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Publication Title | Solubility of non-psychoactive cannabinoids in supercritical carbon dioxide and comparison with psychoactive cannabinoids

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J. of Supercritical Fluids 55 (2010) 603–608

Contents lists available at ScienceDirect

The Journal of Supercritical Fluids

journal homepage: www.elsevier.com/locate/supflu

Solubility of non-psychoactive cannabinoids in supercritical carbon dioxide and comparison with psychoactive cannabinoids

Helene Perrotin-Brunela,∗, Maaike C. Kroona, Maaike J.E. van Roosmalenb, Jaap van Spronsena, Cor J. Petersa,c, Geert-Jan Witkampa

a Laboratory for Process Equipment, Delft University of Technology, Leeghwaterstraat 44, 2628 CA Delft, The Netherlands b FeyeCon D&I B.V., Rijnkade 17a, 1382 GS Weesp, The Netherlands

c The Petroleum Institute, P.O. Box 2533, Abu Dhabi, United Arab Emirates

article info

Article history:

Received 27 May 2010

Received in revised form 6 September 2010 Accepted 15 September 2010

Keywords:

Solubility

Cannabidiol

Cannabigerol

Cannabinoids

Supercritical carbon dioxide Peng–Robinson equation of state Van der Waals mixing rules

1. Introduction

At present, there is a growing interest in natural medicinal com- pounds. Cannabis sativa L. is one of the oldest medicinal plants known [1]. Recently, the medicinal use of cannabis has been legal- ized in several countries [2]. Some of the medical purposes include, but are not limited to, multiple sclerosis, chronic pain, glaucoma, appetite stimulant, asthma and cardiovascular conditions, and as an antiemetic [3]. The active cannabinoids are present in the cannabis flower of the female species. In nature, these molecules occur in their acidic form. Under influence of heat or light, they loose the acidic group by release of a carbon dioxide molecule, a so-called decarboxylation reaction. In this way they become neutral cannabi- noids, some of which are psychoactive [1].

Each cannabinoid has different biological properties. The major active compound from cannabis, (−)- 9 -tetrahydrocannabinol ( 9-THC), is the most psychoactive one [4]. It has been registered for medical application in several countries. 9-THC is also often used as golden standard for pharmacological studies. Depending on the cannabis species, its amount can reach levels up to 18%,

∗ Corresponding author. Tel.: +31 152785561; fax: +31 152786975. E-mail addresses: h.perrotin-brunel@tudelft.nl, brunel helene@yahoo.fr

(H. Perrotin-Brunel).

0896-8446/$ – see front matter © 2010 Elsevier B.V. All rights reserved. doi:10.1016/j.supflu.2010.09.011

abstract

The solubilities of two different non-psychoactive cannabinoids i.e., cannabigerol (CBG) and cannabid- iol (CBD), in supercritical carbon dioxide (CO2 ) have been determined at 315, 326 and 334 K and in the pressure range from 11.3 to 20.6 MPa. These solubility data have been compared to the previously deter- mined solubilities of two psychoactive cannabinoids i.e., (−)- 9-tetrahydrocannabinol ( 9-THC) and cannabinol (CBN), in supercritical CO2. An analytical method with a quasi-flow apparatus was used for the experimental determination. Within the investigated temperature and pressure range, the molar solubility of CBG ranged from 1.17 to 1.91 × 10−4 and the molar solubility of CBD ranged from 0.88 to 2.69 × 10−4 . The solubility of the different cannabinoids in supercritical CO2 increases at 326 K in the fol- lowing order: 9 -THC < CBG < CBD < CBN. The solubility data were correlated using the Peng–Robinson equation of state in combination with Van der Waals mixing rules. Deviations between calculated results and the experimental data ranged from 0.81 to 6.35% absolute average relative deviation (AARD), except for CBD at 334 K, where the AARD was 18.4%.

© 2010 Elsevier B.V. All rights reserved.

for example in the Bedrocan cannabis plant [5]. When the plant is exposed to light or stored for a long time, the primary degra- dation product of 9-THC, called cannabinol (CBN), is formed. Its amount is limited in a fresh plant. CBN is a mildly psychoactive cannabinoid, and is perceived to be sedative or stupefying [6,7]. Another cannabinoid that can be present in cannabis in significant amounts is cannabidiol (CBD). Depending on the plant species, it can reach up to 6%, for example in the Bediol cannabis plant [8]. CBD is not psychoactive, although it may modulate the euphoric effects of 9-THC to some extent [9]. Medically, it appears to relieve con- vulsion, inflammation, anxiety, and nausea. The non-psychoactive cannabinoid cannabigerol (CBG) has been studied less in phar- maceutical investigations than the three previous ones. However, some studies have shown that it may lower blood pressure in rats. It also has analgesic and anti-inflammatory effects [10]. The chemical structures of these four different cannabinoids, includ- ing their molecular weights and melting points [11], are shown in Table 1.

The availability of the various cannabinoids as pure compounds is of great importance for pharmaceutical studies and the devel- opment of new medicines. Indeed, most of the controlled studies have been carried out with pure 9-THC and do not mimic the situation where cannabis is smoked. As CBD and CBG have anal- gesic and anti-inflammatory effects, these compounds may also be used in drugs [10]. To develop such medicines, pure CBD and CBG

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