THC hemisuccinate
{{Short description|Synthetic derivative of tetrahydrocannabinol}}
{{cs1 config|name-list-style=vanc|display-authors=6}}
{{Drugbox
| IUPAC_name =
| image = THC-hemisuccinate_structure.png
| image_class = skin-invert-image
| width = 220
| pregnancy_category =
| legal_status =
| routes_of_administration =
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| metabolism =
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| CAS_number = 52855-15-9
| CAS_number_Ref = {{Cascite|correct|EPA}}
| PubChem = 162707
| ChemSpiderID = 142849
| ChEMBL =
| ChEBI =
| UNII =
| C=25 | H=34 | O=5
| smiles = CCCCCC1=CC2=C([C@@H]3C=C(CC[C@H]3C(O2)(C)C)C)C(=C1)OC(=O)CCC(=O)O
| StdInChI = 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
| StdInChIKey = 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.{{cite journal | vauthors = Elsohly MA, Little TL, Hikal A, Harland E, Stanford DF, Walker L | title = Rectal bioavailability of delta-9-tetrahydrocannabinol from various esters | journal = Pharmacology, Biochemistry, and Behavior | volume = 40 | issue = 3 | pages = 497–502 | date = November 1991 | pmid = 1666913 | doi = 10.1016/0091-3057(91)90353-4 | s2cid = 24650457 }}{{cite journal | vauthors = ElSohly MA, Stanford DF, Harland EC, Hikal AH, Walker LA, Little TL, Rider JN, Jones AB | title = Rectal bioavailability of delta-9-tetrahydrocannabinol from the hemisuccinate ester in monkeys | journal = Journal of Pharmaceutical Sciences | volume = 80 | issue = 10 | pages = 942–5 | date = October 1991 | pmid = 1664466 | doi = 10.1002/jps.2600801008 }}{{cite journal | vauthors = Upadhye SB, Kulkarni SJ, Majumdar S, Avery MA, Gul W, ElSohly MA, Repka MA | title = Preparation and characterization of inclusion complexes of a hemisuccinate ester prodrug of delta9-tetrahydrocannabinol with modified beta-cyclodextrins | journal = AAPS PharmSciTech | volume = 11 | issue = 2 | pages = 509–17 | date = June 2010 | pmid = 20333489 | doi = 10.1208/s12249-010-9401-4 | pmc = 2902337 }} In medical applications it has mainly been formulated as rectal suppositories.{{cite book | vauthors = Walker LA, Harland EC, Best AM, ElSohly MA | date = 1999 | chapter = Δ9-THC Hemisuccinate in Suppository Form as an Alternative to Oral and Smoked THC | veditors = Nahas GG, Sutin KM, Harvey D, Agurell S, Pace N, Cancro RN | title = Marihuana and Medicine | publisher = Humana Press | location = Totowa, NJ | doi = 10.1007/978-1-59259-710-9_13 }}{{cite journal | vauthors = Broom SL, Sufka KJ, Elsohly MA, Ross SA | date = 2001 | title = Analgesic and Reinforcing Properties of Δ9-THC-Hemisuccinate in Adjuvant-Arthritic Rats. | journal = Journal of Cannabis Therapeutics | volume = 1 | issue = 3–4 | pages = 171–182 | doi = 10.1300/J175v01n03_11 }}{{cite journal | vauthors = ElSohly MA, Gul W, Walker LA | title = Pharmacokinetics and Tolerability of Δ9-THC-Hemisuccinate in a Suppository Formulation as an Alternative to Capsules for the Systemic Delivery of Δ9-THC | journal = Medical Cannabis and Cannabinoids | volume = 1 | issue = 1 | pages = 44–53 | date = June 2018 | pmid = 34676321 | pmc = 8489354 | doi = 10.1159/000489037 }}