1. Beyond THC: Overlooked chemistry Hubert Marceau & Alexis St-Gelais, chemists Chemistry heavy presentation ;)

2. Beyond THC: Overlooked chemistry Phytochemia.com Who we are

3. Beyond THC: Overlooked chemistry Δ9-THCCBD Phytochemia.com

4. Beyond THC: Overlooked chemistry Δ9-THC CBD CBN CBGCBC And around 100 other reported cannabinoids Phytochemia.com

5. Beyond THC: Overlooked chemistry First: A quick review of the big guys Non-volatiles compounds: High molecular weight (more than 15 carbon atoms) High polarity Multiple metabolic origins Phytochemia.com

6. Beyond THC: Overlooked chemistry Cannflavin ACannflavin B Cannflavins (Flavonoids) PGE2 Inhibitor = Potential anti-Inflammatory Possible anthelmintic Phytochemia.com

7. Beyond THC: Overlooked chemistry Cannabisin (Lignanamide) Weak AChE Inhibitor = Potential aid against Alzeihmer Potential Anti-Aging Agent Cannabisin A (goes up to O) Phytochemia.com

8. Beyond THC: Overlooked chemistry Cannabisativine (Spermidine alkaloids) Unknown or no effects Cannabisativine Anhydrocannabisativine Phytochemia.com

9. Beyond THC: Overlooked chemistry Let’s talk about the small guys The volatile compounds: Low molecular weight (typically 9 to 15 carbon atoms) Low polarity Mostly the famous terpenes, sometimes also phenolics Phytochemia.com

10. Beyond THC: Overlooked chemistry α-Pinene Camphene β-Pinene Sabinene Δ3-Carene α-Phellandrene Myrcene α-Terpinene Limonene 1,8-Cineole γ-Terpinene cis-β-Ocimene trans-β-Ocimene α-Terpinolene β-Caryophyllene Around 200 other compounds reported in Cannabis Phytochemia.com

11. Beyond THC: Overlooked chemistry What are their use? For the plant: Protection from pests and herbivories Reproduction Defense against fungi, bacteria For us: Flavors and fragrances (spices, perfumes) Phytochemia.com

12. Beyond THC: Overlooked chemistry Volatiles analyzis Hollow capillary column High precision oven Detector(s) Phytochemia.com

13. Beyond THC: Overlooked chemistry What we get: chromatogram β-Phellandrene Myrcene α-Pinene trans-Sabinyl acetate (Example: Anthriscus sylvestris) Phytochemia.com

14. Beyond THC: Overlooked chemistry Common detectors A) Mass Spectrometer (MS) © Agilent Technologies Phytochemia.com

15. Beyond THC: Overlooked chemistry Drawbacks… γ-Cadinene β-Cubebene cis-Muurola-4(14),5-diene Spectral similarities Tedious data interpretation Phytochemia.com

16. Beyond THC: Overlooked chemistry Common detectors B) Flame Ionization Detection (FID) © Digi-Key Electronics More sensitive than MS (with exceptions) No structural identification →How can we identify compounds? Phytochemia.com

17. Beyond THC: Overlooked chemistry Option A: Standard Injection Allows absolute quantitation Not all compounds available as standards… Does not tell about whole fingerprint Peppermint Menthol ? ? ? ? ? ? ? Phytochemia.com

18. Beyond THC: Overlooked chemistry Option B: Dual-Column Screening Retention time Retention index 1030 1151 Phytochemia.com

19. Beyond THC: Overlooked chemistry Advantages of screening Phytochemia.com

20. Beyond THC: Overlooked chemistry Aromagram Each peak corresponds to a detected odor * = Characteristic odor Phytochemia.com Rice S, Koziel JA (2015 PLoS ONE 10(12): e0144160. doi:10.1371/journal.pone.0144160

21. Beyond THC: Overlooked chemistry Phytochemia.ca | 1 Rice S, Koziel JA (2015 PLoS ONE 10(12): e0144160. doi:10.1371/journal.pone.0144160 β-Pinene Alloaromadendrene Plus possible synergistic effects!

22. Beyond THC: Overlooked chemistry Example OrangeGrapefruit α-Pinene0.5%0.6% Sabinene0.3%0.5% β-Pinenetr Myrcene1.9% Octanal0.3%0.5% Limonene95.4%94.6% 1,8-Cineole0.3%0.2% Linalool0.3%0.1% Nonanal0.1% Citronellal0.1% Decanal0.3% Neraltr Geranial0.1% β-Caryophyllenetr0.2% Germacrene Dtr0.1% δ-Cadinenetr0.1% Nootkatone0.01%0.04% 99.59%99.66% Phytochemia.com Sinensals (<0.05%) Grapefruit mercaptan (<0.01%)

23. Beyond THC: Overlooked chemistry Currently… Phytochemia.com Research focused on illegal drug detection Potential to develop aroma-oriented strains Need for better knowledge of whole aromatic profile, including minoritary fragrant compounds

24. Beyond THC: Overlooked chemistry To summarize Phytochemia.com Plenty of non-cannabinoid compounds of interest in Cannabis Very limited knowledge of their true effects to date Very distinctive scent(s) of the plant could be much more exploited Need for broader research/characterization efforts