HU-210

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
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 and 0.52 nM at CB2 in cloned human cannabinoid receptors[7] compared to delta-9-THC of 40.7 nM at CB1. [8] 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.

  1. ^ Cite error: The named reference USDOJ was invoked but never defined (see the help page).
  2. ^ 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, Consroe P (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.