103276

Sigma-Aldrich

Harmane

98%

Synonym(s):
2-Methyl-β-carboline, 1-Methyl-9H-pyrido3,4-bindole, Aribine
Empirical Formula (Hill Notation):
C12H10N2
CAS Number:
Molecular Weight:
182.22
Beilstein/REAXYS Number:
143898
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22
Pricing and availability is not currently available.

Quality Level

assay

98%

drug control

stupéfiant (France)

mp

235-238 °C (lit.)

solubility

methanol: soluble 50mg/ml

SMILES string

Cc1nccc2c3ccccc3nHc12

InChI

1S/C12H10N2/c1-8-12-10(6-7-13-8)9-4-2-3-5-11(9)14-12/h2-7,14H,1H3

InChI key

PSFDQSOCUJVVGF-UHFFFAOYSA-N

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.

Application

  • 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.

Packaging

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

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Mohammad Nasehi et al.
Journal of psychopharmacology (Oxford, England), 26(8), 1151-1161 (2011-10-04)
β-carboline alkaloids such as harmane (HA) are naturally present in the human food chain. They are derived from the plant Peganum harmala and have many cognitive effects. In the present study, effects of the nicotinic system of the dorsal hippocampus...
Bijan Kumar Paul et al.
The journal of physical chemistry. B, 115(41), 11938-11949 (2011-09-09)
The present study aims at exploring a detailed characterization of the binding interaction of a promising cancer cell photosensitizer, harmane (HM), with DNA extracted from herring sperm. The polarity-sensitive prototropic transformation of HM, a naturally occurring, fluorescent, drug-binding alkaloid, β-carboline...
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...
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...
Ute Jautz et al.
Journal of chromatography. A, 1128(1-2), 244-250 (2006-07-28)
HPTLC/MS by a plunger-based extraction device was shown to be an appropriate technique for quantitative planar chromatography, even in trace analysis. Reproducible extraction from silica gel phases in the lower-pg range distinguishes this technique from other approaches. Repeatability of the...
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