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Total Legal
A “Joint” Journey into the
Chemistry of Cannabinoids
Dr. Markus Roggen
• Who is Markus Roggen?
• What is Cannabis, Weed, Marijuana, the Devil’s Lettuce?
• Why Research; Fundamental and Applied?
From Leaf to Lab
• Imperial College (IC), London, UK
• M/Sci in chemistry, minors in mathematics and finance (Dr. Chris Braddock)
• Chemometrics & Sugars to Synthetic Building Blocks
• Federal Institute of Technology (ETH), Zürich, CH
• PhD in organic chemistry (Prof. Dr. Erick Carreira)
• Iridium-Catalyzed Allylic Substitution
• The Scripps Research Institute (TSRI), San Diego, USA
• Postdoc in physical organic chemistry (Prof. Dr. Donna Blackmond)
• Enantioselective Organocatalytic Selenylation
Academic Background
• CSO of analytical laboratory
• DaVinci Laboratory of California, San Luis Obispo, CA, USA
• Built an analytical testing laboratory from scratch, in an ever-changing cannabis
regulation environment
• VP of extraction and production operation
• OutCo, San Diego, CA, USA
• Built an extraction facility from scratch, R&D of methods and products
• Founder/CEO/CSO of R&D laboratory
• CBDV / Delic Labs / Controlled Chemistry, Vancouver, BC, Canada
• Cannabis R&D as CRO for international companies
• Built from scratch, sold to Delic, bought back assets, setting up again…
• Public-private partnership for cannabis research funding
Cannabis Industry Background
Research Genealogy
Sajni Shah
Kendra Payne
Dr. Tom Dupree
Dr. Eric Janusson
Dr. Duane Hean
Sean Ryan
Gursaanj Bajaj
Luiz Geraldo
Callum MacPhee
Klara Wyse
Bofeng Cheng
Rachel de Souza
Seth Hinz
Ziqing (Stella) Zhu
Katie O’Connell
Soheil Nasseri
Matthew Ke
Rehmanali Jiwani
Nat Juthaprachakul
Vanessa Clarke
Denys Dzuibii
Duo Lu
Wesley Sequeira
Hank Chen
Ali Wasti
Amanda Assen
Dingding Xuan
Tim Sun
Thomas Ford
Prof. Sammis
Prof. Reid
Prof. Huan
Prof. Kennepohl
Prof. Bizzoto
Brodie Thomson
Will Chappell
Joey Lai
Paul Foth
Isaiah O. Betinol
Pirouz Kiani
Weiying He
Alyssa Hui
UBC
CBDV/Delic
Markus Roggen
Imperial College
Dr. Chris Braddock
ETH Zürich
Prof. Erick Carreira
Scripps Research
Prof. Donna Blackmond
LinkedIn
Industry Genealogy
What is Cannabis
The plant kingdom's cheeky chemist
Cannabis History
1611
Jamestown
settlers bring
cannabis to
North America
1911
Massachusetts
becomes the
first state to
outlaw cannabis
1970s
Substance Control
Act classifies
Cannabis as
Schedule I
2000s
>7 million
arrests for
cannabis
possession in
USA
1996
California
legalize
medical
marijuana
2018
Canada
legalizes
recreational
cannabis
2018
USA Farm Bill
legalizes hemp
(<0.5%wt. THC)
1500 BC
Earliest written
reference to
medical
cannabis in
the Chinese
pharmacopeia
700 BC
Medical use of
cannabis in the
Middle East
recorded in the
Venidad
Cannabis Botany
• Originated in China
• Drug type makes cannabinoids
• Hemp makes fiber
Cannabis Business
• Sales are mixed, established markets are declining, new markets see
steady growth
• Many companies struggle to achieve profitability, large layoffs and
downsizing
• Industry is challenged by the illicit market and regulations
Size of Global Cannabis Industry: $51bil
Size of USA Cannabis Industry: $34bil
Year over Year Growth: 13%
Legal vs. Illicit (CAN): 33% illegal
Gaming cosmetics $50bil
YouTube Ad Rev. $29bil
YoY growth California: 3%
Illicit markets: 12% tobacco / 26% alcohol
Cannabis as Medicine
• Chronic pain and spasticity: moderate-quality evidence
• Nausea and vomiting due to chemotherapy: low-quality
• Sleep disorders: low-quality evidence
• Anti-cancer: no evidence
• Cancer-causing: no evidence
• Deadly overdose: no evidence
Time to intoxication:
• Inhalation: seconds to minutes
• Ingestion: 0.5 to 2 hours
DOI:10.1001/jama.2015.6358; DOI: 10.17226/24625
• Discovery of CBN in 1940 by Robert S. Cahn
• Isolation of CBD and THC in 1942 by Robert Adams
• Rediscovered & corrected in 1964 by Raphael Mechoulam
• Why did it take so long:
• Cannabinoids are not alkaloids!
