6327-54-4

Usage

Chemical class

Phenylmethanones

Type of compound

Synthetic

Psychoactive effects

Potent hallucinogenic

Usage

Recreational drug, substitute for MDMA or ecstasy

Mechanism of action

Stimulates the release of serotonin, acts as a selective serotonin receptor agonist

Effects on mood, perception, and consciousness

Altered

Common forms

Found in party pills or combined with other substances

Adverse effects

Anxiety, nausea, increased heart rate

Legal status

Controlled substance in many countries

Potential for abuse

High due to psychoactive properties

Upstream product

• 477-47-4 picropodophyllotoxin 
• 25054-53-9 3,4-(methylenedioxy)benzoyl chloride 
• 94-53-1 Piperonylic acid 
• 63916-59-6 benzo[d][1,3]dioxol-5-yl(morpholino)methanone 
• 2675-79-8 1-bromo-3,4,5-trimethoxybenzene 
• 7470-99-7 2-(3,4,5-Trimethoxybenzoyl)-4,5-(methylenedioxy)benzoic Acid 
• 274-09-9 Methylenedioxybenzene 
• 4521-61-3 3,4,5-Trimethoxybenzoyl chloride 

Downstream Products

• 102474-37-3 ((Z)-3,4,5-trimethoxy-3',4'-methylenedioxy-benzhydrylidene)-succinic acid 
• 102474-37-3 ((E)-3,4,5-trimethoxy-3',4'-methylenedioxy-benzhydrylidene)-succinic acid 
• 102448-75-9 (RS)-[(SR)-benzo[1,3]dioxol-5-yl-(3,4,5-trimethoxy-phenyl)-methyl]-succinic acid 

Relevant academic research and scientific papers

Synthesis of phenstatin and prodrugs thereof

A newly discovered antineoplastic compound denominated “phenstatin” is herein described as are synthetic methods for producing phenstatin and the active prodrug thereof. Phenstatin was converted to the sodium phosphate prodrug (3d) by a dibenzylphosphite

Antineoplastic agents. 379. Synthesis of phenstatin phosphate

A structure-activity relationship (SAR) study of the South African willow tree (Combretum caffrum) antineoplastic constituent combretastatin A- 4 (1b) directed at maintaining the (Z)stilbene relationship of the olefin diphenyl substituents led to synthesis of a potent cancer cell growth inhibitor designated phenstatin (3b). Initially phenstatin silyl ether (3a) was unexpectedly obtained by Jacobsen oxidation of combretastatin A-4 silyl ether (1c → 3a), and the parent phenstatin (3b) was later synthesized (6a → 3a → 3b) in quantity. Phenstatin was converted to the sodium phosphate prodrug (3d) by a dibenzyl phosphite phosphorylation and subsequent hydrogenolysis sequence (3b → 3c → 3d). Phenstatin (3b) inhibited growth of the pathogenic bacterium Neisseria gonorrhoeae and was a potent inhibitor of tubulin polymerization and the binding of colchicine to tubulin comparable to combretastatin A-4 (1b). Interestingly, the prodrugs were found to have reduced activity in these biochemical assays. While no significant tubulin activity was observed with the phosphorylated derivative of combretastatin A- 4 (1d), phosphate 3d retained detectable inhibitory effects in both assays.