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103276

Sigma-Aldrich

Harmane

98%

Sinónimos:

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

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About This Item

Fórmula empírica (notación de Hill):
C12H10N2
Número de CAS:
486-84-0
Peso molecular:
182.22
Beilstein/REAXYS Number:
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

signalword

Warning

hcodes

H302,H315

Hazard Classifications

Acute Tox. 4 Oral - Skin Irrit. 2

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificados de análisis (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

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
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
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.
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