Crystalline DMT Salt Forms for Solubility, Stability, and Melting Point

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Solution Overview

Problem

Existing DMT free base exhibits low melting point, low solubility in water, and fast degradation rate, making it challenging for effective drug formulation and bioavailability.

Innovation Solution

Development of novel DMT salt forms such as fumarate Form A, succinate Form A, malate Form A, oxalate Form A, and sulfate Form A, which offer improved melting point, aqueous solubility, and reduced hygroscopicity compared to DMT free base.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Stability of the object's composition

If DMT free base is used, then the compound maintains its basic structure and activity, but it exhibits low melting point, low aqueous solubility, and fast degradation rate

Engineering Contradiction:

Improvedegradation rateVSAvoidformulation difficulty

Core Design Contradiction:

Stability of the object's compositionVSEase of manufacture

Solution Approach 1:

The patent applies parameter changes by converting DMT from free base form to various salt forms (hydrochloride, sulfate, succinate, malate, fumarate, oxalate). This chemical parameter change fundamentally alters the physicochemical properties: the salt forms exhibit higher melting points, significantly improved aqueous solubility, and enhanced stability with reduced degradation rates, while maintaining the core DMT structure and pharmacological activity

Inventive Principle:

Principle #35Parameter changes

Solution Approach 2:

The patent creates composite material systems by forming salts of DMT with various counterions (Cl-, SO4 2-, succinate 2-, malate 2-, fumarate 2-, oxalate 2-). These composite salt forms combine the active DMT molecule with stabilizing counterions, resulting in materials that maintain therapeutic activity while possessing improved formulation characteristics including better solubility, stability, and handling properties

Inventive Principle:

Principle #40Composite materials

2Quantity of substance

If DMT free base is used, then the compound structure is simple, but it has extremely low solubility in water

Engineering Contradiction:

Improveaqueous solubilityVSAvoidsalt form complexity

Core Design Contradiction:

Quantity of substanceVSDevice complexity

Solution Approach 1:

The patent improves aqueous solubility by changing the chemical parameter of DMT from neutral free base to ionic salt forms. The salt forms (hydrochloride, sulfate, succinate, malate, fumarate, oxalate) possess ionizable groups that dramatically enhance water solubility, enabling effective formulation concentrations while the structural complexity remains manageable through systematic salt formation

Inventive Principle:

Principle #35Parameter changes

3Temperature

If DMT free base is used, then the compound is easy to isolate as clear or white crystals, but it has low melting point between 44.6° C. and 46.8° C.

Engineering Contradiction:

Improvemelting pointVSAvoidstorage requirements

Core Design Contradiction:

TemperatureVSEase of manufacture

Solution Approach 1:

The patent raises the melting point parameter by converting DMT free base (melting point 44.6-46.8° C.) to various salt forms. The salt forms exhibit significantly higher melting points due to the ionic lattice structure, which improves thermal stability and reduces storage requirements, eliminating the need for cold chain storage while maintaining compound integrity

Inventive Principle:

Principle #35Parameter changes

Data Source

PatentUS12378194B2N, n-dimethyltryptamine salts and crystalline salt forms

Publication Date: 2025.08.05 ATAI THERAPEUTICS INC

AI summary

A N,N-dimethyltryptamine (DMT) succinate crystalline form.