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HU-210

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HU-210
Clinical data
Other names1,1-Dimethylheptyl- 11-hydroxy- tetrahydrocannabinol
Legal status
Legal status
Identifiers
  • (6aR,10aR)-9-(hydroxymethyl)-6,6-dimethyl-3-(2-methyloctan-2-yl)-6H,6aH,7H,10H,10aH-benzo[c]isochromen-1-ol
CAS Number
PubChem CID
IUPHAR/BPS
ChemSpider
UNII
ChEMBL
PDB ligand
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC25H38O3
Molar mass386.576 g·mol−1
3D model (JSmol)
  • CCCCCCC(C)(C)C1=CC2=C([C@@H]3CC(=CC[C@H]3C(O2)(C)C)CO)C(=C1)O
  • 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/h10,14-15,19-20,26-27H,6-9,11-13,16H2,1-5H3/t19-,20-/m1/s1 ☒N
  • Key:SSQJFGMEZBFMNV-WOJBJXKFSA-N ☒N
 ☒NcheckY (what is this?)  (verify)

HU-210 is a synthetic cannabinoid that was first synthesized in 1988 from (1R,5S)-myrtenol[2] by a group led by Raphael Mechoulam at the Hebrew University.[3][4][5] HU-210 is 100 to 800 times more potent than natural THC from cannabis and has an extended duration of action.[6] HU-210 has a binding affinity of 0.061 nM at CB1 receptors[7] compared to 40.7 nM for Δ9-THC.[8] The binding pose of HU-210 to the CB1 receptor is similar to other synthetic cannabinoids.[9]

Effects and research

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HU-210, the (–) enantiomer, is an ultrapotent cannabinoid, while its (+) enantiomer HU-211 is not a cannabinoid, but an NMDA antagonist with neuroprotective effects.[10][11]

HU-210 has an oral LD50 of 5,000 mg/kg in rats and 14,200 mg/kg in rabbits,[12] and an LDLO (lowest lethal dose) of 143 mg/kg in humans.[12] This is more toxic than Δ8-THC; in monkeys and dogs, 9,000 mg/kg of Δ8-THC was nonlethal.[13][14]

Chemistry

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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).[2]

HU-210 synthesis
HU-210 synthesis
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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,[15] so the signatory countries to these international drug control treaties are not required by said treaties to control HU-210.

New Zealand

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HU-210 is banned in New Zealand as of 8 May 2014.[16]

United States

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HU-210 is not explicitly listed in the list of scheduled controlled substances in the USA.[17] 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.[18] A version of the document (updated in 2013), now in PDF form, exists on the DEA Office of Diversion Control's website.[1] 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.[19]

Alabama

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HU-210 is a Schedule I controlled substance in Alabama.[20]

(4)a. A synthetic controlled substance that is any material, mixture, or preparation that contains any quantity of the following chemical compounds, their salts, isomers and salts of isomers, unless specifically excepted, whenever the existence of these salts, isomers and salts of isomers is possible within the specific chemical designation or compound:

...

9. (6aR, 10aR)-9-(hydroxymethyl)-6,6-dimethyl-3-(2-methyloctan-2-yl)-6a,7,10,10a-tetrahydrobenzo[c]chromen-1-ol, some trade or other names: HU-210.

Florida

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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.[21]

(c) Unless specifically excepted or unless listed in another schedule, any material, compound, mixture, or preparation that contains any quantity of the following hallucinogenic substances or that contains any of their salts, isomers, including optical, positional, or geometric isomers, homologues, nitrogen-heterocyclic analogs, esters, ethers, and salts of isomers, homologues, nitrogen-heterocyclic analogs, esters, or ethers, if the existence of such salts, isomers, and salts of isomers is possible within the specific chemical designation or class description: ... 47. HU-210 [(6aR,10aR)-9-(Hydroxymethyl)-6,6-dimethyl-3-(2-methyloctan-2-yl)-6a,7,10,10a-tetrahydrobenzo[c]chromen-1-ol].

