Psilocin Salt Forms for Crystallinity, Stability, and Solubility
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Solution Overview
Problem
Psilocin's poor crystallinity, limited bulk purity upon crystallization, susceptibility to auto-catalyzed oxidation, and low water solubility hinder its therapeutic applications due to physical properties.
Innovation Solution
Development of pharmaceutically acceptable salts such as 1:1 benzoate, 1:1 tartrate, 2:1 succinate, and 1,5-naphthalenedisulfonic acid salts of psilocin, along with specific crystal forms, to enhance stability and solubility.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Reliability
If psilocin is used in its free base form, then it can be handled and stored, but it exhibits poor crystallinity, limited bulk purity upon crystallization, susceptibility to auto-catalyzed oxidation, and low water solubility
Solution Approach 1:
The patent applies parameter changes by converting psilocin from its free base form to salt forms through chemical modification. Specifically, psilocin is converted to salts such as psilocin sulfate, psilocin hydrochloride, and psilocin phosphate by reacting with appropriate acids. This chemical transformation changes the physical and chemical parameters of the compound, resulting in improved crystallinity, enhanced bulk purity upon crystallization, increased water solubility, and reduced susceptibility to auto-catalyzed oxidation. The salt forms maintain the therapeutic activity of psilocin while resolving the manufacturing and stability issues of the free base form.
2Manufacturing precision
If psilocin is crystallized to improve purity, then bulk purity is limited, but crystallization process is complex due to poor crystallinity
Solution Approach 1:
The patent resolves the crystallization complexity by changing the chemical form of psilocin to salt forms. The salt forms exhibit superior crystallinity compared to the free base form, enabling straightforward crystallization processes. For example, psilocin sulfate, psilocin hydrochloride, and psilocin phosphate form well-defined crystals that can be easily purified through standard crystallization techniques. This parameter change from free base to salt form transforms a complex, low-yield crystallization process into a simple, high-yield purification process, achieving both high bulk purity and process simplicity.
3Duration of action of stationary object
If psilocin is stored for prolonged periods, then it can be handled, but it is susceptible to auto-catalyzed oxidation
Solution Approach 1:
The patent addresses oxidation susceptibility by changing psilocin to salt forms with enhanced oxidative stability. The salt forms (sulfate, hydrochloride, phosphate) exhibit reduced susceptibility to auto-catalyzed oxidation compared to the free base form. This parameter change in chemical structure protects the indole ring and tryptamine backbone from oxidation during prolonged storage, extending shelf life and maintaining therapeutic potency over time. The improved oxidative stability allows for longer storage durations without significant degradation.
4Reliability
If psilocin is administered for therapeutic effects, then it shows promise for neurological and psychiatric conditions, but low water solubility limits its formulation and delivery
Solution Approach 1:
The patent resolves the solubility limitation by transforming psilocin into salt forms with enhanced aqueous solubility. The salt forms including psilocin sulfate, psilocin hydrochloride, and psilocin phosphate exhibit significantly improved water solubility compared to the free base form. This parameter change enables effective pharmaceutical formulation and delivery, allowing psilocin to be administered in aqueous solutions or suspensions. The improved solubility facilitates various routes of administration while maintaining therapeutic efficacy for neurological and psychiatric conditions.
Data Source
AI summary
The present invention composition features pharmaceutically acceptable salts of psilocin and compositions thereof. The pharmaceutically acceptable salts of psilocin may be used to treat a disease or condition, such as a neurological injury, an inflammatory condition, chronic pain, or a psychological condition, in a subject in need thereof.