Cannabinol → Tetrahydrocannabinol

HRID 1762415Notes

Reaction equation

HRID 1762415 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.Cl.CN(C)CCCN=C=NCC>CO.O>[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 2543CannabinolHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 16078Tetrahydrocannabinol

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

One hundred mg of a cannabinol derivative having the formula ##STR3## were dissolved in 20 ml of 30% methanol at pH 4.5. To this solution, 84 mg of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride were added and the pH was adjusted to 4.5. After mixing at room temperature for 30 minutes, 100 mg of methylated bovine serum albumin were added in 20 ml of water with mixing, and the pH was again adjusted to 4.5. The solution was mixed for 1 hour at room temperature and then overnight at 4° C., after which any unconjugated cannabinol derivative was removed by dialysis against 1000-ml volume changes of sodium phosphate buffer at 4° C., to produce a THC-methylated albumin conjugate.

Workup

  1. additionAfter mixing at room temperature for 30 minutes
  2. additionwith mixing
  3. additionThe solution was mixed for 1 hour at room temperature
  4. customovernight at 4° C., after which any unconjugated cannabinol derivative was removed by dialysis against 1000-ml volume changes of sodium phosphate buffer at 4° C.

Sources & evidence

ORD record
ord-2eee1e465cf7472885e474e750e1e0d7
Source dataset
uspto-grants-1989_05
Patent number
US04833073

Reaction notes

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