Synthesis and Pyrolysis of UR-144: A Detailed Guide


UR-144, a synthetic cannabinoid with various street names like TMCP-018, KM-X1, MN-001, and YX-17, is a compound of interest due to its use in 'legal high' products. However, its structural feature, a cyclopropane ring, poses thermal instability concerns, especially when consumed by smoking. This article delves into the synthesis of UR-144, its thermal behavior during pyrolysis, and its potential transformations.

UR-144 Synthesis: A Closer Look

UR-144 is a synthetic cannabinoid identified in a range of commercial products, including herbal, resin, and powder substances. This compound has several analogs, one of which is a novel hydrated derivative. To understand its synthesis better, we explore its structural aspects.


The Cyclopropane Conundrum

The cyclopropane moiety in UR-144 is particularly susceptible to thermal isomerization. This instability becomes concerning as the temperatures at the tip of a burning cigarette can exceed 700 °C. At these high temperatures, various ring-opening reactions may occur in the cyclopropane moiety, leading to the formation of different compounds.

UR-144 Pyrolysis: Unveiling the Transformations

This article also focuses on the pyrolysis of UR-144, shedding light on the transformation process when subjected to heat, such as during smoking. It is crucial to understand these transformations, as they can significantly impact the compounds' pharmacological properties.

Discussion: The Mystery of Synthetic Cannabinoids

Synthetic cannabinoids, like UR-144, have emerged as a challenge in forensic toxicology and drug analysis. While they interact with cannabinoid receptors, their effects differ substantially from natural marijuana, suggesting unique toxicity mechanisms. Pyrolysis products, as explored in this article, may contribute to these distinct psychological effects.

Reported pyrolytic products of two synthetic cannabinoids.

UR-144 Unmasked: Structural Insights

UR-144, structurally similar to JWH-018, contains a cyclopropane ring that is considered thermally unstable. This instability raises concerns about its behavior during heating. The article discusses the main pyrolytic product of UR-144 and its implications.

The Main Pyrolytic Product

The main pyrolytic product of UR-144 is identified as 3,3,4-trimethyl-1-(1-pentyl-1H-indol-3-yl)pent-4-en-1-one. This compound's formation is attributed to the breaking of the cyclopropane ring, resulting in the creation of an isobutylene group. This transformation is a crucial aspect of UR-144's behavior when exposed to heat.

Proposed scheme of reactions for compounds related to UR-144.

Metabolism and Biomarkers

Understanding the metabolism of compounds like UR-144 is essential for drug screening. Metabolites of the main pyrolytic product, including mono-hydroxylation, di-hydroxylation, carboxylation, and dealkylation products, are identified as potential biomarkers for smoked UR-144.

Conclusion: UR-144 - Unveiling Its Mysteries

In conclusion, UR-144's thermal instability and its cyclopropane ring's vulnerability to transformation have been explored. These transformations, including pyrolysis and metabolite formation, contribute to the compound's unique properties and effects. Further research is needed to fully comprehend the pharmacological implications of these transformations and their individual roles as novel synthetic cannabinoids.

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    UR-144 synthesis from TMCP-indole (large scale). Video manual.
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