Synthesis of deuterium labeled cannabinoids

Banijamali, Ali R.; Aboutaleb, Nageh; Schyf, Cornelis J. Van der; Charalambous, Avgui; Makriyannis, Alexandros

doi:10.1002/jlcr.2580250109

Cited by 18 publications

(10 citation statements)

References 10 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Deuterated D 8 -THC was synthesized using procedures developed in our laboratory (Banijamali et al, 1988;Banijamali et al, 1998), where deuterium labels were specifically placed at the 2 and 4 positions in the rigid tricyclic ring system (Fig. 2).…”

Section: Sample Preparationmentioning

confidence: 99%

Albumin enhances the diffusion of lipophilic drugs into the membrane bilayer

2005

Self Cite

View full text Add to dashboard Cite

Section: Sample Preparationmentioning

confidence: 99%

Albumin enhances the diffusion of lipophilic drugs into the membrane bilayer

2005

Self Cite

View full text Add to dashboard Cite

“…This experiment required the strategic introduction of 2 H labels in different positions of the tricyclic cannabinoid ring system. To that effect, we synthesized (-)delta-9-THC with specific 2 H labels in each of the 2, 4, 8 alpha, 8 beta, 11-CH 3 , 10, and 10a positions (Banijamali et al 1987). The labeled drug molecule was then introduced in DPPC bilayers.…”

Section: The Orientation Of (-)-Delta-9-thc In Dppc Bilayersmentioning

confidence: 99%

Structure-Activity Relationships of Tricyclic and Nonclassical Bicyclic Cannabinoids

Mr²

1987

PsycEXTRA Dataset

View full text Add to dashboard Cite

The Research Analysis and Utilization System (RAUS) is designed to serve four functions: Collect and systematically classify the findings of all intramural and extramural research supported by the National Institute on Drug Abuse (NIDA); Evaluate the findings in selected areas of particular interest and formulate a state-of-the-art review by a panel of scientific peers; Disseminate findings to researchers in the field and to administrators, planners, instructors, and other interested persons; Provide a feedback mechanism to NIDA staff and planners so that the administration and monitoring of the NIDA research program reflect the very latest knowledge gleaned from research in the field. Since the number of research topics that can be intensively reviewed annually is limited, four subject areas are chosen each year to undergo a thorough examination. Distinguished scientists are invited to participate. Each scientist is provided reports from NIDA-funded research and asked to add information derived from the literature and his or her own research and to prepare a comprehensive, state-of-the-art review paper on an assigned topic. These papers, together with a summary of the discussions which take place at the review meeting, make up a RAUS Review Report in the NIDA Research Monograph series. In recent years a large number of reviews and books have appeared summarizing research advances in the chemistry, pharmacology, toxicology, metabolism, and distribution of cannabinoids and their synthetic analogs. Yet the volume of research on structure-activity relationships of cannabinoids appears to have decreased. In order to evaluate NIDA's current research program on cannabinoids, to rekindle interest in this critical area, and to focus attention on profitable avenues for future research, NIDA found it timely to bring together experts on the structure-activity relationships of cannabinoids for a comprehensive review. v

show abstract

“…The cannabinoid-membrane interactions presumably induce changes in the functions of a number of these proteins and thus produce a variety of physiological effects. Experimental evidence for a mechanism of action involving cannabinoid-phospholipid interactions came from calorimetrie measure--33-ments (Bach et al 1976;Bruggeman and Melchior 1983;Burstein et al 1986;Makriyannis et al 1987;Van der Schyf et al 1988), electron spin resonance exper iments Gill 1976), Ή-NMR (Kriwacki thesis), fluores cence (Kriwacki 1986) and solid state 2 H-NMR (Makriyannis et al 1990).…”

