Research ololuiqui entourage-effect under basic aqueous conditions

[braindead]

"The epimerization you are describing with ololiuqui (and others) is a highly specific chemical reaction that only affects a certain class of the plant's alkaloids. This basic environment triggers epimerization at the C-8 position of the ergoline ring, but it requires a specific structural vulnerability to work. This makes the C-8 proton relatively acidic. The alkaline water easily removes this proton, creating a resonance-stabilized enolate intermediate. When the molecule reprotonates, it can do so from either face, creating an equilibrium between the (8R)-epimer (e.g., ergine) and the (8S)-epimer (e.g., isoergine). Instead of a carboxamide group at C-8, lysergol has a hydroxymethyl group. It lacks the electron-withdrawing carbonyl group and cannot form an enolate intermediate. The C-8 proton in lysergol is simply not acidic enough to be stripped away by a mild base. Therefore, the traditional ash preparation is not harsh enough to force lysergol to epimerize into isolysergol; it remains entirely stable."

 

[Transform]

"The epimerization you are describing with ololiuqui (and others) is a highly specific chemical reaction that only affects a certain class of the plant's alkaloids. This basic environment triggers epimerization at the C-8 position of the ergoline ring, but it requires a specific structural vulnerability to work. This makes the C-8 proton relatively acidic. The alkaline water easily removes this proton, creating a resonance-stabilized enolate intermediate. When the molecule reprotonates, it can do so from either face, creating an equilibrium between the (8R)-epimer (e.g., ergine) and the (8S)-epimer (e.g., isoergine). Instead of a carboxamide group at C-8, lysergol has a hydroxymethyl group. It lacks the electron-withdrawing carbonyl group and cannot form an enolate intermediate. The C-8 proton in lysergol is simply not acidic enough to be stripped away by a mild base. Therefore, the traditional ash preparation is not harsh enough to force lysergol to epimerize into isolysergol; it remains entirely stable."

An attribution would be helpful here. What's the context of this quote? It's talking about structural correlates of susceptibility to epimerisation, not specifically directly about 'entourage effect', which is a downstream consequence of a given mixed alkaloidal profile.