525-72-4

Basic information

• Product Name: 1-methyl-1,2,3,4-tetrahydroisoquinoline-6,7-diol
• Synonyms: (R)-Salsolinol;1-methyl-1,2,3,4-tetrahydroisoquinoline-6,7-diol;Isoquinoline, 1,2,3,4-tetrahydro-6,7-dihydroxy-1-methyl-;[R,(+)]-1-Methyl-1,2,3,4-tetrahydroisoquinoline-6,7-diol;1,2,3,4-Tetrahydro-6,7-dihydroxy-1-methylisoquinoline;1-Methyl-1,2,3,4-tetrahydro-6,7-isoquinolinediol;Sasolinol;1-Methyl-6,7-dihydroxytetrahydroisoquinoline
• CAS NO: 525-72-4
• Molecular Formula: C₁₀H₁₃NO₂
• Molecular Weight: 179.22
• Mol File: 525-72-4.mol

Chemical Properties

• Melting Point: 181-183 °C
• Boiling Point: 362.6°Cat760mmHg
• Flash Point: 175.4°C
• Appearance: /
• Density: 1.201
• PKA: 9.15±0.40(Predicted)
• CAS DataBase Reference: 1-methyl-1,2,3,4-tetrahydroisoquinoline-6,7-diol(CAS DataBase Reference)
• NIST Chemistry Reference: 1-methyl-1,2,3,4-tetrahydroisoquinoline-6,7-diol(525-72-4)
• EPA Substance Registry System: 1-methyl-1,2,3,4-tetrahydroisoquinoline-6,7-diol(525-72-4)

Safety Data

• Hazardous Substances Data: 525-72-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Development:
1-methyl-1,2,3,4-tetrahydroisoquinoline-6,7-diol is used as a pharmaceutical candidate for its potential antioxidant properties, which may help in combating oxidative stress-related conditions. Its anti-inflammatory effects also suggest its use in treating inflammation-based disorders.
Used in Neuroprotective Therapies:
Due to its neuroprotective effects, 1-methyl-1,2,3,4-tetrahydroisoquinoline-6,7-diol is considered for use in neurodegenerative disease treatments, aiming to protect neurons from damage and potentially slow disease progression.
Further studies are necessary to explore and validate the therapeutic applications of 1-methyl-1,2,3,4-tetrahydroisoquinoline-6,7-diol across various medical fields, ensuring its safety and efficacy in clinical settings.

Upstream product

• 493-48-1 (6,7-dimethoxy-1-methyl-1,2,3,4-tetrahydroisoquinoline) 
• 51-61-6 dopamine 
• 75-07-0 acetaldehyde 
• 62-31-7 dopamine hydrochloride 
• 63283-42-1 6,7-dimethoxy-1-methyl-1,2,3,4-tetrahydroisoquinoline hydrochloride 

Downstream Products

• 1581289-05-5 C₁₆H₁₅N₃O₈S 
• 1581289-14-6 C₁₆H₁₅N₃O₈S 
• 1581289-16-8 C₁₈H₁₅F₆NO₄S 
• 114561-80-7 2-benzyl-6,7-bis-benzyloxy-1-methyl-1,2,3,4-tetrahydro-isoquinoline 
• 4593-97-9 N-Nor-1-methylcorypalline 
• 19641-12-4 6-methoxy-1,2-dimethyl-1,2,3,4-tetrahydroisoquinolin-7-ol 
• 89-31-6 rac-salsoline 
• 51-61-6 dopamine 
• 53405-13-3 1,2,3,4-tetrahdyro-1-methylisopquinoline-7,8-diol 
• 65644-76-0 (+/-)-N-Methylsalsoline 
• 490-53-9 (+/-)-carnegine 
• 493-48-1 (6,7-dimethoxy-1-methyl-1,2,3,4-tetrahydroisoquinoline) 

Relevant articles and documents

Method for separating and purifying water-soluble catechol type tetrahydroisoquinoline alkaloid by using macroporous resin

The invention provides a method for separating and purifying water-soluble catechol type tetrahydroisoquinoline alkaloid by using a macroporous resin, wherein the water-soluble catechol type tetrahydroisoquinoline alkaloid has a structure represented by a

NEW USE OF ISOQUINOLINE DERIVATIVES FOR WOUND HEALING

The present invention is related to a method for wound healing comprising administering to a subject in need thereof a pharmaceutical composition comprising a pharmaceutically acceptable carrier and a therapeutically effective amount of a compound having the general Formula I, preferably salsolinol.

