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Changing short description from "Chemical compound" to "Synthetic derivative of tetrahydrocannabinol" Tag: Shortdesc helper |
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{{Short description|Synthetic derivative of tetrahydrocannabinol}} |
{{Short description|Synthetic derivative of tetrahydrocannabinol}} |
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| IUPAC_name = <nowiki>4-[[(6aR,10aR)-6,6,9-trimethyl-3-pentyl-6a,7,8,10a-tetrahydrobenzo[c]chromen-1-yl]oxy]-4-oxobutanoic acid</nowiki> |
| IUPAC_name = <nowiki>4-[[(6aR,10aR)-6,6,9-trimethyl-3-pentyl-6a,7,8,10a-tetrahydrobenzo[c]chromen-1-yl]oxy]-4-oxobutanoic acid</nowiki> |
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'''THC hemisuccinate''' ('''Δ<sup>9</sup>-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 [[Route of administration|routes of administration]].<ref>{{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 }}</ref><ref>{{cite journal | vauthors = ElSohly MA, Stanford DF, Harland EC, Hikal AH, Walker LA, Little TL, Rider JN, Jones AB |
'''THC hemisuccinate''' ('''Δ<sup>9</sup>-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 [[Route of administration|routes of administration]].<ref>{{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 }}</ref><ref>{{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 }}</ref><ref>{{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 }}</ref> In medical applications it has mainly been formulated as [[rectal]] [[suppository|suppositorie]]s.<ref>{{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 }}</ref><ref>{{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 }}</ref><ref name="pmid34676321">{{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 }}</ref> |
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== See also == |
== See also == |
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* [[THC-O-acetate]] |
* [[THC-O-acetate]] |
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* [[THC-O-phosphate]] |
* [[THC-O-phosphate]] |
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* [[THC-VHS]] |
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* [[SP-111]] |
* [[SP-111]] |
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== References == |
== References == |
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Latest revision as of 06:13, 4 April 2024
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| Formula | C25H34O5 |
| Molar mass | 414.542 g·mol−1 |
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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]
See also[edit]
References[edit]
- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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.