Hexahydrocannabinol [HHC]

Hexahydrocannabinol (HHC) is a hydrogenated derivative of THC, presenting psychoactive properties. Initially reported by Roger Adams in 1940, HHC can be naturally found in trace amounts in Cannabis sativa or synthesized from cannabis extracts. It offers effects akin to THC and has gained popularity in North America and Europe. HHC’s synthesis methods and bioactivity have been explored, revealing its binding to CB1 receptors with less affinity compared to THC.

Chemistry and Synthesis:

• Synthesized (+)-HHC and (-)-HHC from citronellal and olivetol
• Elucidated HHC and related hydrogenated cannabinoid epimers using NMR spectroscopic techniques
• Isolated diastereomers using LC-MS and SCFC
• Discovered HHC in lipid extract from Cannabis sativa seeds
• HHC typically made from CBD with no double bonds in the cyclohexyl ring

Structural Analogues and Binding:

• Demonstrated binding of HHC analogs to CB receptor in animals
• 9β-HHC enantiomer more active than 9α-HHC
• HHC binds to CB receptor with weaker affinity than THC
• Found naturally occurring analogs in Cannabis
• HHC found as degradation byproduct of THC

Metabolism and Metabolites:

• D9-THC metabolizes into 11-Hydroxy-THC and alpha,10 alpha-epoxy-hexahydrocannabinol
• Cannabidiol metabolizes into 9α-hydroxy-HHC and 8-hydroxy-iso-HHC
• Methoxy or ethoxy analogs can be formed in the presence of alcohol
• Differentiate HHC from related compounds
• Various metabolites of THC and CBD

Legality and Regulations:

• Ban of HHC and derivatives in France, UK, and several European countries
• Ban of HHC in Austria, Sweden, Italy, Lithuania, and Slovenia
• Recommendation to add HHC to Novel Psychoactive Substances Act in Germany
• Pending enactment of HHC ban in Germany
• Various legal actions taken in different countries

References, Publications, and Government Sources:

• Studies on the synthesis and biological effects of HHC
• Reports on metabolite profiles and identification of cannabinoids
• Patents related to hydrogenation of cannabis oil
• Research on structure and isomerization of cannabinoids
• Reviews and analyses of HHC and related substances
• Citations from Pharmaceutical Sciences Journals, Research Studies, Legal Regulations, Publication Citations, and Government Websites

Hexahydrocannabinol Data Sources