(6aR,10aR)-6,6,9-Trimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromen-1-yl 4-methylbenzenesulfonate

Gul, Waseem; Carvalho, Paulo; Berberich, David W.; Avery, Mitchell A.; ElSohly, Mahmoud A.

doi:10.1107/s1600536808022010

Cited by 6 publications

(5 citation statements)

References 3 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Δ 9 -THC is a 21-carbon terpenoid featuring an internal double bond (C9–C10) and two stereocenters (6a, 10a), with the levorotatory trans stereoisomer, (−)- trans -Δ 9 -THC (6a R ,10a R ; 1a ), occurring most abundantly in cannabis. The stereochemistry of Δ 9 -THC has been confirmed by synthesis and X-ray crystallography (as a benzenesulfonate ester) . Pure Δ 9 -THC is described as a “light yellow resinous oil” in The Merck Index and is a highly lipophilic substance with low vapor pressure and poor aqueous solubility (see Table ).…”

Section: Chemical Synthesis and Manufacturing Informationmentioning

confidence: 93%

See 1 more Smart Citation

Dark Classics in Chemical Neuroscience: Δ⁹-Tetrahydrocannabinol

Banister

Arnold

Connor

et al. 2019

ACS Chem. Neurosci.

View full text Add to dashboard Cite

Cannabis (Cannabis sativa) is the most widely used illicit drug in the world, with an estimated 192 million users globally. The main psychoactive component of cannabis is (−)-trans-Δ9-tetrahydrocannabinol (Δ9-THC), a compound with a diverse range of pharmacological actions. The unique and distinctive intoxication caused by Δ9-THC primarily reflects partial agonist action at central cannabinoid type 1 (CB1) receptors. Δ9-THC is an approved therapeutic treatment for a range of conditions, including chronic pain, chemotherapy-induced nausea and vomiting, and multiple sclerosis, and is being investigated in indications such as anorexia nervosa, agitation in dementia, and Tourette’s syndrome. It is available as a regulated pharmaceutical in products such as Marinol, Sativex, and Namisol as well as in an ever-increasing range of unregistered medicinal and recreational cannabis products. While cannabis is an ancient medicament, contemporary use is embroiled in legal, scientific, and social controversy, much of which relates to the potential hazards and benefits of Δ9-THC itself. Robust contemporary debate surrounds the therapeutic value of Δ9-THC in different diseases, its capacity to produce psychosis and cognitive impairment, and the addictive and “gateway” potential of the drug. This review will provide a profile of the chemistry, pharmacology, and therapeutic uses of Δ9-THC as well as the historical and societal import of this unique, distinctive, and ubiquitous psychoactive substance.

show abstract

Section: Chemical Synthesis and Manufacturing Informationmentioning

confidence: 93%

“…The stereochemistry of Δ 9 -THC has been confirmed by synthesis 32 and X-ray crystallography (as a benzenesulfonate ester). 33 Pure Δ 9 -THC is described as a "light yellow resinous oil" in The Merck Index 34 and is a highly lipophilic substance with low vapor pressure and poor aqueous solubility (see Table 1).…”

Section: Acs Chemical Neurosciencementioning

confidence: 99%

Dark Classics in Chemical Neuroscience: Δ⁹-Tetrahydrocannabinol

Banister

Arnold

Connor

et al. 2019

ACS Chem. Neurosci.

View full text Add to dashboard Cite

show abstract

“…The starting geometries of β-CD, CBD, and THC monomers were taken from the Cambridge Crystallographic Data Centre (CCDC) with deposition number 1,107,192 [ 29 ], 1,533,487 [ 30 ], and 702,456 [ 31 ], respectively. The pairwise initial arrangement of β-CDs, with facing secondary portals (Head-to-Head, HH) and facing primary portals (Tail-to-Tail, TT), were extracted from CCDC 166671 [ 32 ] and CCDC 864,041 [ 33 ], respectively.…”

Section: Methodsmentioning

confidence: 99%

Structural Investigation of Beta-Cyclodextrin Complexes with Cannabidiol and Delta-9-Tetrahydrocannabinol in 1:1 and 2:1 Host-Guest Stoichiometry: Molecular Docking and Density Functional Calculations

