883-87-4

Basic information

• Product Name: 6,7-DIMETHOXY-1-METHYL-1,2,3,4-TETRAHYDROISOQUINOLINE HYDROCHLORIDE
• Synonyms: 6,7-DIMETHOXY-1-METHYL-1,2,3,4-TETRAHYDROISOQUINOLINE HYDROCHLORIDE;SALSOLIDINE HYDROCHLORIDE;(S)-1,2,3,4-tetrahydro-6,7-dimethoxy-1-methylisoquinolinium chloride;(1S)-6,7-dimethoxy-1-methyl-1,2,3,4-tetrahydroisoquinoline hydrochloride
• CAS NO: 883-87-4
• Molecular Formula: C₁₂H₁₈NO₂*Cl
• Molecular Weight: 243.73
• EINECS: 212-934-8
• Product Categories: Alkaloids
• Mol File: 883-87-4.mol
• Article Data: 1

Chemical Properties

• Melting Point: 189-192 °C
• Boiling Point: 313.4 °C at 760 mmHg
• Flash Point: 127.1 °C
• Appearance: /
• Vapor Pressure: 0.000496mmHg at 25°C
• CAS DataBase Reference: 6,7-DIMETHOXY-1-METHYL-1,2,3,4-TETRAHYDROISOQUINOLINE HYDROCHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 6,7-DIMETHOXY-1-METHYL-1,2,3,4-TETRAHYDROISOQUINOLINE HYDROCHLORIDE(883-87-4)
• EPA Substance Registry System: 6,7-DIMETHOXY-1-METHYL-1,2,3,4-TETRAHYDROISOQUINOLINE HYDROCHLORIDE(883-87-4)

Safety Data

• Hazard Codes: Xn
• Statements: 36/37/38-22
• Safety Statements: 37/39-26
• Hazardous Substances Data: 883-87-4(Hazardous Substances Data)

Usage

General Description

6,7-DIMETHOXY-1-METHYL-1,2,3,4-TETRAHYDROISOQUINOLINE HYDROCHLORIDE, also known as DMTHIQ, is a chemical compound with potential pharmacological properties. It is a derivative of tetrahydroisoquinoline and is often used in research as a precursor for the synthesis of various bioactive compounds. DMTHIQ has been studied for its potential as a therapeutic agent in the treatment of neurological disorders, including Parkinson's disease and addiction. It acts on the central nervous system and has shown to have neuroprotective and neurorestorative effects in preclinical studies. Additionally, it has been investigated for its potential role in modulating dopamine release and reuptake, making it a promising compound for further research and development in the field of neuropharmacology.

InChI:InChI=1/C12H17NO2.ClH/c1-8-10-7-12(15-3)11(14-2)6-9(10)4-5-13-8;/h6-8,13H,4-5H2,1-3H3;1H/t8-;/m0./s1

Upstream product

• 4721-98-6 6,7-dimethoxy-1-methyl-3,4-dihydroisoquinoline 

Downstream Products

• 65140-22-9 (S)-(+)-Carnegine hydrochloride 

Relevant articles and documents

Stereoselectivity and Structural Characterization of an Imine Reductase (IRED) from Amycolatopsis orientalis

The imine reductase AoIRED from Amycolatopsis orientalis (Uniprot R4SNK4) catalyzes the NADPH-dependent reduction of a wide range of prochiral imines and iminium ions, predominantly with (S)-selectivity and with ee's of up to >99%. AoIRED displays up to 100-fold greater catalytic efficiency for 2-methyl-1-pyrroline (2MPN) compared to other IREDs, such as the enzyme from Streptomyces sp. GF3546, which also exhibits (S)-selectivity, and thus, AoIRED is an interesting candidate for preparative synthesis. AoIRED exhibits unusual catalytic properties, with inversion of stereoselectivity observed between structurally similar substrates, and also, in the case of 1-methyl-3,4-dihydroisoquinoline, for the same substrate, dependent on the age of the enzyme after purification. The structure of AoIRED has been determined in an "open" apo-form, revealing a canonical dimeric IRED fold in which the active site is formed between the N- and C-terminal domains of participating monomers. Co-crystallization with NADPH gave a "closed" form in complex with the cofactor, in which a relative closure of domains, and associated loop movements, has resulted in a much smaller active site. A ternary complex was also obtained by cocrystallization with NADPH and 1-methyl-1,2,3,4-tetrahydroisoquinoline [(MTQ], and it reveals a binding site for the (R)-amine product, which places the chiral carbon within 4 ? of the putative location of the C4 atom of NADPH that delivers hydride to the C? -N bond of the substrate. The ternary complex has permitted structure-informed mutation of the active site, resulting in mutants including Y179A, Y179F, and N241A, of altered activity and stereoselectivity.