HU-210

HU-210
Clinical data
Other names	1,1-Dimethylheptyl- 11-hydroxy- tetrahydrocannabinol
Legal status
Legal status	CA: Schedule II; UK: Class B; US: Schedule I;
Identifiers
	IUPAC name (6aR,10aR)-9-(hydroxymethyl)-6,6-dimethyl-3-(2-methyloctan-2-yl)-6H,6aH,7H,10H,10aH-benzo[c]isochromen-1-ol;
CAS Number	112830-95-2 ;
PubChem CID	9821569;
IUPHAR/BPS	731;
ChemSpider	7997318 ;
UNII	191042422P;
ChEMBL	ChEMBL307696 ;
PDB ligand	A1H66 (PDBe, RCSB PDB);
CompTox Dashboard (EPA)	DTXSID30150188 ;
Chemical and physical data
Formula	C25H38O3
Molar mass	386.576 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCCCCCC(C)(C)C1=CC2=C([C@@H]3CC(=CC[C@H]3C(O2)(C)C)CO)C(=C1)O;
	InChI 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 ; Key:SSQJFGMEZBFMNV-WOJBJXKFSA-N ;
	(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]

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

[USDOJ-1] Cite error: The named reference USDOJ was invoked but never defined (see the help page).

[Mechoulam_et_al_1990-2] 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, 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.

[pmid1317925-6] 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.

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