525-57-5

Basic information

• Product Name: HARMALOL
• Synonyms: 3,4-DIHYDRO-7-HYDROXY-1-METHYL-BETA-CARBOLINE;HARMALOL;TIMTEC-BB SBB005350;HARMALOL(EXTRACTFROMPEGANUMHARMALAROOTS);3H-Pyrido(3,4-B)indol-7-ol, 4,9-dihydro-1-methyl- (8ci)(9ci);6028-07-5 (Hydrochloride);Einecs 208-375-4;Harmidol
• CAS NO: 525-57-5
• Molecular Formula: C₁₂H₁₂N₂O
• Molecular Weight: 200.24
• EINECS: 208-375-4
• Mol File: 525-57-5.mol
• Article Data: 1

Chemical Properties

• Melting Point: 211-212°C
• Boiling Point: 507.5°Cat760mmHg
• Flash Point: 231°C
• Appearance: /
• Density: 1.37
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.708
• CAS DataBase Reference: HARMALOL(CAS DataBase Reference)
• NIST Chemistry Reference: HARMALOL(525-57-5)
• EPA Substance Registry System: HARMALOL(525-57-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-27-36/37/39
• Hazardous Substances Data: 525-57-5(Hazardous Substances Data)

Usage

Description

HARMALOL is a harmala alkaloid with a hydroxy-substituted harman skeleton at the C-7 position and a reduced 3,4 bond. It is a naturally occurring compound with potential applications in various industries.

Uses

Used in Pharmaceutical Industry:
HARMALOL is used as a pharmaceutical agent for its potential therapeutic properties. Its unique chemical structure allows it to interact with various biological targets, making it a promising candidate for the development of new drugs.
Used in Cosmetic Industry:
HARMALOL is used as a cosmetic ingredient for its potential skin care benefits. Its ability to interact with biopolymers and macromolecules may contribute to improved skin health and appearance.
Used in Food Industry:
HARMALOL is used as a food additive for its potential flavor and preservative properties. Its unique chemical structure may contribute to enhanced taste and shelf life of food products.
Used in Agricultural Industry:
HARMALOL is used as a pesticide or herbicide for its potential ability to control pests and weeds. Its interaction with biopolymers and macromolecules may help in the development of more effective and environmentally friendly agricultural solutions.

InChI:InChI=1/C12H12N2O/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

Upstream product

• 304-21-2 harmaline 
• 442-51-3 harmine 

Relevant articles and documents

Contribution of individual cytochrome P450 isozymes to the O-demethylation of the psychotropic β-carboline alkaloids harmaline and harmine

The psychotropic β-carboline alkaloids, showing high affinity for 5-hydroxytryptamine, dopamine, benzodiazepine, and imidazoline receptors and the stimulation of locus coeruleus neurons, are formed endogenously from tryptophan-derived indolealkylamines through the Pictet-Spengler condensation with aldehydes in both plants and mammals. Cytochromes P450 1A1 (18.5), 1A2 (20), and 2D6 (100) catalyzed the O-demethylation of harmaline, and CYP1A1 (98.5), CYP1A2 (35), CYP2C9 (16), CYP2C19 (30), and CYP2D6 (115) catalyzed that of harmine (relative activities). The dehydrogenation/aromatization of harmaline to harmine was not carried out by aromatase (CYP19), CYP1A2, CYP2C9, CYP2D6, CYP3A4, pooled recombinant cytochromes P450, or human liver microsomes (HLMs). Kinetic parameters were calculated for the O-demethylations mediated by each isozyme and by pooled HLMs. Kcat (min-1) and Km (μM) values for harmaline were: CYP1A1, 10.8 and 11.8; CYP1A2, 12.3 and 13.3; CYP2C9, 5.3 and 175; CYP2C19, 10.3 and 160; and CYP2D6, 39.9 and 1.4. Values for harmine were: CYP1A1, 45.2 and 52.2; CYP1A2, 9.2 and 14.7; CYP2C9, 11.9 and 117; CYP2C19, 21.4 and 121; and CYP2D6, 29.7 and 7.4. Inhibition studies using monoclonal antibodies confirmed that CYP1A2 and CYP2D6 were the major isozymes contributing to both harmaline (20% and 50%, respectively) and harmine (20% and 30%) O-demethylations in pooled HLMS. The turnover numbers for CYP2D6 are among the highest ever reported for a CYP2D6 substrate. Finally, CYP2D6-transgenic mice were found to have increased harmaline and harmine O-demethylase activities as compared with wild-type mice. These findings suggest a role for polymorphic CYP2D6 in the pharmacology and toxicology of harmine and harmaline.