HU-210

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HU-210
HU-210 structure.svg
Hu210 bns.png
Systematic (IUPAC) name
(6aR,10aR)-9-(hydroxymethyl)-6,6-dimethyl-3-(2-methyloctan-2-yl)-6H,6aH,7H,10H,10aH-benzo[c]isochromen-1-ol
Legal status
Legal status
Identifiers
CAS Number 112830-95-2 YesY
PubChem CID 9821569
IUPHAR/BPS 731
ChemSpider 7997318 YesY
UNII 191042422P
ChEMBL CHEMBL307696 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.

Effects and research[edit]

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[edit]

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]

HU-210 synthesis

Recreational use[edit]

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[edit]

HU-210 is not scheduled by the United Nations' Convention on Psychotropic Substances.[13]

New Zealand[edit]

HU-210 is banned in New Zealand as of 8 May 2014.[14]

United States[edit]

HU-210 is not listed in the list of scheduled controlled substances in the USA.[15] It is therefore not scheduled at the federal level in the United States, but it is possible that HU-210 could legally be considered an analog of Delta-8-THC and sales or possession could potentially be prosecuted under the Federal Analogue Act.[16] A brief profile of HU-210 written and published by the Drug Enforcement Administration (DEA) in 2009 (but subsequently removed from the DEA's website several years later) stated that HU-210 is a Schedule I controlled substance under the Controlled Substances Act due to being similar to Delta-8-THC which is one of the substances controlled in Schedule I as "Tetrahydrocannabinols."[17] This indicates that the DEA might legally consider HU-210 to be an analogue of Delta-8-THC for the purposes of applying the Federal Analog Act to those that handle HU-210. An elucidation of the rational for the DEA's claim was not presented, no references were cited, and the claim was eventually removed from the DEA's website. A version of the document (updated in 2013), now in PDF form, exists on the DEA Office of Diversion Control's website.[18] It claims, with the same lack of detailed explanation or citation, that:

Florida[edit]

HU-210 is a Schedule I controlled substance, categorized as a hallucinogen, making it illegal to buy, sell, or possess in the state of Florida without a license.[19]

Other HU Cannabinoids[edit]

See also[edit]

References[edit]

  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 (Mar 1989). "Stereochemical effects of 11-OH-Δ8-THC-dimethylheptyl in mice and dogs". Pharmacology, Biochemistry, and Behavior. 32 (3): 661–666. doi:10.1016/0091-3057(89)90014-2. 
  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 Medicinal 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 1253627free to read. 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. ^ Convention on Psychotropic Substances, 1971
  14. ^ https://www.drugfoundation.org.nz/synthetic-cannabinoids/what-they-are
  15. ^ §1308.11 Schedule I.
  16. ^ Erowid Analog Law Vault : Federal Controlled Substance Analogue Act Summary
  17. ^ "Spice Cannabinoid - HU-210". 
  18. ^ HU-210 [(6aR,10aR)-9-(hydroxymethyl)-6,6-dimethyl-3-(2-methyloctan-2-yl)-6a,7,10,10a-tetrahydrobenzo[c chromen-1-ol)] [Purported Ingredient of “Spice”]] (PDF). DEA Office of Diversion Control. Web. January 2013.
  19. ^ Florida Statutes - Chapter 893 - DRUG ABUSE PREVENTION AND CONTROL

External links[edit]