16 10 25 Decarboxylation of THCA To Active THC

European Industrial Hemp Association (EIHA) paper on:
Decarboxylation of Tetrahydrocannabinolic acid (THCA)

to active THC
Authors: Kerstin Iffland, Michael Carus and Dr. med. Franjo Grotenhermen,
nova-Institut GmbH
Hürth (Germany), October 2016
Download this paper and further documents at: www.eiha.org
Responsible under press legislation (V.i.S.d.P.): Michael Carus | EIHA co/ nova-Institut GmbH |
Industriestraße 300 | 50354 Hürth | Germany | [email protected] | www.eiha.org
Motivation and Summary Results

The background of this study is as follows: On average After thorough research it became apparent that the most
hemp food stuffs contain up to 90% of the non- publications concerned with THCA decarboxylation to
psychoactive THCA. Nonetheless, regulation for THC THC after heating, were papers describing HPLC or GC
limits in food often uses total THC = THCA + THC. This methodologies and mostly only had one timepoint and
leads to an overestimation of the content of psychoactive temperature where they measured THCA and THC. Figure
THC in hemp food. The argument is that THCA can be 2 shows the results of the literature survey of studies
transformed in THC after heating (decarboxylation). This which had at least two timepoints and temperatures.
study analysed how relevant this conversion is in realistic
scenarios. What the graphic means
Taking the combined trendline into account, it would
Figure 2 shows the results for the complete decarboxylation need 3 hours at 100 °C to convert THCA fully into THC
depending on temperature and time. One realistic example and 4 hours at 98 °C. At high temperatures above 160 °C
scenario demonstrates, that the total THC measurement only about 10 minutes and at 200 °C only seconds are
method can lead to an overestimation of the content of needed to convert THCA fully into THC.
psychoactive THC of ca. 60%.
Limitations
It has to be pointed out that various techniques were used
Methodology in the THC measurements e.g. Veress and colleagues (1990)
To evaluate to what extent the THCA content of hemp used THCA in hexane on a glass plate whereas Taschwer et
food stuffs can influence their THC-levels, we performed al. (2015) used confiscated cannabis and heated it in a closed
a literature survey about the THCA carboxylation to cabinet. These differences could explain the discrepancy
THC (Fig. 1). In a second step we plotted these on a time- in some temperatures and times.
temperature graph using two different methods. On
the one hand, curve fitting with various mathematical Moreover, the different cited papers use various units of
functions was applied, where logarithmic trendlines had THC measurement e.g. mg/g vs. percentages. The graphic
the best R-squared values of 0.99. This was in line with shows the assumed complete THCA decarboxylation
the behaviour of a first order reaction and research about to THC, where we used the peaks shown in the graph
reaction kinetics of the decarboxylation reaction proves of Veress and colleagues (1990), for example, to indicate
this (Perrotin-Brunel et al., 2011). complete decarboxylation.
Side reactions affecting THC levels

