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HU-210

Synthetic cannabinoid

HU-210

Synthetic cannabinoid

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HU-210 is a synthetic cannabinoid that was first synthesized in 1988 from (1R,5S)-myrtenol by a group led by Raphael Mechoulam at the Hebrew University. HU-210 is 100 to 800 times more potent than natural THC from cannabis and has an extended duration of action. HU-210 has a binding affinity of 0.061 nM at CB1 receptors compared to 40.7 nM for Δ9-THC. The binding pose of HU-210 to the CB1 receptor is similar to other synthetic cannabinoids.

Effects and research

HU-210, the (–) enantiomer, is an ultrapotent cannabinoid, while its (+) enantiomer HU-211 is not a cannabinoid, but an NMDA antagonist with neuroprotective effects.

HU-210 has an oral LD50 of 5,000 mg/kg in rats and 14,200 mg/kg in rabbits, and an LDLO (lowest lethal dose) of 143 mg/kg in humans. This is more toxic than Δ8-THC; in monkeys and dogs, 9,000 mg/kg of Δ8-THC was nonlethal.

Chemistry

HU-210 is the enantiomer of HU-211 (dexanabinol). The original synthesis of HU-210 is based on an acid-catalyzed condensation of (–)-Myrtenol and 1,1-Dimethylheptylresorcinol (3,5-Dihydroxy-1-(1,1-dimethylheptyl)benzol).

HU-210 synthesis

References

References

  1. (January 1990). "Synthesis of the individual, pharmacologically distinct, enantiomers of a tetrahydrocannabinol derivative". Tetrahedron: Asymmetry.
  2. (September 1988). "Enantiomeric cannabinoids: stereospecificity of psychotropic activity". Experientia.
  3. (March 1989). "Stereochemical effects of 11-OH-delta 8-THC-dimethylheptyl in mice and dogs". Pharmacology, Biochemistry, and Behavior.
  4. (September 1989). "Stereospecificity of the discriminative stimulus functions of the dimethylheptyl homologs of 11-hydroxy-delta 8-tetrahydrocannabinol in rats and pigeons". The Journal of Pharmacology and Experimental Therapeutics.
  5. (May 1992). "A novel probe for the cannabinoid receptor". Journal of Medicinal Chemistry.
  6. (August 2007). "Medicinal chemistry endeavors around the phytocannabinoids". Chemistry & Biodiversity.
  7. (2016). "The Structure-Function Relationships of Classical Cannabinoids: CB1/CB2 Modulation". Perspectives in Medicinal Chemistry.
  8. (2025). "Structural basis of THC analog activity at the Cannabinoid 1 receptor". Nature Communications.
  9. (February 1990). "Stereochemical effects of 11-OH-delta 8-tetrahydrocannabinol-dimethylheptyl to inhibit adenylate cyclase and bind to the cannabinoid receptor". Neuropharmacology.
  10. (October 2003). "Dexanabinol: a novel cannabinoid with neuroprotective properties". IDrugs.
  11. "HU-210". Cayman Chemical.
  12. (July 1973). "Comparison of acute oral toxicity of cannabinoids in rats, dogs and monkeys". Toxicology and Applied Pharmacology.
  13. "delta-8-Tetrahydrocannabinol". U.S. National Library of Medicine.
  14. "International Drug Control Conventions". United Nations Office on Drugs and Crime.
  15. "Synthetic cannabinoids: What they are". New Zealand Drug Foundation.
  16. "PART 1308 - Section 1308.11 Schedule I". Drug Enforcement Administration, U.S. Department of Justice.
  17. "Spice Cannabinoid - HU-210". Drug Enforcement Administration, U.S. Department of Justice.
  18. (January 2013). "HU-210". Drug Enforcement Administration, U.S. Department of Justice.
  19. (November 2024). "Lists of Scheduling Actions, Controlled Substances, and Regulated Chemicals". Drug and Chemical Evaluation Section, Diversion Control Division, Drug Enforcement Administration Division, U.S. Department of Justice.
  20. (March 2014). "Controlled substances, Schedule I, additional synthetic controlled substances and analogue substances included in, trafficking in controlled substance analogues, requisite weight increased, Secs. 13A-12-231, 20-2-23 am'd.". Alabama Senate Bill 333.
  21. "Chapter 893: Drug Abuse Prevention and Control". The Florida Legislature.
  22. (15 July 2017). "Code of Vermont Rules". Vermont Department of Health.
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