HU-210 explained

HU-210 is a synthetic cannabinoid that was first synthesized in 1988 from (1R,5S)-myrtenol[1] by a group led by 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 has a binding affinity of 0.061 nM at CB1 and 0.52 nM at CB2 in cloned human cannabinoid receptors[6] compared to delta-9-THC of 40.7 nM at CB1. [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.

Effects and research

HU-210, the (–) enantiomer of 11-OH-D8-THC-DMH, has almost all of the cannabinoid activity, while the (+) enantiomer, known as HU-211, is inactive as a cannabinoid and instead acts as an NMDA antagonist having neuroprotective effects.[8] [9]

HU-210 has an oral LD50 of 5,000 mg/kg in rats and 14,200 mg/kg in rabbits.[10] HU-210 has an LDLO (Lowest Lethal Dose amount) of 143 mg/kg in humans.[10] Delta-8-THC LD50 has not been confirmed. In a 1973 study monkeys and dogs given 9,000 mg/kg of delta-8-THC was nonlethal.[11] [12]

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).[1]

Legal status

HU-210 is not listed in the schedules set out by the United Nations' Single Convention on Narcotic Drugs from 1961 nor their Convention on Psychotropic Substances from 1971,[13] so the signatory countries to these international drug control treaties are not required by said treaties to control HU-210.

New Zealand

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

United States

HU-210 is not explicitly listed in the list of scheduled controlled substances in the USA.[15] A brief profile of HU-210 written and published by the Drug Enforcement Administration (DEA) in 2009, but removed in later years, stated that HU-210 is a Schedule I controlled substance under the Controlled Substances Act due to being similar to THC.[16] A version of the document (updated in 2013), now in PDF form, exists on the DEA Office of Diversion Control's website.[17] In that PDF, the DEA reasserts that HU-210 is a Schedule I substance. The DEA currently considers HU-210 a Schedule I controlled substance under the umbrella of ‘tetrahydrocannabinols’ under CSCN 7370.[18]

Alabama

HU-210 is a Schedule I controlled substance in Alabama.[19]

Florida

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.[20]

Vermont

Effective January 1, 2016, HU-210 is a regulated drug in Vermont designated as a "Hallucinogenic Drug."[21]

