17766-02-8Relevant articles and documents
Δ9-cis-Tetrahydrocannabinol: Natural Occurrence, Chirality, and Pharmacology
Allegrone, Gianna,Appendino, Giovanni,Botta, Bruno,Caprioglio, Diego,Carreira, Erick M.,Chicca, Andrea,Erni, Reto,Gasparrini, Francesco,Gertsch, Jürg,Grassi, Giulio,Mazzoccanti, Giulia,Pollastro, Federica,Reynoso-Moreno, Ines,Schafroth, Michael A.
supporting information, p. 2502 - 2510 (2021/08/16)
Thecis-stereoisomers of Δ9-THC [(?)- 3 and (+)- 3 ] were identified and quantified in a series of low-THC-containing varieties ofCannabis sativaregistered in Europe as fiber hemp and in research accessions of cannabis. While Δ9-cis-THC ( 3 ) occurs in cannabis fiber hemp in the concentration range of (?)-Δ9-trans-THC [(?)- 1 ], it was undetectable in a sample of high-THC-containing medicinal cannabis. Natural Δ9-cis-THC ( 3 ) is scalemic (ca. 80-90% enantiomeric purity), and the absolute configuration of the major enantiomer was established as 6aS,10aR[(?)- 3 ] by chiral chromatographic comparison with a sample available by asymmetric synthesis. The major enantiomer, (?)-Δ9-cis-THC [(?)- 3 ], was characterized as a partial cannabinoid agonist in vitro and elicited a full tetrad response in mice at 50 mg/kg doses. The current legal discrimination between narcotic and non-narcotic cannabis varieties centers on the contents of “Δ9-THC and isomers” and needs therefore revision, or at least a more specific wording, to account for the presence of Δ9-cis-THCs [(+)- 3 and (?)- 3 ] in cannabis fiber hemp varieties.
(+)-TRANS TETRAHYDROCANNABINOL ((+)-TRANS-THC) FOR USE AS A MEDICAMENT
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, (2021/04/30)
The present invention relates to a tetrahydrocannabinol (THC) type cannabinoid compound for use as a medicament. The THC-type cannabinoid is an enantiomer of the (-)-trans- tetrahydrocannabinol which is a naturally occurring cannabinoid that can be found in cannabis plant strains which have been bred to yield THC as the dominant cannabinoid. The particular enantiomer (+)-trans tetrahydrocannabinol has been found to have properties which are different from the naturally occurring (-)-trans-THC. The cannabinoid (+)-trans-THC has been found to occur in low concentrations in particular cannabis plant strains. Furthermore, the cannabinoid can be produced by synthetic means.
CATALYTIC CANNABINOID PROCESSES AND PRECURSORS
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Page/Page column 28; 32-33; 50, (2020/12/07)
The present disclosure relates to new cannabinoid sulfonate esters and processes for their use to prepare cannabinoids. The disclosure also relates to the use of catalysts and catalytic processes for the preparation of cannabinoids from the cannabinoid sulfonate esters.
Protecting group free enantiospecific total syntheses of structurally diverse natural products of the tetrahydrocannabinoid family
Dethe, Dattatraya H.,Erande, Rohan D.,Mahapatra, Samarpita,Das, Saikat,Kumar B., Vijay
supporting information, p. 2871 - 2873 (2015/03/03)
A simple, highly diastereoselective, Lewis acid catalyzed Friedel-Crafts coupling of a cyclic allylic alcohol with resorcinol derivatives has been developed. The method was applied for the enantiospecific total syntheses of structurally diverse natural products such as machaeriol-D, Δ8-THC, Δ9-THC, epi-perrottetinene and their analogues. Synthesis of both natural products and their enantiomers has been achieved with high atom economy, in a protecting group free manner and in less than 6 steps, the longest linear sequence, in a very good overall yield starting from R-(+) and S-(-)-limonene.
Stereodivergent total synthesis of Δ9-tetrahydrocannabinols
Schafroth, Michael A.,Zuccarello, Giuseppe,Krautwald, Simon,Sarlah, David,Carreira, Erick M.
