Preparative Isolation of Cannabinoids from Cannabis sativa ...

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Preparative Isolation of Cannabinoids from Cannabis sativa by Centrifugal Partition Chromatography

Article in Journal of Liquid Chromatography & Related Technologies ? December 2004

DOI: 10.1081/JLC-200028170

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Cannabis; extracting the medicine

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Arno Hazekamp Cannabis; extracting the medicine Proefschrift Universiteit Leiden ISBN 978-90-9021997-4 Printed by PrintPartners Ipskamp B.V., Amsterdam, The Netherlands

Paper cover: Cannabis Pur 100% (250 grams) from Grafisch Papier, The Nederlands. Photo cover: Dutch medicinal cannabis, variety "Bedrocan". ii

Cannabis; extracting the medicine

Proefschrift Ter verkrijging van de graad van Doctor aan de Universiteit Leiden, op gezag van de Rector Magnificus prof. mr. P. F. van der Heijden, hoogleraar in de faculteit der Rechtsgeleerdheid, volgens besluit van het College voor Promoties te verdedigen op woensdag 5 september 2007 klokke 15.00 uur

door

Arno Hazekamp Geboren op 15 maart 1976

te Bilthoven

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Promotiecommissie

Promotor

Prof. dr. R. Verpoorte

Referent

Dr. C. Giroud (Institut Universitaire de M?decine L?gale, Lausanne, Switzerland)

Overige leden

Prof. dr. M. Danhof Prof. dr. C. A. M. J. J. van den Hondel Prof. dr. J. J. C. Scheffer Dr. R. van der Heijden

The printing of this thesis was supported by grants of the following sponsors:

Storz & Bickel GmbH & Co. KG, Tuttlingen, Germany Farmalyse BV, Zaandam, The Netherlands Nationaal MS-fonds, Maassluis, The Netherlands Multidisciplinary Association for Psychedelic Studies (MAPS), California, USA Bedrocan BV, Veendam, The Netherlands Mr. Michael Sautman, California, USA

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Contents

Chapter 1 A general introduction to cannabis as medicine

1

Chapter 2 An evaluation of the quality of medicinal grade cannabis

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in the Netherlands

Chapter 3 Preparative isolation of cannabinoids from Cannabis sativa

39

by centrifugal partition chromatography

Chapter 4 Quantitative analysis of cannabinoids from Cannabis sativa

53

using 1H-NMR

Chapter 5 Synthesis and spectroscopic characterization of cannabinolic acid

63

Chapter 6 Chromatographic and spectroscopic data of cannabinoids from

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Cannabis sativa L.

Chapter 7 Development and validation of a reversed-phase HPLC method for

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the determination of major cannabinoids from medicinal grade

Cannabis sativa plant material

Chapter 8 Cannabis tea revisited: a systematic evaluation of the cannabinoid

107

composition of cannabis tea

Chapter 9 Structure elucidation of the tetrahydrocannabinol complex with

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randomly methylated beta-cyclodextrin

Chapter 10 Evaluation of a vaporizing device (Volcano?) for the pulmonary

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administration of tetrahydrocannabinol

Concluding remarks and perspectives

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Summary

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Samenvatting

157

References

165

Acknowledgements

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Curriculum vitae

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List of publications

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CHAPTER 1 A general introduction to cannabis as medicine

? ? ? Arno Hazekamp, Renee Ruhaak

? ? Leiden University, Department of Pharmacognosy, Gorlaeus Laboratories

Leiden, The Netherlands

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