Cannabis Chemistry
R. Adams, Bull. N. York Acad. Med. 1942, 18, 705–30.
Cannabis Biochemistry
• 1988 to 1993: Identification of cannabinoid binding sites CB1 and CB2
receptor
• CB1 found in brain, peripheral neurons, adipocytes, hepatocytes, etc.
• CB2 found in immune cells (B lymphocytes, macrophages)
DOI: 10.1016/j.cell.2016.10.004
Cannabis Biochemistry
• 1992 to 1997: Identification of anandamide and 2-AG as
neurotransmitters
• Work spearheaded by Mechoulam
Anandamide
From Sanskrit ”ananda” for Joy, Bliss
2-Arachidonoylglycerol
Present in relatively high levels
Cannabinoids
THC, ∆8, Decarboxylation
Cannabis Biochemistry
DOI: 10.1046/j.1432-1033.2001.02030.x
CBGA
THCA
CBDA
CBCA
Cannabis Chemistry
Dawson, D. & Roggen, M.
Recent Advances in the Science of Cannabis. 49–78 (2021)
Cannabis Chemistry
DOI: 10.1201/9780429274893
Cannabis Chemistry
OH
O
∆9-THCA-A
O
OH
OH
O
10a
10
8
7 6a
11
12
13
2
4
9
6
10b
1
3
5
Dibenzopyran numbering
1’ 3’ 5’
2’ 4’
OH
O
∆9-THC
Decarboxylation
heat, - CO2
OH
HO
CBD
Ring closure
acid
OH
O
∆8-THC
Isomerization
heat or acid
O
HO
Oxidation
base or ???
HU331
O
Cannabis Chemistry (Question Time!)
Cannabis Chemistry (Question Time!)
Cannabis Chemistry
DOI: 10.1021/acsomega.3c04496
• So many molecules
we should keep
track of
Why Research
Rapture’s Quadrant
like Pasteur’s Quadrant, but Pungent
Rapture’s Quadrant
Fundamental
Knowledge
Immediate Application
Applied
Fundamental
Applied
Research
Fundamental
Research
Tinkering
Framework spans curiosity-driven
to application-focused research
• Fundamental research without
immediate practical use
• Applied research for new
technologies, not fundamental
understanding
• Applied Fundamental:
Knowledge pursuit with specific
practical applications
Rapture’s Quadrant
Fundamental
Knowledge
Immediate Application
Framework spans curiosity-driven
to application-focused research
• Fundamental research without
immediate practical use
• Applied research for new
technologies, not fundamental
understanding
• Applied Fundamental:
Knowledge pursuit with specific
practical applications
Tinkering
Fundamental Research
Turning ‘Pot’ential into Publications
Why Is THCA Decarboxylation
Faster than CBDA? An in silico
Perspective.
He, W.; Foth, P. J.; Roggen, M.; Sammis, G. M.; Kennepohl, P.
https://doi.org/10.26434/chemrxiv.12909887.
Fundamental
Research
Decarboxylation Theory
• An integral step in cannabis production
• The plant produces cannabinoid acids
• The consumer wants neutral cannabinoids
THCA
Produced by plant
THC
Makes you high
Decarboxylation Observation (Question Time!)
Not all decarboxylations are equal
0
20
40
60
80
100
0 5 10 15 20 25 30 35 40 45
Decarb
%
Minutes
Decarboxylation at 110˚C
CBDA/CBD
THCA/THC
THCA THC
CBDA CBD
Computational Studies (Question Time!)
Steric vs. Electronic: Exploring the rate difference in THCA and CBDA
decarboxylation
Computational Studies
Computational Studies
Key Findings:
• Rate determining step is the
intermolecular protonation
• Rate difference is due to steric rather
than electronic effects
CBD Hydroxyquinone
Photo-Isomerises to a Highly
Reactive Intermediate.
