Methiodide

In organic chemistry, a methiodide is a chemical derivative produced by the reaction of a compound with methyl iodide. Methiodides are often formed through the methylation of tertiary amines:

R3N + CH3I → (CH3)R3N+I−

Whereas the parent amines are hydrophobic and often oily, methiodides, being salts, are somewhat hydrophilic and exhibit high melting points. Methiodides exhibit altered pharmacological properties as well.

Examples include:

  • Cocaine methiodide, a charged cocaine analog which cannot pass the blood brain barrier and enter the brain[1]
  • Bicuculline methiodide, a water-soluble form of bicuculline

Tertiary phosphines and phosphite esters also form methiodides.[2]

References
  1. Hill ER, Tian J, Tilley MR, Zhu MX, Gu HH (2009). Manzoni OJ (ed.). "Potencies of Cocaine Methiodide on Major Cocaine Targets in Mice". PLOS ONE. 4 (10): e7578. Bibcode:2009PLoSO...4.7578H. doi:10.1371/journal.pone.0007578. PMC 2762027. PMID 19855831.
  2. H. N. Rydon (1971). "Alkyl Iodides: Neopentyl Iodide and Iodocyclohexane". Organic Syntheses. 51: 44. doi:10.15227/orgsyn.051.0044.


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