, p. 13898 - 13901 (2015/02/18)
All four stereoisomers of Δ9-tetrahydrocannabinol (Δ9-THC) were synthesized in concise fashion using stereodivergent dual catalysis. Thus, following identical synthetic sequences and applying identical reaction conditions to the same
High-pressure access to the Δ9-cis - And Δ9-trans-tetrahydrocannabinols family
Minuti, Lucio,Ballerini, Eleonora
, p. 5392 - 5403 (2011/08/06)
Diels-Alder reactions of a range of 1-(alkoxy/alkyl-substituted phenyl)buta-1,3-dienes with methyl vinyl ketone and methyl acrylate carried out in ethanol as the reaction medium under 9 kbar pressure were investigated. The use of high pressure as the activating method of the Diels-Alder reactions allows the efficient and endodiastereoselective generation of a series of cis-cyclohexenyl-benzene cycloadducts, which are selectively converted into their trans-epimers. The cis-cyclohexenyl-benzenes and trans-cyclohexenyl- benzenes produced are useful precursors for accessing substituted privileged cis-6a,7,8,10a-tetrahydro-6H-benzo[c]chromene and trans-6a,7,8,10a-tetrahydro- 6H-benzo[c]chromene skeletons. The total syntheses of Δ9-cis- tetrahydrocannabinol (THC) and Δ9-trans-THC, through the use of selected Diels-Alder adducts, are described. Finally, a route for obtaining Δ9-trans-THC in both enantiomeric pure forms based on the (S)-(-)-1-amino-2-(methoxymethyl)pyrrolidine (SAMP)-hydrazone method is also reported.
Process for preparing synthetic cannabinoids
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, (2012/04/23)
The field of the invention is organic synthesis, more particularly a process for preparing cannabinoids. The process described is applicable to all stereoisomers and homologues of cannabinoids. For this purpose, the present patent application provides a process for preparing the abovementioned compounds in two or three chemical synthesis steps.
METHODS FOR PURIFYING TRANS-(-)-Δ9-TETRAHYDROCANNABINOL AND TRANS-(+)-Δ9-TETRAHYDROCANNABINOL
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Page/Page column 51-52, (2008/06/13)
Methods for making trans-(-)-Δ9-tetrahydrocannabinoI and trans-(+)-Δ9-tetrahydrocannabinol are disclosed herein. In one embodiment, a trans-(-)-Δ9-tetrahydrocannabinoI composition is prepared by allowing a composition comprising (±)-Δ9-tetrahydrocannabinol to separate on a chiral stationary phase to provide a trans-(-)-Δ9-tetrahydrocannabinoI composition comprising at least about 99% by weight of trans-(-)-Δ9-tetrahydrocannabinol based on the total amount of trans-(-)-Δ9-tetrahydrocannabinol and trans-(+)-Δ9-tetrahydrocannabinol. The invention also relates to methods for treating or preventing a condition such as pain comprising administering to a patient in need thereof an effective amount of a trans-(-)-Δ9-tetrahydrocannabinoI having a purity of at least about 98% based on the total weight of cannabinoids.
CANNABINOID ACTIVE PHARMACEUTICAL INGREDIENT FOR IMPROVED DOSAGE FORMS
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Page/Page column 85, (2010/11/25)
Pharmaceutical compositions comprising the cannabinoid active pharmaceutical ingredient, crystalline trans-(±)-Δ9-tetrahydrocannabinol, and formulations thereof are disclosed. The invention also relates to methods for treating or preventing a condition such as pain comprising administering to a patient in need thereof an effective amount of crystalline trans-(±)-Δ9-tetrahydrocannabinol. In specific embodiments, the crystalline trans-(±)-Δ9-tetrahydrocannabinol administered according to the methods for treating or preventing a condition such as pain can have a purity of at least about 98% based on the total weight of cannabinoids.
Tetrahydrocannabinol revisited: Synthetic approaches utilizing molybdenum catalysts
Malkov, Andrei V.,Kocovsky, Pavel
, p. 1257 - 1268 (2007/10/03)
Δ9-Tetrahydrocannabinol 1 and its isomers were synthesized via domino-type methodology. The first approach, leading to (±)-1, relies on the Mo(IV)-catalyzed, one-pot cascade reaction of citral (4) with olivetol (15), affording (±)-Δ9-tetrahydrocannabinol as a 69 : 31 mixture of the trans-(natural) and cis-isomers in 20% yield. The alternative approach, leading to natural (-)-1, commenced with epoxidation of (+)-limonene (R)-(+)-16; opening of the resulting cis-epoxide 17 with PhSeNa, followed by elimination, afforded tertiary alcohol 21, whose acetate 22 was treated with olivetol 15 in the presence of Mo(II) catalyst IV to afford (-)-1 in 52% yield.