Vermont

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Effective January 1, 2016, HU-210 is a regulated drug in Vermont designated as a "Hallucinogenic Drug."[22]

See also

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References

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  1. ^ a b "HU-210" (PDF). Office of Diversion Control. Drug Enforcement Administration, U.S. Department of Justice. January 2013. Archived from the original (PDF) on 2016-12-28. 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"
  2. ^ a b Mechoulam R, Lander N, Zahalka J (January 1990). "Synthesis of the individual, pharmacologically distinct, enantiomers of a tetrahydrocannabinol derivative". Tetrahedron: Asymmetry. 1 (5): 315–318. doi:10.1016/S0957-4166(00)86322-3.
  3. ^ Mechoulam R, Feigenbaum JJ, Lander N, Segal M, Järbe TU, Hiltunen AJ, et al. (September 1988). "Enantiomeric cannabinoids: stereospecificity of psychotropic activity". Experientia. 44 (9): 762–4. doi:10.1007/BF01959156. PMID 3416993. S2CID 19589995.
  4. ^ Little PJ, Compton DR, Mechoulam R, Martin BR (March 1989). "Stereochemical effects of 11-OH-delta 8-THC-dimethylheptyl in mice and dogs". Pharmacology, Biochemistry, and Behavior. 32 (3): 661–6. doi:10.1016/0091-3057(89)90014-2. PMID 2544901. S2CID 140209484.
  5. ^ Järbe TU, Hiltunen AJ, Mechoulam R (September 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.
  6. ^ Devane WA, Breuer A, Sheskin T, Järbe TU, Eisen MS, Mechoulam R (May 1992). "A novel probe for the cannabinoid receptor". Journal of Medicinal Chemistry. 35 (11): 2065–9. doi:10.1021/jm00089a018. PMID 1317925.
  7. ^ Stern E, Lambert DM (August 2007). "Medicinal chemistry endeavors around the phytocannabinoids". Chemistry & Biodiversity. 4 (8): 1707–1728. doi:10.1002/cbdv.200790149. PMID 17712816. S2CID 24920412.
  8. ^ Bow EW, Rimoldi JM (2016). "The Structure-Function Relationships of Classical Cannabinoids: CB1/CB2 Modulation". Perspectives in Medicinal Chemistry. 8: 17–39. doi:10.4137/PMC.S32171. PMC 4927043. PMID 27398024.
  9. ^ Gloriam D, Thorsen T, Kulkarni Y, Sykes D, Bøggild A, Drace T, et al. (May 2024). "Structural basis of Δ9-THC analog activity at the Cannabinoid 1 receptor". Research Square. doi:10.21203/rs.3.rs-4277209/v1. PMC 11142349. PMID 38826401.
  10. ^ Howlett AC, Champion TM, Wilken GH, Mechoulam R (February 1990). "Stereochemical effects of 11-OH-delta 8-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. S2CID 28602221.
  11. ^ Darlington CL (October 2003). "Dexanabinol: a novel cannabinoid with neuroprotective properties". IDrugs. 6 (10): 976–9. OCLC 112453448. PMID 14534855.
  12. ^ a b "HU-210" (PDF). Material Safety Data Sheet. Cayman Chemical.
  13. ^ Thompson GR, Rosenkrantz H, Schaeppi UH, Braude MC (July 1973). "Comparison of acute oral toxicity of cannabinoids in rats, dogs and monkeys". Toxicology and Applied Pharmacology. 25 (3): 363–72. Bibcode:1973ToxAP..25..363T. doi:10.1016/0041-008X(73)90310-4. PMID 4199474.
  14. ^ "delta-8-Tetrahydrocannabinol". ChemIDplus. U.S. National Library of Medicine.
  15. ^ "International Drug Control Conventions". United Nations Office on Drugs and Crime. Archived from the original on 12 January 2018. Retrieved 3 May 2018.
  16. ^ "Synthetic cannabinoids: What they are". New Zealand Drug Foundation. Archived from the original on 2015-09-21. Retrieved 2015-07-18.
  17. ^ "PART 1308 - Section 1308.11 Schedule I". Office of Diversion Control. Drug Enforcement Administration, U.S. Department of Justice. Archived from the original on 27 August 2009. Retrieved 3 May 2018.
  18. ^ "Spice Cannabinoid - HU-210". Office of Diversion Control. Drug Enforcement Administration, U.S. Department of Justice. Archived from the original on 2012-01-17.
  19. ^ Lists of Scheduling Actions, Controlled Substances, and Regulated Chemicals (PDF). Drug and Chemical Evaluation Section, Diversion Control Division, Drug Enforcement Administration Division, U.S. Department of Justice. November 2024.
  20. ^ "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. Archived from the original on 4 March 2016. Retrieved 2 February 2017.
  21. ^ "Chapter 893: Drug Abuse Prevention and Control". The 2020 Florida Statutes. The Florida Legislature. Archived from the original on 14 March 2018. Retrieved 3 May 2018.
  22. ^ "Chapter 8 – Alcohol and Drug Abuse Subchapter 9: Regulated Drug Rule" (PDF). Code of Vermont Rules. Vermont Department of Health. 15 July 2017. Archived (PDF) from the original on 27 January 2017. Retrieved 3 May 2018.

Further reading

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