Methylene shuffle

The methylene shuffle is a strategy in medicinal chemistry used to modify the hydrophobicity of a compound.^[1][2][3] It involves shortening one alkyl chain by one carbon unit and lengthening another alkyl chain by one carbon unit.^[1][2]

Example of the methylene shuffle: LSD and MiPLA

• 
  LSD
• 
  MiPLA

An example of the methylene shuffle is the structural modification of the psychedelic drug lysergic acid diethylamide (LSD), which has N,N-diethyl groups, into methylisopropyllysergamide (MiPLA), which has N-methyl and N-isopropyl groups.^[4][5][6]