Jump to content

HU-210

From Wikipedia, the free encyclopedia

This is an old revision of this page, as edited by 98.212.150.175 (talk) at 07:53, 26 April 2011 (→See also). The present address (URL) is a permanent link to this revision, which may differ significantly from the current revision.

HU-210
Clinical data
Other names1,1-Dimethylheptyl- 11-hydroxy- tetrahydrocannabinol
Legal status
Legal status
  • Schedule I Controlled Substance in the USA [1][2]
Identifiers
  • (6aR,10aR)- 9-(Hydroxymethyl)- 6,6-dimethyl- 3-(2-methyloctan-2-yl)- 6a,7,10,10a-tetrahydrobenzo [c]chromen- 1-ol
CAS Number
PubChem CID
IUPHAR/BPS
ChemSpider
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC25H38O3
Molar mass386.567 g/mol g·mol−1
3D model (JSmol)
  • CC(C)(CCCCCC)c2cc1OC(C)(C)[C@H]3CC\C(=C/[C@@H]3c1c(O)c2)CO
  • InChI=1S/C25H38O3/c1-6-7-8-9-12-24(2,3)18-14-21(27)23-19-13-17(16-26)10-11-20(19)25(4,5)28-22(23)15-18/h13-15,19-20,26-27H,6-12,16H2,1-5H3/t19-,20-/m0/s1 checkY
  • Key:UEXRUIOOOVZHFZ-PMACEKPBSA-N checkY
 ☒NcheckY (what is this?)  (verify)

HU-210 is a synthetic cannabinoid that was first synthesized in 1988 from (1R,5S)-Myrtenol[3] by the group led by Professor Raphael Mechoulam at the Hebrew University.[4][5][6] HU-210 is 100 to 800 times more potent than natural THC from cannabis and has an extended duration of action.[7] 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 acts as an NMDA antagonist having neuroprotective effects.[8][9]

Per a 2005 article in the Journal of Clinical Investigation, HU-210 promotes proliferation, but not differentiation, of cultured embryonic hippocampal NS/PCs likely via a sequential activation of CB1 receptors, G(i/o) proteins, and ERK signaling. It was also indicated by this increased neural growth to entail antianxiety and antidepressant effects.[10]

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. Additionally, cannabinoids completely abolish neurotoxicity related to microglia activation in rat models.[11]

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

Recreational use

According to the U.S. Customs and Border Protection, HU-210 was discovered in Spice Gold products seized at the US border in January 2009. Over 100 pounds of Spice products were seized based on this finding,.[12] HU-210 was also detected in three Spice products in the UK, as reported in June 2009.[13]

United States

The US Drug Enforcement Administration announced on 24 November 2010 that it would use its emergency scheduling authority to ban HU-210 (among other synthetic cannabinoids) for one year while further studies are conducted. HU-210 would be placed under Schedule I status of the Controlled Substances Act after no fewer than 30 days from the date of the announcement. As of 24 December 2010, there has been no official announcement from the DEA that would classify HU-210 as a Schedule I substance [1]

To view states affected, see JWH-018. To view national schedule, see: List of Schedule I drugs (US), [1]

See also

References

  1. ^ a b http://www.deadiversion.usdoj.gov/drugs_concern/spice/spice_hu210.htm
  2. ^ http://www.deadiversion.usdoj.gov/schedules/orangebook/c_cs_alpha.pdf
  3. ^ 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.
  4. ^ Attention: This template ({{cite pmid}}) is deprecated. To cite the publication identified by PMID 3416993, please use {{cite journal}} with |pmid=3416993 instead.
  5. ^ 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.
  6. ^ Attention: This template ({{cite pmid}}) is deprecated. To cite the publication identified by PMID 2550611, please use {{cite journal}} with |pmid=2550611 instead.
  7. ^ Attention: This template ({{cite pmid}}) is deprecated. To cite the publication identified by PMID 1317925, please use {{cite journal}} with |pmid=1317925 instead.
  8. ^ Attention: This template ({{cite doi}}) is deprecated. To cite the publication identified by doi:10.1016/0028-3908(90)90056-W, please use {{cite journal}} (if it was published in a bona fide academic journal, otherwise {{cite report}} with |doi=10.1016/0028-3908(90)90056-W instead.
  9. ^ Darlington CL (2003). "Dexanabinol: a novel cannabinoid with neuroprotective properties". IDrugs : the Investigational Drugs Journal. 6 (10): 976–9. PMID 14534855. {{cite journal}}: Unknown parameter |month= ignored (help)
  10. ^ Attention: This template ({{cite pmid}}) is deprecated. To cite the publication identified by PMID 16224541, please use {{cite journal}} with |pmid=16224541 instead.
  11. ^ Attention: This template ({{cite pmid}}) is deprecated. To cite the publication identified by PMID 15728830, please use {{cite journal}} with |pmid=15728830 instead.
  12. ^ "Lab Results Confirm CBP in Ohio Discover Synthetic Narcotics in Incense Packets - CBP.gov".
  13. ^ "EMCDDA Action on new drugs briefing paper: Understanding the 'Spice' phenomenon" (PDF).
Retrieved from "https://en.wikipedia.org/enwiki/w/index.php?title=HU-210&oldid=425973907"