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Evidence of global relevance

Synthetic Pathway of Nonpsychoactive Cannabidiol from Psychoactive Tetrahydrocannabinol: A DFT Guide

A DFT study proposed a two-step conversion of Δ9-THC to CBD using BCl3 and a selective base, also examining Δ8-THC and CBN. Although overall reaction free energies were negative, the predicted rate-determining barriers were 49.4-54.1 kcal/mol—very high values—so experimental feasibility under mild conditions and scalability remain unproven.

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Key findings

  • TS4-5 was predicted to be rate determining, with ΔG‡ values of 49.4, 50.3, and 54.1 kcal/mol for Δ9-THC, Δ8-THC, and CBN. Overall ΔGrxn ranged from -33.9 to -32.9 kcal/mol, indicating thermodynamic favourability, but the high barriers alone do not support rapid conversion under mild conditions.
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Why this matters globally

Selective cannabinoid transformation matters to medicinal chemistry and manufacturing control. Computation can narrow experimental space and identify bottlenecks, but safety, regulation, residues, selectivity, and process economics require separate evaluation.

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Thai researcher contribution

The Center of Excellence in Computational Chemistry at Chulalongkorn University and the Department of Chemistry at Kasetsart University jointly developed the molecular mechanism model.

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Limitations to consider

This is computational work without synthesis, conversion, yield, selectivity, by-product, solvent, or scale-up measurements. Results depend on the theoretical level and model assumptions. Nonpsychoactive does not mean safe or therapeutically effective.

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Verify the original sources

The Journal of Organic ChemistryRead the original article

DOI: 10.1021/acs.joc.6c00898

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