-19
Possibility of the involvement of 9H-pyrido[3,4-b]indole (norharman) in carcinogenesis via inhibition of cytochrome P450-related activities and intercalation to DNA.
2003-11-10
Effects of harman and harmine on naloxone-precipitated withdrawal syndrome in morphine-dependent rats.
2003-09-19
Detection and characterization of cyclodextrin complexes with beta-carboline derivatives by spectroscopic techniques.
2003-08-08
Demonstration of high monoaminoxidase-A levels in neuroendocrine gastroenteropancreatic tumors in vitro and in vivo-tumor visualization using positron emission tomography with 11C-harmine.
2003-08
Human pharmacology of ayahuasca: subjective and cardiovascular effects, monoamine metabolite excretion, and pharmacokinetics.
2003-07
Activities of extract and constituents of Banisteriopsis caapi relevant to parkinsonism.
2003-06
Agmatine and imidazoline systems--fourth international symposium: 9-11 April 2003, San Diego, CA, USA.
2003-06
Microbial metabolites of harman alkaloids.
2003-06
11C-harmine as a potential PET tracer for ductal pancreas cancer: in vitro studies.
2003-04
Contribution of individual cytochrome P450 isozymes to the O-demethylation of the psychotropic beta-carboline alkaloids harmaline and harmine.
2003-04
In vitro activity of the beta-carboline alkaloids harmane, harmine, and harmaline toward parasites of the species Leishmania infantum.
2002-06-04
Identification of harman as the antibiotic compound produced by a tunicate-associated bacterium.
2002-01-28
Patents

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.
Name Type Language
BANISTERINE
Preferred Name English
HARMINE
MART.   MI  
Systematic Name English
HARMINE [MI]
Common Name English
YAGEINE
Common Name English
TELEPATHINE
Common Name English
7-METHOXY-1-METHYL-9H-PYRIDO(3,4-B)INDOLE
Systematic Name English
HARMINE [MART.]
Common Name English
LEUCOHARMINE
Common Name English
Classification Tree Code System Code
WIKIPEDIA TiHKAL
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NCI_THESAURUS C667
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Code System Code Type Description
MERCK INDEX
m5919
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PRIMARY Merck Index
CAS
442-51-3
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PRIMARY
FDA UNII
4FHH5G48T7
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PRIMARY
SMS_ID
300000041150
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PRIMARY
WIKIPEDIA
HARMINE
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PRIMARY
EPA CompTox
DTXSID30196066
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PRIMARY
MESH
D006247
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PRIMARY
CHEBI
28121
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PRIMARY
PUBCHEM
5280953
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PRIMARY
ECHA (EC/EINECS)
207-131-4
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PRIMARY
DRUG BANK
DB07919
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PRIMARY
NCI_THESAURUS
C97713
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PRIMARY