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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 Code

13 - Non 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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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
K T Douglas et al.
Molecular pharmacology, 23(3), 614-618 (1983-05-01)
The ionization and UV-visible spectral properties of some harmala alkaloids have been investigated spectrophotometrically. Harmaline and harmine were found to have pKa values of 9.55 +/- 0.04 and 7.45 +/- 0.03, respectively. The ionization of harmalol was characterized by two
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
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
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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