Synthesis of a psilocin hapten and a protein-hapten conjugate
Journal of Pharmacy and Pharmacology – September 01, 2002
Source: OpenAlex
Summary
A significant advance in drug analysis involves creating stable psilocin derivatives. Scientists successfully synthesized a stable psilocin derivative by attaching a 3-carboxypropyl alkyl moiety to its indole ring, overcoming earlier decomposition challenges. This hapten was then conjugated to bovine serum albumin, with mass spectrometry confirming 4-5 psilocin molecules per protein. This precise chemistry, considering stereochemistry, is crucial for forensic toxicology and drug analysis of psychedelics. Such work underpins broader drug studies, including those on nicotinic acetylcholine receptors, and utilizes techniques like chromatography and the indole test.
Abstract
Abstract Derivatives of psilocin with ω-functionalized alkyl spacers in position 1 of the indole ring were synthesized as haptens for use in a radioimmunoassay. Whereas the psilocin analogues with a 3-aminopropyl and a 4-aminobutyl moiety at the indole nitrogen decomposed during synthesis, the analogous 3-carboxypropyl psilocin derivative proved to be stable. This compound was coupled to bovine serum albumin (BSA) using the N-hydroxysuccinimide ester-mediated conjugation. The protein–hapten conjugate was characterized by matrix-assisted laser desorption ionization mass spectrometry. The mass spectrometry data indicated an average incorporation ratio of 4–5 molecules of psilocin hapten per molecule of BSA.