Section: Isolation Of Synaptic Plasma Membranesmentioning

confidence: 99%

“…A 8 -THC, Me-A 8 -THC, 5'-I-A 8 -THC and 5'-I-Me-A 8 -THC were synthesized in our laboratories using methods reported elsewhere (Banijamali et al 1988;Charalambous et al 1990). CP 55,243 and CP 55,244 were kindly provided by Pfizer.…”

mentioning

confidence: 99%

See 1 more Smart Citation

Cannabinoid and anesthetic steroid interactions with membranes

Μαυρομούστακος¹,

Mavromoustakos²

View full text Add to dashboard Cite

Classical cannabinoids possessing a phenolic hydroxyl group 39 Classical cannabinoids lacking the phenolic hydroxyl group 43 -vii-Metabolites of THC 53 Tricyclic compounds with more than two hydroxyl groups 57 CONCLUSIONS STUDY OF TOPOGRAPHY OF CANNABINOIDS IN MEMBRANES US-ING X-RAY DIFFRACTION CANNABINOID LOCATION IN DMPC BILAYER Partially hydrated multilamellar vesicles Small and wide angle x-ray diffraction Temperature and humidity dependences of d-spacing Determination of the structure factor signs Electron density profile calculation Absolute electron density scale determination Results 82 Discussion 86 LOCATION OF CANNABINOIDS IN UNSATURATED LIPID BILAYERS AND BILAYERS FROM BRAIN PHOSPHOLIPID EXTRACT 88 D-spacing versus Temperature 93 Results 93 Discussion 99 LOCATION OF THE METHYLATED ANALOG OF THC IN DIFFERENT LIPID BILAYERS 100 D-spacing versus temperature 100 Results 100 -Vili-LOCATION OF THC AND ITS METHYLATED ANALOG IN SPHINGO-MYELIN 109 Results 109 Discussion 115 SMALL ANGLE X-RAY DIFFRACTION FROM FULLY HYDRATED BILAYERS Results CONCLUSIONS DYNAMIC PROPERTIES OF THE CANNABINOIDS IN MEMBRANE BILAYERS RESULTS AND DISCUSSION Spectra of preparations of DPPC deuterated at the head group Spectra of preparations of DPPC deuterated at the alpha methylene in acyl chains Spectra of preparations of DPPC deuterated at the seven position of the acyl chains 129 Spectra of preparations of DPPC deuterated at the terminal methyl groups of the acyl chains 132 Comparison of quadrupolar splitting values 135 CONCLUSIONS 137 EFFECTS OF ANESTHETIC STEROIDS ON THERMOTROPIC PROP-ERTIES OF MODEL MEMBRANES 140 -IX-LITERATURE REVIEW 140 RESULTS AND DISCUSSION 144 Effect of the equilibration conditions on the thermotropic properties of DPPC/alphaxalone Effects of the two steroids on the thermotropic properties of model membranes DPPC, DPPE, DOPC and Sphingomyelin liposomes DPPC, POPC and DPPE bilayer containing cholesterol Structurally Related Pregnane Analogs CONCLUSIONS TOPOGRAPHY OF ANESTHETIC STEROIDS IN MODEL MEMBRANES DIFFERENTIAL SCANNING CALORIMETRY X-RAY DIFFRACTION Temperature dependence of d-spacing Site of alphaxalone in the bilayer 178 Site of the inactive steroid in the bilayer 186 CONCLUSIONS 188 DYNAMIC PROPERTIES OF ANESTHETIC STEROIDS IN MEMBRANE BILAYERS 189 RESULTS AND DISCUSSION 189 Effects of anesthetic steroids on DPPC chains 190

show abstract

Synthesis of deuterium labeled cannabinoids

Cited by 18 publications

References 10 publications

Albumin enhances the diffusion of lipophilic drugs into the membrane bilayer

Albumin enhances the diffusion of lipophilic drugs into the membrane bilayer

Structure-Activity Relationships of Tricyclic and Nonclassical Bicyclic Cannabinoids

Cannabinoid and anesthetic steroid interactions with membranes

Contact Info

Product

Resources

About