It is important to note, that starting from ca. 157 °C THC
evaporates. Consequently, the peak THC levels given here,
heat are only present in the sample for a short amount of time.
- CO2 For instance, the highest THC content is reached at 145 °C
after 7 min, but after 40 min the total THC amount is
already halved (Veress et al., 1990). Taschwer and colleagues
(2015) show in their experiments peak THC levels after
Figure 1: Decarboxylation reaction of THCA to THC 3 min heating at 150 °C, but a return to near zero THC
(adapted from Perrotin-Brunel et al., 2011). percentages after 7 min.
1
Figure 2: Graph of various experiments measuring the complete THCA-decarboxylation depending on time and temperature. The bold dark blue line
represents a combination of the depicted experiments.
Apart from THC evaporation, several other reactions occur Inside the cake temperatures will not be higher than 100 °C
when certain temperatures are reached. For example, as long as water is present in the cake. Using an average
Dussy et al. (2005), were only able to convert a maximum baking time of 45 min, the timepoints of the Veress et al.
of 70% THCA into THC. They mention polymerization (1990) study and the above assumption that their peaks
and oxidation of THCA and THC to CBN and CBNA, represent 100% decarboxylation, this would mean that
respectively, as side reactions. The THC degradation to CBN only 1/3 of the THCA is converted into THC. Coming back
can already be considerable at temperatures between 85 – to the currently used total THC calculations for its limits,
100 °C (Repka et al., 2006). Having these reactions, which mentioned at the beginning of this paper, this would
reduce the THC content in mind, it is interesting that the mean that instead of the actually present THC content in
THCA decarboxylation reaction starts at 90 °C (Veress et al., the heated hemp flour of ca. 33% (THC created through
1990; Peschel, 2010). THCA-decarboxylation) + ca. 10% (original THC content
in hemp flour) = ca. 43% (realistic THC content in heated
Implications of THCA decarboxylation to real live scenarios hemp flour), using the total THC measurement method
e.g. baking leads to an overestimation of 57%. These calculations are
One has to differentiate between the temperatures used only approximations, because the Veress study was carried
to heat the oven, the temperature reached on the outside out on heated glass plates and not with hemp flour cake
of the cake, which, for instance, has a proportion of hemp in a regular oven. Nonetheless, they give an impression to
flour in it, and the temperature inside. It is reasonable to what extent the total THC measurements overestimate
assume that relevant temperatures for THC-evaporation the actual THC content.
are reached (presuming oven temperatures with an average
of 180 °C) only on the outside of the cake. However, THCA
and THC degradation will already play a role.
2
Literature Repka, M. A., Munjal, M., ElSohly, M. A., & Ross, S.
A. (2006). Temperature stability and bioadhesive
Dussy, F. E., Hamberg, C., Luginbühl, M., Schwerzmann, properties of Δ9-tetrahydrocannabinol incorporated
T., & Briellmann, T. A. (2005). Isolation of Δ 9-THCA-A hydroxypropylcellulose polymer matrix systems. Drug
from hemp and analytical aspects concerning the development and industrial pharmacy, 32(1), 21-32.
determination of Δ 9-THC in cannabis products. Forensic
science international, 149(1), 3-10. Taschwer, M., & Schmid, M. G. (2015). Determination of the
relative percentage distribution of THCA and Δ 9-THC
Eichler, M., Spinedi, L., Unfer-Grauwiler, S., Bodmer, M., in herbal cannabis seized in Austria–Impact of different
Surber, C., Luedi, M., & Drewe, J. (2012). Heat exposure of storage temperatures on stability. Forensic Science
Cannabis sativa extracts affects the pharmacokinetic and International, 254, 167-171.
metabolic profile in healthy male subjects. Planta medica,
78(07), 686-691. Veress, T., Szanto, J. I., & Leisztner, L. (1990). Determination
of cannabinoid acids by high-performance liquid
Perrotin-Brunel, H., Buijs, W., Van Spronsen, J., Van chromatography of their neutral derivatives formed by
Roosmalen, M. J., Peters, C. J., Verpoorte, R., & Witkamp, thermal decarboxylation: I. Study of the decarboxylation
G. J. (2011). Decarboxylation of Δ 9-tetrahydrocannabinol: process in open reactors. Journal of chromatography A,
Kinetics and molecular modeling. Journal of Molecular 520, 339-347.
Structure, 987(1), 67-73.
Whittle, B., Hill, C. A., Flockhart, I. R., Downs, D. V., Gibson,
Peschel, W. (2010) Quality control of traditional cannabis P., & Wheatley, G. W. (2008). U.S. Patent No. 7,344,736.
tinctures: pattern, markers and stability. doi:10.3797/ Washington, DC: U.S. Patent and Trademark Office.
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European Industrial Hemp Association (EIHA) paper on:

Decarboxylation of Tetrahydrocannabinolic acid (THCA)

Download this paper and further documents at: www.eiha.org

Motivation and Summary Results

Side reactions affecting THC levels

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