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H125

Sigma-Aldrich

Harmalol hydrochloride dihydrate

monoamine oxidase inhibitor

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About This Item

Empirical Formula (Hill Notation):
C12H12N2O · HCl · 2H2O
CAS Number:
6028-00-8
Molecular Weight:
272.73
EC Number:
227-898-9
MDL number:
MFCD00150053
UNSPSC Code:
12352200
PubChem Substance ID:
24895441

drug control

regulated under CDSA - not available from Sigma-Aldrich Canada

mp

264-267 °C (dec.) (lit.)

SMILES string

Cl[H].[H]O[H].[H]O[H].CC1=NCCc2c1[nH]c3cc(O)ccc23

InChI

1S/C12H12N2O.ClH.2H2O/c1-7-12-10(4-5-13-7)9-3-2-8(15)6-11(9)14-12;;;/h2-3,6,14-15H,4-5H2,1H3;1H;2*1H2

InChI key

OYKGNQNESCZSHQ-UHFFFAOYSA-N

Biochem/physiol Actions

Harmalol, a harmala (β-carboline) alkaloid, is a monoamine oxidase inhibitor (MAOi) useful for studies involving melanogenesis. Harmalol is use in β-carboline nucleic acid (DNA and RNA) binding studies.

Storage Class

13 - Non Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

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Ji-Hyun Im et al.
Vascular pharmacology, 50(5-6), 147-152 (2008-12-17)
Beta-carboline alkaloids including harmalol, harmaline, norharmane, harmol, harmine and harmane are important constituents of the medicinal plant, Perganum harmala L. (Zygophylaceae), which has been used in traditional medicine. In the present study, the antiplatelet activities of six beta-carboline alkaloid compounds
C S Lee et al.
Journal of neurochemistry, 75(2), 521-531 (2000-07-19)
The present study elucidated the protective effect of beta-carbolines (harmaline, harmalol, and harmine) on oxidative neuronal damage. MPTP treatment increased activities of total superoxide dismutase, catalase, and glutathione peroxidase and levels of malondialdehyde and carbonyls in the basal ganglia, diencephalon
T A Al-Alaf et al.
Journal of inorganic biochemistry, 38(1), 47-56 (1990-01-01)
The preparation of novel biologically active platinum(II) and palladium(II) complexes of some beta-carboline alkaloids (harmaline, harmalol, harmine, and harmane) is described. These complexes, characterized on the basis of their CHN elemental analysis, infrared, Raman and 1H and 13C nuclear resonance
P Rivas et al.
Comparative biochemistry and physiology. Part C, Pharmacology, toxicology & endocrinology, 122(1), 27-31 (1999-04-06)
Several beta-carboline (9H-pyrido-[3,4-b]-indole) alkaloids were evaluated for in vitro trypanosomicidal activity against Trypanosoma cruzi epimastigotes belonging to two different strains (Tulahuén and LQ) showing different sensitivity to nifurtimox. Important differences were observed in the susceptibility of the parasites to these
D H Kim et al.
The European journal of neuroscience, 13(10), 1861-1872 (2001-06-14)
The present study elucidated the protective effect of beta-carbolines (harmaline, harmalol and harmine) against oxidative damage of brain mitochondria, synaptosomes and PC12 cells induced by either dopamine or 6-hydroxydopamine. Harmaline, harmalol and antioxidant enzymes (superoxide dismutase/SOD and catalase) decreased the
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