Acetone → Tetrahydrocannabinol

HRID 1762416Notes

Reaction equation

HRID 1762416 reaction equation
[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[CH:7]=[C:8]([OH:23])[C:9]2[C:10]3[CH:11]=[C:12]([CH3:22])[CH:13]=[CH:14][C:15]=3[C:16]([CH3:21])([CH3:20])[O:17][C:18]=2[CH:19]=1.CC(C)=O>C([O-])(O)=O.[Na+].O1CCOCC1>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[CH:7]=[C:8]([OH:23])[C:9]2[C@@H:10]3[CH:11]=[C:12]([CH3:22])[CH2:13][CH2:14][C@H:15]3[C:16]([CH3:21])([CH3:20])[O:17][C:18]=2[CH:19]=1

Participants

5

Reactant 2

HCID 180AcetoneHCID 2543Cannabinol

Product 1

HCID 16078Tetrahydrocannabinol

Reagents, catalysts & solvents 2

HCID 312751,4-DioxaneSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

One hundred mg of human IgG were dissolved in 7 ml of 0.2M NaHCO3, pH 9.6, and 108 mg of a cannabinol derivative having the formula ##STR5## in 2 ml of dioxane were added. Nine additional ml of dioxane were added, and the mixture was mixed intermittently for 4 hours at 4° C., after which 180 ml of cold acetone were added. The mixture was centrifuged for 10 minutes at 2,000×g, and the pellet was washed once with 20 ml of cold acetone. Following centrifugation for 10 minutes at 2,000×g, the pellet was resuspended in 10 ml of phosphate buffered saline (PBS). Dialysis was carried out for 3 days at 4° C. against 2 changes per day of 1000-ml volumes of PBS, to produce a THC-human IgG conjugate.

Workup

  1. additionwere added
  2. additionthe mixture was mixed intermittently for 4 hours at 4° C.
  3. washthe pellet was washed once with 20 ml of cold acetone
  4. customfor 10 minutes
  5. customDialysis
  6. waitwas carried out for 3 days at 4° C. against 2 changes per day of 1000-ml volumes of PBS

Sources & evidence

ORD record
ord-b4a91bc0876843d6a92c2912e8675fde
Source dataset
uspto-grants-1989_05
Patent number
US04833073

Reaction notes

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