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Key Documents

103276

Sigma-Aldrich

Harmane

98%

Synonyme(s) :

1-Methyl-9H-pyrido[3,4-b]indole, 2-Methyl-β-carboline, Aribine

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About This Item

Formule empirique (notation de Hill):
C12H10N2
Numéro CAS:
Poids moléculaire :
182.22
Numéro Beilstein :
143898
Numéro CE :
Numéro MDL:
Code UNSPSC :
12352100
ID de substance PubChem :
Nomenclature NACRES :
NA.22

Pureté

98%

drug control

stupéfiant (France)

Pf

235-238 °C (lit.)

Solubilité

methanol: soluble 50mg/ml

Chaîne SMILES 

Cc1nccc2c3ccccc3[nH]c12

InChI

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

Clé InChI

PSFDQSOCUJVVGF-UHFFFAOYSA-N

Informations sur le gène

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

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Description générale

  • 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.

Actions biochimiques/physiologiques

I1 imidazoline binding site agonist.

Notes préparatoires

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

Pictogrammes

Exclamation mark

Mention d'avertissement

Warning

Mentions de danger

Classification des risques

Acute Tox. 4 Oral - Skin Irrit. 2

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)


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Les clients ont également consulté

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
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
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
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.
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

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