75877-72-4

Usage

Uses

Used in Pharmaceutical Industry:
7,8-Dimethoxy-3,4-dihydroisoquinoline is used as a key intermediate in the synthesis of Tetrabenazine (T28400), a dopamine-depleting agent. 7,8-dimethoxy-3,4-dihydroisoquinoline is employed for its antidyskinetic and antipsychotic properties, making it a valuable component in the development of medications for the treatment of movement disorders and psychiatric conditions.

InChI:InChI=1/C11H13NO2/c1-13-10-4-3-8-5-6-12-7-9(8)11(10)14-2/h3-4,7H,5-6H2,1-2H3

Upstream product

• 52759-08-7 1,2,3,4-tetrahydro-7,8-dimethoxyisoquinoline 
• 120-20-7 2-(3,4-dimethoxyphenyl)-ethylamine 
• 68-12-2 N,N-dimethyl-formamide 

Relevant academic research and scientific papers

Preparation of 7,8-dimethoxy-3,4-dihydroisoquinolines, facile route to 7-8-dioxygenated-3,4-dihydroisoquinolines

Oxidation of 7,8-dimethoxy-1,2,3,4-tetrahydroisoquinoline with potassium permanganate in acetone afforded 7,8-dimethoxy-3,4-dihydroisoquinoline as the primary product. Hence, oxidation of the appropriate secondary nonphenolic 7,8-dioxygenated tetrahydroisoquinoline alkaloid is thus a facile method for the generation of the corresponding imine. The imine is not easily prepared via the usual synthetic route involving ring closure of β-phenethylamine derivatives.

Decahydro-8H-isoquino[2,1-g][1,6]naphthyridine and decahydrobenzo[a]pyrrolo [2,3-e]quinolizine derivatives

Compounds of the formula STR1 wherein: m is an integer of 1-6;n is an integer of 1 or 2;X and Y are independently hydrogen; hydroxy; lower alkyl; lower alkoxy; or halo; or X and Y when adjacent and taken together are methylenedioxy or ethylene-1,2-dioxy;R is STR2 wherein: R 1 and R 2 are independently hydrogen or lower alkyl, or when taken together with the carbon to which they are attached are cycloalkyl;R 3 is hydrogen, lower alkyl, lower alkoxy, hydroxy, trifluoromethyl or halo; and STR3 and pharmaceutically acceptable acid addition salts thereof. The compounds and salts exhibit useful pharmacological properties, including selective α 2 -adrenoceptor antagonist properties and 5-HT 1A receptor partial agonist properties, and are particularly useful for the treatment of sexual dysfunction, depression and anxiety.

Decahydro-8H-isoquino[2,1-g][1,6]naphthyridine and decahydrobenzo[a]pyrrolo[2,3-e]quinolizine derivatives

Compounds of the formula ψψ ψwherein:ψ X and Y are independently hydrogen; hydroxy; lower alkyl of 1-6 carbon atoms; lower alkoxy of 1-6 carbon atoms; or halo; or X and Y when adjacent and taken together are methylenedioxy or ethylene-1,2-dioxy;ψ R is lower alkyl of 1-6 carbon atoms; cycloalkyl of 3-8 carbon atoms; phenyl or phenyl lower alkyl in which any phenyl group may be optionally substituted by one or two substituents chosen from the group consisting of halo, lower alkyl of 1-4 carbon atoms and lower alkoxy of 1-4 carbon atoms; or -ANHSO2R1; wherein A is lower alkylene of 1-6 carbon atoms; and R1 is lower alkyl of 1-6 carbon atoms or -NRyR3; whereinψ Ry and R3 are independently hydrogen or lower alkyl of 1-6 carbon atoms, or Ry and R3 taken together are cycloalkyl of 3-8 carbon atoms; andψ n is 1 or 2;ψ and the pharmaceutically acceptable salts thereof, are useful as à2-adrenoceptor antagonists, in particular as peripherally selective à2 -adrenoceptor antagonists.ψ

REGIOSELECTIVE SYNTHESIS OF 7,8-DIOXYGENATED-3,4-DIHYDROISOQUINOLINES BY METALATION OF β-PHENETHYLAMINES

A new, one-pot procedure for the synthesis of the title compounds is described which is based on the thermodynamic metalation of the corresponding β-(3,4-dialkoxyphenyl)ethylamine.