Chemistry: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.[1][2]
Pharmacology
Pharmacodynamics
Ψ-DOM-DragonFLY, a super-potent 5-HT2A receptor agonist with an affinity of 1.8 nM,[1][2][3] It also bound to the 5-HT2C receptor with an affinity of 0.9 nM.[3]
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.[3]
References
- ↑ 1.0 1.1 "Chemistry and Structure–Activity Relationships of Psychedelics". Current Topics in Behavioral Neurosciences. Berlin, Heidelberg: Springer Berlin Heidelberg. 2017. pp. 1–43. ISBN 978-3-662-55878-2.
- ↑ 2.0 2.1 "Structure–activity relationships of serotonin 5-HT2Aagonists". Wiley Interdisciplinary Reviews: Membrane Transport and Signaling 1 (5): 559–579. 2012-02-28. doi:10.1002/wmts.42. ISSN 2190-460X.
- ↑ 3.0 3.1 3.2 "Translocation of the 5-alkoxy substituent of 2,5-dialkoxyarylalkylamines to the 6-position: effects on 5-HT(2A/2C) receptor affinity". Bioorganic & Medicinal Chemistry Letters 12 (15): 1997–1999. August 2002. doi:10.1016/s0960-894x(02)00306-2. PMID 12113827.
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