2-Methyl-β-carboline, 1-Methyl-9H-pyrido[3,4-b]indole, Aribine
Empirical Formula (Hill Notation):
CAS Number:
Molecular Weight:
Beilstein/REAXYS Number:
EC Number:
MDL number:
PubChem Substance ID:
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Quality Level



drug control

stupéfiant (France)


235-238 °C (lit.)


methanol: soluble 50mg/ml

SMILES string




InChI key


Gene Information

human ... CYP2D6(1565)
rat ... Gabra2(29706)

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General description

  • Harmane is a potent tremor-producing β-carboline alkaloid and neurotoxin.
  • It is major representative of heterocyclic aromatic amines, a group of mutagenic and carcinogenic substances which are formed in meat from the precursors creatine, creatinine, amino acids and sugars during the heating at high temperatures.
  • Blood harmane concentration is elevated in essential tremor, late-life neurological disease.


  • Harmane was used in trace level determination of harmane by planar chromatography coupled with (tandem) mass spectrometry.
  • It was used to study interactions of norharman and harman with DNA.
  • It may be used as matrix for analysis of cyclodextrins and for sulfated oligosaccharides in combination with DHB as co-matrix.


1 g in glass bottle

Biochem/physiol Actions

I1 imidazoline binding site agonist.

Preparation Note

Harmane dissolves in methanol at a concentration of 50mg/ml to form a clear, colourless to yellow solution.

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves


NONH for all modes of transport

WGK Germany


Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Ingrid Bacher et al.
Archives of general psychiatry, 68(8), 817-826 (2011-08-04)
Greater prefrontal cortex and anterior cingulate cortex monoamine oxidase A (MAO-A) binding is associated with depressed mood. Substances in cigarette smoke, such as harman, inhibit MAO-A, and cigarette withdrawal is associated with depressed mood. Dysphoria during cigarette withdrawal predicts relapse....
Mohamed A M El Gendy et al.
Toxicology and applied pharmacology, 249(1), 55-64 (2010-08-25)
Harman is a common compound in several foods, plants and beverages. Numerous studies have demonstrated its mutagenic, co-mutagenic and carcinogenic effects; however, the exact mechanism has not been fully identified. Aryl hydrocarbon receptor (AhR) is a transcription factor regulating the...
Elan D Louis et al.
Neurotoxicology, 29(2), 294-300 (2008-02-05)
Essential tremor (ET) is a widespread late-life neurological disease. Genetic and environmental factors likely play an etiological role. Harmane (1-methyl-9H-pyrido[3,4-b]indole) is a potent tremor-producing neurotoxin. In 2002, we demonstrated elevated blood harmane concentrations in an initial sample of 100 ET...
Marisa Till et al.
Journal of natural products, 72(4), 796-798 (2009-02-18)
A new alkaloid, 5-bromo-8-methoxy-1-methyl-beta-carboline (1), has been isolated from the New Zealand marine bryozoan Pterocella Vesiculosa. Structural elucidation was achieved through NMR spectroscopic and mass spectrometric analysis, and a single-crystal X-ray diffraction analysis of 1 was performed. The biological activity...
Bijan Kumar Paul et al.
The journal of physical chemistry. B, 115(34), 10322-10334 (2011-07-28)
The present work describes the interaction of a promising cancer cell photosensitizer, harmane (HM), with a model transport protein, Bovine Serum Albumin (BSA). The studied molecule of interest (HM) belongs to the family of naturally occurring fluorescent drug-binding alkaloids, the...
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