THC hemisuccinate

THC hemisuccinate
Identifiers
IUPAC name
  • 4-[[(6aR,10aR)-6,6,9-trimethyl-3-pentyl-6a,7,8,10a-tetrahydrobenzo[c]chromen-1-yl]oxy]-4-oxobutanoic acid
CAS Number
PubChem CID
ChemSpider
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC25H34O5
Molar mass414.542 g·mol−1
3D model (JSmol)
SMILES
  • CCCCCC1=CC2=C([C@@H]3C=C(CC[C@H]3C(O2)(C)C)C)C(=C1)OC(=O)CCC(=O)O
InChI
  • InChI=1S/C25H34O5/c1-5-6-7-8-17-14-20(29-23(28)12-11-22(26)27)24-18-13-16(2)9-10-19(18)25(3,4)30-21(24)15-17/h13-15,18-19H,5-12H2,1-4H3,(H,26,27)/t18-,19-/m1/s1
  • Key:YVOODUUYDJKFDY-RTBURBONSA-N

THC hemisuccinate (Δ9-THC-O-hemisuccinate, Dronabinol hemisuccinate) is a synthetic derivative of tetrahydrocannabinol, developed in the 1990s. It is a water-soluble prodrug ester which is converted into THC inside the body, and was developed to overcome the poor bioavailability of THC when taken by non-inhaled routes of administration.[1][2][3]

See also

References

  1. ↑ Elsohly MA, Little TL, Hikal A, Harland E, Stanford DF, Walker L (November 1991). "Rectal bioavailability of delta-9-tetrahydrocannabinol from various esters". Pharmacology, Biochemistry, and Behavior. 40 (3): 497–502. doi:10.1016/0091-3057(91)90353-4. PMID 1666913.
  2. ↑ ElSohly MA, Stanford DF, Harland EC, Hikal AH, Walker LA, Little TL, et al. (October 1991). "Rectal bioavailability of delta-9-tetrahydrocannabinol from the hemisuccinate ester in monkeys". Journal of Pharmaceutical Sciences. 80 (10): 942–5. doi:10.1002/jps.2600801008. PMID 1664466.
  3. ↑ Upadhye SB, Kulkarni SJ, Majumdar S, Avery MA, Gul W, ElSohly MA, Repka MA (June 2010). "Preparation and characterization of inclusion complexes of a hemisuccinate ester prodrug of delta9-tetrahydrocannabinol with modified beta-cyclodextrins". AAPS PharmSciTech. 11 (2): 509–17. doi:10.1208/s12249-010-9401-4. PMC 2902337. PMID 20333489.
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