HU-210

HU-210
Systematic (IUPAC) name
(6aR,10aR)- 9-(Hydroxymethyl)- 6,6-dimethyl- 3-(2-methyloctan-2-yl)- 6a,7,10,10a-tetrahydrobenzo [c]chromen- 1-ol
Clinical data
Legal status
Identifiers
CAS Number 112830-95-2 YesY
PubChem CID 9821569
IUPHAR/BPS 731
ChemSpider 21106322 YesY
ChEMBL CHEMBL70625 N
Synonyms 1,1-Dimethylheptyl- 11-hydroxy- tetrahydrocannabinol
Chemical data
Formula C25H38O3
Molar mass 386.567 g/mol
 NYesY (what is this?)  (verify)

HU-210 is a synthetic cannabinoid that was first synthesized in 1988 from (1R,5S)-myrtenol[1] by a group led by Professor Raphael Mechoulam at the Hebrew University.[2][3][4] HU-210 is 100 to 800 times more potent than natural THC from cannabis and has an extended duration of action.[5] HU-210 is the (–)-1,1-dimethylheptyl analog of 11-hydroxy- Δ8- tetrahydrocannabinol; in some references it is called 1,1-dimethylheptyl- 11-hydroxytetrahydrocannabinol. The abbreviation "HU" stands for Hebrew University.

The (+) enantiomer of HU-210 has almost all of the cannabinoid activity, with the (−) enantiomer HU-211 being inactive as a cannabinoid but instead acting as an NMDA antagonist having neuroprotective effects.[6][7]

HU-210 promotes proliferation, but not differentiation, of cultured embryonic hippocampal neural stem and progenitor cells likely via a sequential activation of CB1 receptors, Gi/o proteins, and ERK signaling. It was also indicated by this increased neural growth to entail antianxiety and antidepressant effects.[8]

HU-210, alongside other synthetic cannabinoids like WIN 55,212-2 and JWH-133, is implicated in preventing the inflammation caused by amyloid beta proteins involved in Alzheimer's disease, in addition to preventing cognitive impairment and loss of neuronal markers. This anti-inflammatory action is induced through the activation of cannabinoid receptors, which prevents microglial activation that elicits the inflammation. In addition, cannabinoids completely abolish neurotoxicity related to microglia activation in rat models.[9]

HU-210 is a potent analgesic with many of the same effects as natural THC.

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).[10]

Recreational use

According to the U.S. Customs and Border Protection, HU-210 was discovered in Spice Gold incense products seized at the US border in January 2009. Over 100 pounds of Spice products were seized based on this finding.[11] HU-210 was also detected in three Spice products in the UK, as reported in June 2009.[12]

Legal status

United States

HU-210 is a schedule I controlled substance under the Controlled Substances Act.[13]

To view national schedule, see: List of Schedule I drugs (US),

New Zealand

Banned in New Zealand as of 8 May 2014.[14]

Other HU Cannabinoids

See also

References

  1. ↑ Mechoulam, R., Lander, N., Breuer, A., Zahalka, J. Synthesis of the Individual, Pharmacologically Distinct, Enantiomers of a Tetrahydrocannabinol Derivative. Tetrahedron: Asymmetry. 1990. Vol 1, No 5. pp 315-318.
  2. ↑ Mechoulam, R.; et al. (1988). "Enantiomeric cannabinoids: stereospecificity of psychotropic activity". Experientia 44 (9): 762–764. doi:10.1007/BF01959156. PMID 3416993.
  3. ↑ Little PJ, Compton DR, Mechoulam R, Martin BR. Stereochemical effects of 11-OH-Δ8-THC-dimethylheptyl in mice and dogs. Pharmacology, Biochemistry, and Behavior. 1989 Mar;32(3):661-666.
  4. ↑ Järbe, T.; Hiltunen, A.; Mechoulam, R. (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 250 (3): 1000–1005. PMID 2550611.
  5. ↑ Devane, W. A.; et al. (1992). "A novel probe for the cannabinoid receptor". Journal of Medical Chemistry 35 (11): 2065–2069. doi:10.1021/jm00089a018. PMID 1317925.
  6. ↑ Howlett, A.; Champion, T.; Wilken, G.; Mechoulam, R. (1990). "Stereochemical effects of 11-OH-Δ8-tetrahydrocannabinol-dimethylheptyl to inhibit adenylate cyclase and bind to the cannabinoid receptor". Neuropharmacology 29 (2): 161–5. doi:10.1016/0028-3908(90)90056-W. PMID 2158635.
  7. ↑ Darlington CL (October 2003). "Dexanabinol: a novel cannabinoid with neuroprotective properties". IDrugs : the Investigational Drugs Journal 6 (10): 976–9. PMID 14534855.
  8. ↑ Jiang, W.; et al. (2005). "Cannabinoids promote embryonic and adult hippocampus neurogenesis and produce anxiolytic- and antidepressant-like effects". The Journal of Clinical Investigation 115 (11): 3104–3116. doi:10.1172/JCI25509. PMC 1253627. PMID 16224541.
  9. ↑ Ramírez Bg, E. A. ; Blázquez, C.; Gómez Del Pulgar, T.; Guzmán, M.; De Ceballos, M. L. (2005). "Prevention of Alzheimer's disease pathology by cannabinoids: neuroprotection mediated by blockade of microglial activation". Journal of Neuroscience 25 (8): 1904–1913. doi:10.1523/JNEUROSCI.4540-04.2005. PMID 15728830.
  10. ↑ R. Mechoulam, N. Lander, A. Breuer, J. Zahalka: In Synthesis of the Individual, Pharmacologically Distinct, Enantiomers of a Tetrahydrocannabinol Derivative. Tetrahedron: Asymmetry 1990, 5, 315-318.
  11. ↑ "Lab Results Confirm CBP in Ohio Discover Synthetic Narcotics in Incense Packets - CBP.gov".
  12. ↑ "EMCDDA Action on new drugs briefing paper: Understanding the ‘Spice’ phenomenon" (PDF).
  13. ↑ "Spice Cannabinoid - HU-210".
  14. ↑ https://www.drugfoundation.org.nz/synthetic-cannabinoids/what-they-are

External links

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