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:
Product Name
Harmane, 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)
mp
235-238 °C (lit.)
solubility
methanol: soluble 50mg/ml
Quality Level
Gene Information
human ... CYP2D6(1565)
rat ... Gabra2(29706)
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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.
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.
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
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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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
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
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(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
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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