Triamchaisri

Toochinda

Lawtrakul

2023

IJMS

View full text Add to dashboard Cite

The complexation of β-cyclodextrin (β-CD) with cannabidiol (CBD) and Δ9-tetrahydrocannabinol (THC) was investigated using molecular docking and M062X/6-31G(d,p) calculations. The calculations suggested two possible complex formations of 1:1 and 2:1 host-guest molecular ratio of β-CD with CBD and THC. The preferred orientation of all complexes in this study exhibited the hydrogen bonding between hydroxy-substituted benzene ring of CBD and THC with the β-CD’s secondary hydroxy groups at the wide rim. The calculated complexation energies indicate that formation of the 2:1 complexes (−83.53 to −135.36 kcal/mol) was more energetically favorable and chemically stable than the 1:1 complexes (−30.00 to −34.92 kcal/mol). However, the deformation energies of the host and the guest components in the 2:1 complexes (37.47–96.91 kcal/mol) are much higher than those in the 1:1 complexes (3.49–8.69 kcal/mol), which means the formation processes of the 2:1 complexes are more difficult due to the rigidity of the dimeric β-CDs. Therefore, the inclusion complexes of β-CD with CBD and THC are more likely to be in 1:1 host-guest ratio than in 2:1 molecular ratio. The results of this study supported the experimental results that the complexation constant of 1:1 β-CD/CBD (Ks = 300 M−1) is greater than that of 2:1 β-CDs/CBD (Kss = 0.833 M−1). Altogether, this study introduced the fitting parameters that could indicate the stability of the molecular fits in complex formation of each stoichiometry host-guest ratio, which are important for the assessment of the inclusion mechanisms as well as the relationships of reactants and products in chemical reactions.

show abstract

“…For Á 9 -THC tosylate, see: Ducker (2004); Gul et al (2008). For a related process of photooxygenation, see: Motoyoshiya et al (1999); Griesbeck et al (2014).…”

Section: Related Literaturementioning

confidence: 99%

Crystal structure of (9S,10S)-10-ethoxy-9-hydroxy-6,6,9-trimethyl-3-pentyl-7,8,9,10-tetrahydro-6H-benzo[c]chromen-1-yl 4-methylbenzenesulfonate

et al. 2015

Self Cite

View full text Add to dashboard Cite

In the structure of the title compound, C30H40O6S, the cyclohexene and heterocyclic rings are linked by a double bond. The cyclohexene ring has a half-chair conformation (the methylene group adjacent to the hydroxy substituent lies above the remaining atoms) and the hydroxy and ethoxy groups have equatorial and bisectional dispositions, respectively. The heterocyclic ring has an envelope conformation (with the CMe2 C atom being the flap). The dihedral angle between the aromatic rings is 53.88 (10)°. A long intramolecular C—H⋯S interaction is noted. In the molecular packing, hydroxy-O—H⋯O(sulfonate) hydrogen bonds lead to a helical chain along [010]. Connections between chains are of the type methyl-C—H⋯O(sulfonate) and lead to supramolecular layers that lie parallel to (001). The studied crystal was an inversion twin.

show abstract

(6aR,10aR)-6,6,9-Trimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromen-1-yl 4-methylbenzenesulfonate

Cited by 6 publications

References 3 publications

Dark Classics in Chemical Neuroscience: Δ⁹-Tetrahydrocannabinol

Dark Classics in Chemical Neuroscience: Δ⁹-Tetrahydrocannabinol

Structural Investigation of Beta-Cyclodextrin Complexes with Cannabidiol and Delta-9-Tetrahydrocannabinol in 1:1 and 2:1 Host-Guest Stoichiometry: Molecular Docking and Density Functional Calculations

Crystal structure of (9S,10S)-10-ethoxy-9-hydroxy-6,6,9-trimethyl-3-pentyl-7,8,9,10-tetrahydro-6H-benzo[c]chromen-1-yl 4-methylbenzenesulfonate

Contact Info

Product

Resources

About

(6aR,10aR)-6,6,9-Trimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromen-1-yl 4-methylbenzenesulfonate

Cited by 6 publications

References 3 publications

Dark Classics in Chemical Neuroscience: Δ9-Tetrahydrocannabinol

Dark Classics in Chemical Neuroscience: Δ9-Tetrahydrocannabinol

Structural Investigation of Beta-Cyclodextrin Complexes with Cannabidiol and Delta-9-Tetrahydrocannabinol in 1:1 and 2:1 Host-Guest Stoichiometry: Molecular Docking and Density Functional Calculations

Crystal structure of (9S,10S)-10-ethoxy-9-hydroxy-6,6,9-trimethyl-3-pentyl-7,8,9,10-tetrahydro-6H-benzo[c]chromen-1-yl 4-methylbenzenesulfonate

Contact Info

Product

Resources

About

Dark Classics in Chemical Neuroscience: Δ⁹-Tetrahydrocannabinol

Dark Classics in Chemical Neuroscience: Δ⁹-Tetrahydrocannabinol