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9-Nor-9β-hydroxyhexahydrocannabinol

9-Nor-9β-hydroxyhexahydrocannabinol (9-Nor-9beta-HHC, sometimes incorrectly confused with 11-nor-9β-hydroxyhexahydrocannabinol)[1],is a cannabinoid first discovered from early modifications to the structure of THC, in a search for the simplest compound that could still fulfill the binding requirements to produce cannabis-like activity.[2][3]

9-Nor-9β-hydroxyhexahydrocannabinol
Identifiers
  • 6,6-Dimethyl-3-pentyl-6a,7,8,9,10,10a-hexahydrobenzo[c]chromene-1,9-diol
CAS Number
  • 52171-85-4 Y
PubChem CID
  • 6452587
ChemSpider
  • 23232433
UNII
  • NA3QQQ5D4S
CompTox Dashboard (EPA)
  • DTXSID30966529
Chemical and physical data
FormulaC20H30O3
Molar mass318.457 g·mol−1
3D model (JSmol)
  • Interactive image
  • CCCCCc1cc(c2c(c1)OC([C@H]3[C@H]2C[C@@H](CC3)O)(C)C)O
  • InChI=1S/C20H30O3/c1-4-5-6-7-13-10-17(22)19-15-12-14(21)8-9-16(15)20(2,3)23-18(19)11-13/h10-11,14-16,21-22H,4-9,12H2,1-3H3/t14-,15-,16-/m1/s1
  • Key:AAIHVZNCFQTVCA-BZUAXINKSA-N

11-Hydroxyhexahydrocannabinol is the structurally related methylene homologue of 11-Nor-9β-hydroxyhexahydrocannabinol that has been found as a minor active metabolite of tetrahydrocannabinol, and also a metabolite of the trace cannabinoid hexahydrocannabinol.[4]

See also

References

  1. ^ "9-Hydroxy-9-norhexahydrocannabinol".
  2. ^ Johnson MR, Althuis TH, Bindra JS, Harbert CA, Melvin LS, Milne GM (1980). Potent Analgetics Derived From 9-Nor-9β-Hydroxyhexahydrocannabinol. NIDA Research Monograph. Vol. 34. pp. 68−74.
  3. ^ Melvin LS, Johnson MR (1987). "Relationships of Tricyclic and Nonclassical Bicyclic Cannabinoids". In Rapaka RS, Makriyannis A (eds.). Structure-activity Relationships of the Cannabinoids. NIDA Research Monograph. Vol. 79. pp. 31–47.
  4. ^ Järbe TU, Hiltunen AJ, Lander N, Mechoulam R (August 1986). "Cannabimimetic activity (delta 1-THC cue) of cannabidiol monomethyl ether and two stereoisomeric hexahydrocannabinols in rats and pigeons". Pharmacology, Biochemistry, and Behavior. 25 (2): 393–9. doi:10.1016/0091-3057(86)90015-8. PMID 3020594. S2CID 28373651.

hydroxyhexahydrocannabinol, 9beta, sometimes, incorrectly, confused, with, hydroxyhexahydrocannabinol, cannabinoid, first, discovered, from, early, modifications, structure, search, simplest, compound, that, could, still, fulfill, binding, requirements, produc. 9 Nor 9b hydroxyhexahydrocannabinol 9 Nor 9beta HHC sometimes incorrectly confused with 11 nor 9b hydroxyhexahydrocannabinol 1 is a cannabinoid first discovered from early modifications to the structure of THC in a search for the simplest compound that could still fulfill the binding requirements to produce cannabis like activity 2 3 9 Nor 9b hydroxyhexahydrocannabinolIdentifiersIUPAC name 6 6 Dimethyl 3 pentyl 6a 7 8 9 10 10a hexahydrobenzo c chromene 1 9 diolCAS Number52171 85 4 YPubChem CID6452587ChemSpider23232433UNIINA3QQQ5D4SCompTox Dashboard EPA DTXSID30966529Chemical and physical dataFormulaC 20H 30O 3Molar mass318 457 g mol 13D model JSmol Interactive imageSMILES CCCCCc1cc c2c c1 OC C H 3 C H 2C C H CC3 O C C OInChI InChI 1S C20H30O3 c1 4 5 6 7 13 10 17 22 19 15 12 14 21 8 9 16 15 20 2 3 23 18 19 11 13 h10 11 14 16 21 22H 4 9 12H2 1 3H3 t14 15 16 m1 s1Key AAIHVZNCFQTVCA BZUAXINKSA N11 Hydroxyhexahydrocannabinol is the structurally related methylene homologue of 11 Nor 9b hydroxyhexahydrocannabinol that has been found as a minor active metabolite of tetrahydrocannabinol and also a metabolite of the trace cannabinoid hexahydrocannabinol 4 See also EditAM 2389 9 Hydroxyhexahydrocannabinol Hexahydrocannabinol 11 Hydroxyhexahydrocannabinol HU 243 NabiloneReferences Edit 9 Hydroxy 9 norhexahydrocannabinol Johnson MR Althuis TH Bindra JS Harbert CA Melvin LS Milne GM 1980 Potent Analgetics Derived From 9 Nor 9b Hydroxyhexahydrocannabinol NIDA Research Monograph Vol 34 pp 68 74 Melvin LS Johnson MR 1987 Relationships of Tricyclic and Nonclassical Bicyclic Cannabinoids In Rapaka RS Makriyannis A eds Structure activity Relationships of the Cannabinoids NIDA Research Monograph Vol 79 pp 31 47 Jarbe TU Hiltunen AJ Lander N Mechoulam R August 1986 Cannabimimetic activity delta 1 THC cue of cannabidiol monomethyl ether and two stereoisomeric hexahydrocannabinols in rats and pigeons Pharmacology Biochemistry and Behavior 25 2 393 9 doi 10 1016 0091 3057 86 90015 8 PMID 3020594 S2CID 28373651 Retrieved from https en wikipedia org w index php title 9 Nor 9b hydroxyhexahydrocannabinol amp oldid 1085862521, wikipedia, wiki, book, books, library,

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