Synthesis, Purification, and Selective β2-AR Agonist and Bronchodilatory Effects of Catecholic Tetrahydroisoquinolines from Portulaca oleracea

A green, biomimetic, phosphate-mediated Pictet-Spengler reaction was used in the synthesis of three catecholic tetrahydroisoquinolines, 1, 2, and 12, present in the medicinal plant Portulaca oleracea, as well as their analogues 3-11, 13, and 14, with dopa

Monitoring on-chip pictet-spengler reactions by integrated analytical separation and label-free time-resolved fluorescence

High-throughput screening for optimal reaction conditions and the search for efficient catalysts is of eminent importance in the development of chemical processes and for expanding the spectrum of synthetic methodologies in chemistry. In this context we report a novel approach for a microfluidic chemical laboratory integrating organic synthesis, separation and time-resolved fluorescence detection on a single microchip. The feasibility of our integrated laboratory is demonstrated by monitoring the formation of tetrahydroisoquinoline derivatives by Pictet-Spengler condensation. After on-chip reaction the products and residual starting material were separated enantioselectively on the same chip. On-chip deep UV laser-induced fluorescence detection with time-correlated single photon counting was applied for compound assignment. The system was utilized to screen reaction conditions and various substrates for Pictet-Spengler reactions on-chip. Finally, the microlab was successfully applied to investigate enantioselective reactions using BINOL-based phosphoric acids as organocatalysts. Chip trick: An integrated chip-based approach for rapid monitoring of organic synthesis at the microscale level is presented. This is achieved by the integration of microfluidic channels for reaction and electrophoresis on a single device together with time-correlated single-photon counting for compound identification (see figure). Copyright

Phosphate mediated biomimetic synthesis of tetrahydroisoquinoline alkaloids

A one-pot synthesis of tetrahydroisoquinoline alkaloids in a phosphate buffer has been achieved, and a reaction mechanism proposed. The utilisation of mild reaction conditions readily afforded a range of isoquinolines, including norcoclaurine.

Starburst Conjugates of Proteins with Carbon-Chain Polymers Containing Low Molecular Biologically Active Compounds: Synthesis and Immunogenicity

The synthesis of starburst polymer-protein conjugates on the basis of bovine serum albumin and horseradish peroxidase was performed with the aim to study the possibilities of regulation of the immune response against the components of the conjugates. These polymers had one-point binding between the protein and the modifying carbon-chain polymer that contained 1-vinyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline (a salsolinol analogue) or bradykinin (peptide hormone) residues in its carbon chain. Changes in the chemical nature of the carbon-chain part of the polymer-protein conjugate were shown to increase or decrease the level of antibody production both against the low-molecular compounds attached to the polymeric fragments and against the protein carrier.

Preparation of Unstable Quinones in Aqueous Solution via Pulse Radiolytic One-electron Oxidation of Dihydroxybenzenes

The stoichiometry of the reactions of semiquinones resulting from the one-electron oxidation of various dihydroxybenzenes is examined.It is verified that the semiquinones of hydroquinone and catechol disproportionate completely to give p-benzoquinone and o-benzoquinone, respectively.With resorcinol, however, the corresponding semioxidised radical reaction is different, giving unstable dimers which subsequently rearrange to tetrahydroxybiphenyls.The usefulness of catechol one-electron oxidation followed by o-semiquinone disproportionation as a means of preparing biologically important unstable o-quinones is exemplified by three new examples: (1) The o-quinone of oestradiol which may have melanocytotoxic properties; (2) the o-quinone of salsolinol whose oxidative metabolites may be responsible for neuronal damage in alcoholism and (3) o-quinone of tetrahydropapaveroline whose oxidative metabolism may play a role in both alcohol addiction and Parkinson's disease.

METABOLISM OF SALSOLINOL BY TISSUE CULTURES OF SOME PAPAVERACEAE

(+/-)-Salsolinol, a substance possibly inducing Parkinsonism and alcoholism, was transformed into the 6- and 7-O-monomethylated salsolinols by various plant tissue cultures of Papaveraceae.Only 6-O-methylsalsolinol was further N-methylated to provide N-methylisosalsoline.Key Word Index - Corydalis ochotensis; C. opliocarpa; Macleaya cordata; Papaveraceae; tissue cultures; metabolism; isoquinoline alkaloid; salsolinol.

Actions of two dopamine derivatives at adreno- and cholinoceptors

Salsolinol (1) and 6,7-dihydroxy-1,1-dimethyl-1,2,3,4-tetrahydroisoquinoline hydrobromide (2) were synthesized and their effects at adreno- and cholinoceptors investigated both in vivo and in vitro. Both 1 and 2 produced agonist effects at cholinoceptors and α- and β-adrenoceptors. Neuromuscular blocking actions were evident in vitro. Compound 2 exhibited anticholinesterase properties both in vivo and in vitro. These results indicate that dopamine derivatives of this type exhibit not only sympathomimetic activity but also complex actions at cholinoceptors.