Ψ-DOM-DragonFLY

Ψ-DOM-DragonFLY (ψ-DOM-DFLY) also known as the Me-3.5-IDFLY it is a putative serotonergic psychedelic from the FLY class; it is a derivative of DragonFLY and, to some extent, of 2,5-dimethoxy-4-methylamphetamine and 2,6-dimethoxy-4-methylamphetamine, with a different arrangement of the methoxy groups.

Pharmacology

Pharmacodynamics Ψ-DOM-DragonFLY, a super-potent 5-HT2A receptor agonist with an affinity of 1.8 nM, It also bound to the 5-HT2C receptor with an affinity of 0.9 nM.

Сhemistry

Synthesis The synthesis of Ψ-DOM-DragonFLY began with the dialkylation of orcinol using 1-bromo-2-chloroethane and potassium carbonate in acetone; the resulting intermediate was subjected to aromatic dibromination and then to Grignard conditions to close the ring and yield the substituted tetrahydrobenzo ([1,2-b:4,5-’])difuran. This was then regioselectively lithiated at the ortho position; the resulting anion was treated to yield an aldehyde, and the intermediate aldehyde was treated to catalyse a Knövenagel condensation, yielding a nitroalkene, which was subsequently treated with DDQ (2,3-dichloro-5,6-dicyano-1,4-benzoquinone) in dioxane to yield the fully aromatised nitroalkene. This nitroalkene was then reduced with sodium aluminium hydride to Ψ-DOM-DragonFLY.

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