See also

Further reading

Notes and References

  1. Mechoulam R, Lander N, Zahalka J . Synthesis of the individual, pharmacologically distinct, enantiomers of a tetrahydrocannabinol derivative . Tetrahedron: Asymmetry . January 1990 . 1 . 5 . 315–318 . 10.1016/S0957-4166(00)86322-3 .
  2. Mechoulam R, Feigenbaum JJ, Lander N, Segal M, Järbe TU, Hiltunen AJ, Consroe P . Enantiomeric cannabinoids: stereospecificity of psychotropic activity . Experientia . 44 . 9 . 762–4 . September 1988 . 3416993 . 10.1007/BF01959156 . 19589995 .
  3. Little PJ, Compton DR, Mechoulam R, Martin BR . Stereochemical effects of 11-OH-delta 8-THC-dimethylheptyl in mice and dogs . Pharmacology, Biochemistry, and Behavior . 32 . 3 . 661–6 . March 1989 . 2544901 . 10.1016/0091-3057(89)90014-2 . 140209484 .
  4. Järbe TU, Hiltunen AJ, Mechoulam R . 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 . September 1989 . 2550611 .
  5. Devane WA, Breuer A, Sheskin T, Järbe TU, Eisen MS, Mechoulam R . A novel probe for the cannabinoid receptor . Journal of Medicinal Chemistry . 35 . 11 . 2065–9 . May 1992 . 1317925 . 10.1021/jm00089a018 .
  6. Stern E, Lambert DM . Medicinal chemistry endeavors around the phytocannabinoids . Chemistry & Biodiversity . 4 . 8 . 1707–1728 . August 2007 . 17712816 . 10.1002/cbdv.200790149 . 24920412 .
  7. Bow EW, Rimoldi JM . The Structure-Function Relationships of Classical Cannabinoids: CB1/CB2 Modulation . Perspectives in Medicinal Chemistry . 8 . 17–39 . 2016 . 27398024 . 4927043 . 10.4137/PMC.S32171 .
  8. Howlett AC, Champion TM, Wilken GH, Mechoulam R . Stereochemical effects of 11-OH-delta 8-tetrahydrocannabinol-dimethylheptyl to inhibit adenylate cyclase and bind to the cannabinoid receptor . Neuropharmacology . 29 . 2 . 161–5 . February 1990 . 2158635 . 10.1016/0028-3908(90)90056-w . 28602221 .
  9. Darlington CL . Dexanabinol: a novel cannabinoid with neuroprotective properties . IDrugs . 6 . 10 . 976–9 . October 2003 . 14534855 . 112453448 .
  10. Web site: HU-210 . Material Safety Data Sheet . Cayman Chemical .
  11. Thompson GR, Rosenkrantz H, Schaeppi UH, Braude MC . Comparison of acute oral toxicity of cannabinoids in rats, dogs and monkeys . Toxicology and Applied Pharmacology . 25 . 3 . 363–72 . July 1973 . 4199474 . 10.1016/0041-008X(73)90310-4 .
  12. Web site: delta-8-Tetrahydrocannabinol . ChemIDplus . U.S. National Library of Medicine .
  13. Web site: International Drug Control Conventions . United Nations Office on Drugs and Crime . 3 May 2018 . live. https://web.archive.org/web/20180112202649/https://www.unodc.org/unodc/en/commissions/CND/conventions.html . 12 January 2018.
  14. Web site: Synthetic cannabinoids: What they are . 2015-07-18 . dead . https://web.archive.org/web/20150921191334/http://www.drugfoundation.org.nz/synthetic-cannabinoids/what-they-are . 2015-09-21 . New Zealand Drug Foundation .
  15. Web site: PART 1308 - Section 1308.11 Schedule I . Office of Diversion Control . Drug Enforcement Administration, U.S. Department of Justice . 3 May 2018. live. https://web.archive.org/web/20090827043725/http://www.deadiversion.usdoj.gov/21cfr/cfr/1308/1308_11.htm . 27 August 2009.
  16. Web site: Spice Cannabinoid - HU-210. dead . https://web.archive.org/web/20120117131045/http://www.deadiversion.usdoj.gov/drugs_concern/spice/spice_hu210.htm. 2012-01-17 . Office of Diversion Control . Drug Enforcement Administration, U.S. Department of Justice .
  17. Web site: 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” . https://web.archive.org/web/20161228044049/https://www.deadiversion.usdoj.gov/drug_chem_info/spice/spice_hu210.pdf . 2016-12-28 . Office of Diversion Control . Drug Enforcement Administration, U.S. Department of Justice . January 2013 .
  18. https://www.deadiversion.usdoj.gov/schedules/orangebook/orangebook.pdf
  19. Web site: Controlled substances, Schedule I, additional synthetic controlled substances and analogue substances included in, trafficking in controlled substance analogues, requisite weight increased, Secs. 13A-12-231, 20-2-23 am'd. . Alabama Senate Bill 333 . March 2014 . 2 February 2017 . live . https://web.archive.org/web/20160304083946/https://legiscan.com/AL/text/SB333/2014 . 4 March 2016 .
  20. Web site: Chapter 893: Drug Abuse Prevention and Control . The 2020 Florida Statutes . The Florida Legislature . 3 May 2018. live. https://web.archive.org/web/20180314154145/http://www.leg.state.fl.us/Statutes/index.cfm?App_mode=Display_Statute&URL=0800-0899%2F0893%2F0893.html. 14 March 2018.
  21. Book: Code of Vermont Rules . Chapter 8 – Alcohol and Drug Abuse Subchapter 9: Regulated Drug Rule . Vermont Department of Health . 15 July 2017 . 3 May 2018 . http://www.healthvermont.gov/sites/default/files/documents/2017/01/REG_regulated-drugs.pdf . live . https://web.archive.org/web/20170127230917/http://healthvermont.gov/sites/default/files/documents/2017/01/REG_regulated-drugs.pdf . 27 January 2017 .

This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "HU-210".

Except where otherwise indicated, Everything.Explained.Today is © Copyright 2009-2024, A B Cryer, All Rights Reserved. Cookie policy.