ChemInform Abstract: Stereocontrol in Organic Synthesis Using the Diphenylphosphoryl Group

Clayden, Jonathan; Warren, Stuart

doi:10.1002/chin.199621261

Cited by 1 publication

(1 citation statement)

References 1 publication

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Our in vitro analysis, designed to simulate oral conditions of chewing, demonstrated that chewing LAN or AN with slaked lime decreased the levels of muscarinic esters, arecoline and guvacoline via hydrolysis and increased the levels of the carboxylic GABAergic uptake inhibitor metabolites, arecaidine consistent with previous studies. 4 , 5 , 45 , 46 , 47 , 48 Guvacine levels were increased in assays of AN and not significantly increased in assays of LAN. Other functionally active unknown compounds may have been produced by hydrolysis although the mutagenic compound, nitrosoguvacoline, was not detected.…”

Section: Discussionmentioning

confidence: 83%

Towards a replacement therapy for stimulant betel quid dependence: A proof of concept study

Osborne,

Pasupuleti,

Lee

et al. 2024

Addiction Biology

View full text Add to dashboard Cite

Stimulant betel quid (SBQ) containing Piper betle leaf (L), green unripe Areca catechu nut (AN) and the alkalizing agent, slaked lime, is an addictive, carcinogenic stimulant, with no pharmacotherapy, chewed by millions of people in the Asia/Pacific region. We compared the in vivo physiological profile of chewing (1) non‐stimulant P. betle leaf+AN (LAN), (2) SBQ utilizing slaked lime and (3) a novel SBQ utilizing Mg(OH)2, as an alkalizing agent, by measuring physiological parameters of intoxication and these were correlated with in vitro levels of alkaloids measured by UHPLC–MS/MS. Chewing LAN, which contains high levels of arecoline, had no stimulatory physiological effect. Chewing SBQ containing slaked lime or novel SBQ containing Mg(OH)2, induced equivalent stimulatory physiological responses. In vitro, slaked lime hydrolyzed muscarinic esters in LAN while Mg(OH)2 did not. The physiological stimulation induced by chewing both SBQ and the lack of physiology to chewing LAN can be explained by changes in lipid solubility of phytochemicals induced by mouth pH during chewing of basic SBQ or acidic LAN. Since antiquity people have added slaked lime to SBQ to enhance absorption of phyto‐chemicals across oral membranes to stimulate physiology. The same physiological changes can be induced by substituting slaked lime for less physically and chemically destructive bases. If attitudes regarding SBQ dependence can advance towards the more progressive attitudes already used to help smokers quit tobacco, modern chemistry has the potential to make chewing SBQ safer and quitting programs may become more accessible and efficacious.

show abstract