103276
Harmane
98%
Synonym(s):
1-Methyl-9H-pyrido[3,4-b]indole, 2-Methyl-β-carboline, Aribine
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About This Item
Empirical Formula (Hill Notation):
C12H10N2
CAS Number:
Molecular Weight:
182.22
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
EC Number:
207-642-2
Beilstein/REAXYS Number:
143898
MDL number:
Assay:
98%
InChI key
PSFDQSOCUJVVGF-UHFFFAOYSA-N
InChI
1S/C12H10N2/c1-8-12-10(6-7-13-8)9-4-2-3-5-11(9)14-12/h2-7,14H,1H3
SMILES string
Cc1nccc2c3ccccc3[nH]c12
assay
98%
drug control
stupéfiant (France)
Quality Level
Gene Information
human ... CYP2D6(1565)
rat ... Gabra2(29706)
solubility
methanol: soluble 50mg/ml
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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.
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.
signalword
Warning
hcodes
Hazard Classifications
Acute Tox. 4 Oral - Skin Irrit. 2
Storage Class
11 - Combustible Solids
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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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
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
K Hayashi et al.
Nucleic acids research, 4(11), 3679-3685 (1977-11-01)
The interactions of norharman (9H-pyrido [3,4-b] indole) and harman (1-methyl-9H-pyrido [3,4-b] indole) with DNA were studied. DNA caused remarkable fluorescence quenching and change in the absorption spectra of the dyes. Scatchard plots obtained by optical titration gave Kd values of
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