HU-210

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HU-210
200px
Systematic (IUPAC) name
(6aR,10aR)- 9-(Hydroxymethyl)- 6,6-dimethyl- 3-(2-methyloctan-2-yl)- 6a,7,10,10a-tetrahydrobenzo [c]chromen- 1-ol
Legal status
Legal status
  • Schedule I Controlled Substance in the USA [1] [2]
Identifiers
CAS Number 112830-95-2
PubChem CID 9821569
IUPHAR/BPS 731
Synonyms 1,1-Dimethylheptyl- 11-hydroxy- tetrahydrocannabinol
Chemical data
Formula C25H38O3
Molar mass 386.567 g/mol[[Script error: No such module "String".]]
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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.

Illicit 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].

Legal status

United States

HU-210 is currently a schedule I controlled substance under the Controlled Substances Act. [1]

See also

References

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External links


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  1. ↑ 1.0 1.1 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. ↑ Mechoulam, R; Feigenbaum, JJ; Lander, N; Segal, M; Järbe, TU; Hiltunen, AJ; Consroe, P (1988). "Enantiomeric cannabinoids: stereospecificity of psychotropic activity". Experientia. 44 (9): 762–4. doi:10.1007/BF01959156. PMID 3416993.  edit
  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. ↑ Järbe, TU; Hiltunen, AJ; 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): 1000–5. PMID 2550611.  edit
  7. ↑ Devane, WA; Breuer, A; Sheskin, T; Järbe, TU; Eisen, MS; Mechoulam, R (1992). "A novel probe for the cannabinoid receptor". Journal of medicinal chemistry. 35 (11): 2065–9. doi:10.1021/jm00089a018. PMID 1317925.  edit
  8. ↑ 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. doi:10.1016/0028-3908(90)90056-W. PMID 2158635.  edit
  9. ↑ Lua error in package.lua at line 80: module 'Module:Citation/CS1/Suggestions' not found.
  10. ↑ Jiang, W.; Zhang, Y.; Xiao, L.; Van Cleemput, J.; Ji, S.; Bai, G.; Zhang, X. (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 Freely accessible. PMID 16224541.  edit
  11. ↑ Ramírez, B.; Blázquez, C.; Gómez Del Pulgar, T.; Guzmán, M.; De Ceballos, M. (2005). "Prevention of Alzheimer's disease pathology by cannabinoids: neuroprotection mediated by blockade of microglial activation". The Journal of neuroscience : the official journal of the Society for Neuroscience. 25 (8): 1904–1913. doi:10.1523/JNEUROSCI.4540-04.2005. PMID 15728830.  More than one of |author2= and |last2= specified (help); More than one of |author3= and |last3= specified (help); More than one of |author4= and |last4= specified (help); More than one of |author5= and |last5= specified (help) edit
  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). 
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