73177-38-5

Usage

Uses

Used in Research Applications:
2,5-Dimethoxy-1-(3-methoxy-benzyl)-cyclohexa-2,5-dienecarboxylic acid is utilized as a research chemical for studying the mechanisms of action and effects of psychedelic substances on the human brain. Its role as a serotonin receptor agonist makes it a valuable tool in understanding the neurobiological underpinnings of hallucinations and altered states of consciousness.
Used in Pharmaceutical Development:
In the pharmaceutical industry, 2,5-Dimethoxy-1-(3-methoxy-benzyl)-cyclohexa-2,5-dienecarboxylic acid serves as a lead compound for the development of new medications targeting mental health disorders. Its interaction with serotonin receptors suggests potential therapeutic applications in treating conditions such as depression, anxiety, and post-traumatic stress disorder (PTSD), where modulation of serotonin signaling may be beneficial.
Used in Psychedelic Therapy:
2,5-Dimethoxy-1-(3-methoxy-benzyl)-cyclohexa-2,5-dienecarboxylic acid is employed in psychedelic therapy as a means to facilitate deep introspection and emotional processing. Its powerful hallucinogenic effects can help individuals confront and resolve psychological issues, fostering personal growth and healing.

Upstream product

• 2785-98-0 2,5-dimethoxybenzoic acid 
• 874-98-6 1-bromomethyl-3-methoxybenzene 
• 80900-48-7 C₉H₁₀O₄^(2-)*2Li⁽¹⁺⁾ 

Relevant academic research and scientific papers

The total synthesis of the galbulimima alkaloid GB 13

This contribution describes a synthetic approach to alkaloid GB 13, previously isolated from the North Australian and Papua New Guinean rain forest tree Galbulimima belgraveana. A Birch reductive alkylation of 2,5-dimethoxybenzoic acid by 3-methoxybenzyl bromide, followed by an acid-catalyzed cyclization was used to synthesize the [3.3.1]bicyclononane 8. A ring contraction performed on the diazo derivative 9 of the [3.3.1]bicyclononane led to [3.2.1]bicyclooctane 10. This [3.2.1]bicyclooctane was converted into a dienophile and subjected to a Diels-Alder reaction to generate a pentacyclic intermediate 13 with a carbon skeleton closely resembling the target alkaloid. The surplus substituent, required for activation and regioselectivity in the Diels-Alder reaction, was removed using Birch reductive conditions to effect a decyanation. It was discovered that a Birch reduction of the aromatic ring also present in the molecule could be performed at the same time to give the enone 15, which was cleaved by means of an Eschenmoser fragmentation. The piperidine ring found in the natural product was formed by reductive cyclization of the bis-oxime 18 derived from the alkynyl ketone 17 and the resulting material further elaborated to GB 13 (1) via ketone 20. Copyright

Reductive Alkylation of 2,5-Dimethoxybenzoic Acid: A Direct Synthesis of Dihydrofluoren-2-ones

A two-operation procedure is described for the synthesis of 3,4-dihydrofluoren-2(1H)-ones from "reductive alkylation" of 2,5-dimethoxybenzoic acid with benzyl halides, followed by cyclodehydration of the adducts, with concomitant decarboxylation.