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THC hemisuccinate

Summary

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] In medical applications it has mainly been formulated as rectal suppositories.[4][5][6]

THC hemisuccinate
Identifiers
  • 4-[[(6aR,10aR)-6,6,9-trimethyl-3-pentyl-6a,7,8,10a-tetrahydrobenzo[c]chromen-1-yl]oxy]-4-oxobutanoic acid
CAS Number
  • 52855-15-9 checkY[EPA]
PubChem CID
  • 162707
ChemSpider
  • 142849
CompTox Dashboard (EPA)
  • DTXSID40200885 Edit this at Wikidata
Chemical and physical data
FormulaC25H34O5
Molar mass414.542 g·mol−1
3D model (JSmol)
  • Interactive image
  • CCCCCC1=CC2=C([C@@H]3C=C(CC[C@H]3C(O2)(C)C)C)C(=C1)OC(=O)CCC(=O)O
  • 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

See also edit


References edit

  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. S2CID 24650457.
  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, et al. (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.
  4. ^ Walker LA, Harland EC, Best AM, ElSohly MA (1999). "Δ9-THC Hemisuccinate in Suppository Form as an Alternative to Oral and Smoked THC". In Nahas GG, Sutin KM, Harvey D, Agurell S, Pace N, Cancro RN (eds.). Marihuana and Medicine. Totowa, NJ: Humana Press. doi:10.1007/978-1-59259-710-9_13.
  5. ^ Broom SL, Sufka KJ, Elsohly MA, Ross SA (2001). "Analgesic and Reinforcing Properties of Δ9-THC-Hemisuccinate in Adjuvant-Arthritic Rats". Journal of Cannabis Therapeutics. 1 (3–4): 171–182. doi:10.1300/J175v01n03_11.
  6. ^ ElSohly MA, Gul W, Walker LA (June 2018). "Pharmacokinetics and Tolerability of Δ9-THC-Hemisuccinate in a Suppository Formulation as an Alternative to Capsules for the Systemic Delivery of Δ9-THC". Medical Cannabis and Cannabinoids. 1 (1): 44–53. doi:10.1159/000489037. PMC 8489354. PMID 34676321.