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103276

Sigma-Aldrich

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:
486-84-0
Molecular Weight:
182.22
Beilstein:
143898
EC Number:
207-642-2
MDL number:
MFCD00004957
UNSPSC Code:
12352100
PubChem Substance ID:
24846602
NACRES:
NA.22

Quality Level

100

Assay

98%

drug control

stupéfiant (France)

mp

235-238 °C (lit.)

solubility

methanol: soluble 50mg/ml

SMILES string

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

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.

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.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302,H315

Hazard Classifications

Acute Tox. 4 Oral - Skin Irrit. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCJ7413
BCCF2503
BCBZ8150
BCBZ7222
BCBS3530V

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2,3,4,5-Tetrahydro-1H-pyrido[4,3-b]indole AldrichCPR

Sigma-Aldrich

CBR00326

2,3,4,5-Tetrahydro-1H-pyrido[4,3-b]indole

FINDY ≥98% (HPLC)

Sigma-Aldrich

SML1733

FINDY

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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