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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

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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

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
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
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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