View source for HU-210

{{Drugbox|
|IUPAC_name = (6a''R'',10a''R'')- 9-(Hydroxymethyl)- 6,6-dimethyl- 3-(2-methyloctan-2-yl)- 6a,7,10,10a-tetrahydrobenzo [c]chromen- 1-ol
| synonyms= 1,1-Dimethylheptyl- 11-hydroxy- tetrahydrocannabinol 
| image = HU-210_structure.png
| width= 200px
| CAS_number= 112830-95-2 
| ATC_prefix=
| ATC_suffix=
| PubChem=  9821569 
| IUPHAR_ligand = 731
| DrugBank=
| C=25 | H=38 | O=3
| molecular_weight = 386.567 g/mol
| bioavailability=
| metabolism = 
| elimination_half-life= 
| excretion = 
| pregnancy_category =
| legal_status = Schedule I Controlled Substance in the USA <ref name="usdoj_spice">http://www.deadiversion.usdoj.gov/drugs_concern/spice/spice_hu210.htm</ref> <ref>http://www.deadiversion.usdoj.gov/schedules/orangebook/c_cs_alpha.pdf</ref>
| routes_of_administration= 
}}

'''HU-210''' is a [[Chemical synthesis|synthetic]] [[cannabinoid]] that was first synthesized in [[1988]] from (1R,5S)-Myrtenol<ref>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.</ref> by the group led by Professor [[Raphael Mechoulam]] at the [[Hebrew University]].<ref>{{Cite pmid|3416993}}</ref><ref>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.</ref><ref>{{Cite pmid|2550611}}</ref> HU-210 is 100 to 800 times more potent than natural [[THC]] from [[cannabis]] and has an extended duration of action.<ref name="pmid1317925">{{Cite pmid|1317925}}</ref> HU-210 is the (–)-1,1-dimethylheptyl analog of 11-hydroxy- Δ<sup>8</sup>-  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.<ref>{{cite doi|10.1016/0028-3908(90)90056-W}}</ref><ref name="pmid14534855">{{cite journal |author=Darlington CL |title=Dexanabinol: a novel cannabinoid with neuroprotective properties |journal=IDrugs : the Investigational Drugs Journal |volume=6 |issue=10 |pages=976–9 |year=2003 |month=October |pmid=14534855 |doi= |url=}}</ref>

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.<ref name="pmid16224541">{{Cite pmid|16224541}}</ref>

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 receptor]]s which prevents [[microglia]]l activation that elicits the inflammation. Additionally, cannabinoids completely abolish neurotoxicity related to microglia activation in rat models.<ref name="pmid15728830">{{Cite pmid|15728830}}</ref> 

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

==Illicit use==
According to the [[U.S. Customs and Border Protection]], HU-210 was discovered in [[Spice (drug)|Spice Gold]] products seized at the US border in January 2009. Over 100 pounds of Spice products were seized based on this finding,<ref name="urlLab Results Confirm CBP in Ohio Discover Synthetic Narcotics in Incense Packets - CBP.gov">{{cite web |url=http://www.cbp.gov/xp/cgov/newsroom/news_releases/01142009_3.xml |title=Lab Results Confirm CBP in Ohio Discover Synthetic Narcotics in Incense Packets - CBP.gov |format= |work= |accessdate=}}</ref>. HU-210 was also detected in three Spice products in the UK, as reported in June 2009.<ref>{{cite web|url=http://www.emcdda.europa.eu/attachements.cfm/att_80086_EN_EMCDDA_Understanding%20the%20‘Spice’%20phenomenon_1Update%2020090514.pdf|title=EMCDDA Action on new drugs briefing paper: Understanding the ‘Spice’ phenomenon}}</ref>.

==Legal status==

===United States===
HU-210 is currently a schedule I controlled substance under the [[Controlled Substances Act]]. <ref name="usdoj_spice" />

== See also ==
* [[Spice (drug)]]
* [[JWH-018]]
* [[CP 47,497]]

==References==
{{Reflist}}
== External links ==
* [http://dx.doi.org/10.1038/news051010-12 Comment in Nature on the article about neurogenesis.]

{{Cannabinoids}}

[[Category:Cannabinoids]]
[[Category:Benzochromenes]]
[[Category:Alcohols]]
[[Category:Phenols]]


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