Thomson, B.J., Hanna, S., Schwarzenberg, A., Kiani, P., Bizzotto, D.,
Kennepohl, P., Davies, A., Roggen, M., & Sammis, G.M.
(2023) Sci. Rep. 13, 6967.
Fundamental
Research
The Colour Purple
The Purple Problem
• CBD vape cartridges turn purple
• Reddit knows, peer reviewed does not
• Beam Test identifies cannabis (presence of CBD or CBG)
• Beam, W. Fourth Report of Wellcome Tropical Research
Laboratories, part B. Khartoum, 1911; pp 25
• DOI: 10.1016/0040-4020(68)88159-1
Purple Colour
When and Why does CBD turn purple?
CBD degrades 20% in 30 days at 37°C
15% CBD degradation in 30 days
Stabile CBD storage at pH 4-6
Light
Heat
Acid / Base
DOI: 10.1038/s41598-020-60477-6; DOI: 10.1089/can.2021.0004 36
Isolation of HU-331 and its Anion
Hexane
Water
Isolation of HU-331 and its Anion
1H NMR (300 MHz, DMSO-d6)
1H NMR (300 MHz, DMSO-d6)
Computational Investigation of Absorption
• TD-DFT-calculations of visible light
absorption of HU-331 and its anion
• Why are there anions in neutral solutions?
Computational Investigation of Absorption
𝝅𝑻
𝒏𝑶𝟒



40%
15%
35%
𝝅𝑯𝑩𝒒𝟑
𝝅𝑯𝑩𝒒𝟒
H+



𝝅𝑻
𝝅𝑯𝑩𝒒𝟑
95%
< 5%
𝝅𝑯𝑩𝒒𝟒
𝒏𝑶𝟐
Energy
HU-
331
HU-
331
Olivetol-HQ
anion
Forcing Purple
0
0.1
0.2
0.3
0.4
0.5
0.6
0.7
0.8
0.9
1
380 430 480 530 580 630 680
Absorbance
(A)
Wavelength (nm)
CBD
HU-331
HU-331 and CBD at 0.5 mg mL-1 in IPA. Λmax of HU-331, 413
nm.
448 nm light emission
• CBD has HU331 impurities
• Pure CBD doesn’t turn purple
• Selectively irradiate HU331
• Complete HU331 degradation in 15min
The Fate of Purple
48 h
Everything is Possible!
• Photoexcitation of
hydroxyquinones
• Hydroxyquinol 5:
unstable in air
• 5 quickly degrades to
host of new quinones
• O2
- and H2O2 as by-
products, which start
more degradation
• What about toxicology?
• What are the pathways for other cannabinoids?
• Tobacco companies need more stability data!
Everything is Possible!
Applied Research
Inhale Data, Exhale Insights
Efficient Safety
Fast, Easy, and Reliable Monitoring of
THCA and CBDA Decarboxylation in
Cannabis Flower and Oil Samples
Using Infrared Spectroscopy
Shah, S., Wasti, A., Kozadjian, G., Cabral, J.-L., Wang, Y., & Roggen, M.
Agilent White Paper
Applied
Research
• Important in most cannabis processing
• There is no standard method
Decarboxylation Control
Before extraction
Biomass
After extraction
Oils
Problems with excessive heat:
• Instrument time
• High costs
• Side reactions and degradation
• Low yield
Don‘t Decarboxylate too Long
0
10
20
30
40
50
60
70
80
0
0.5
1
1.5
2
2.5
3
3.5
0 1000 2000 3000 4000 5000 6000
THC
THC
(%)
CBN
&
d8-THC
(%)
d8-THC
CBN
Elapsed Time (Minutes)
In-situ tracking via FTRI
50
Oil Decarb Ratio
THCA to THC
Y-axis: IR Prediction
X-axis: HPLC Concentration
Biomass Decarb Ratio
CBDA to CBD
• Small sample
• Fast and cheap
• Easy to use
Simulations of Test Reduction
Using Pooled Heavy Metals
Analysis in Cannabis.
Dupree, T.B., Assen, A.D., Janusson, E., Wise, A.R., Swider, J.M., & Roggen, M.
(2022) J. AOAC Int. 106, 484–489.
Applied
Research
The Problem of Compliant Testing
Heavy Metal Conundrum:
• Cannabis bioaccumulates heavy metals
• Extractor suffers from contaminated raw material
• Heavy metal testing is mandated
• Failed batches are expensive
• How to reduce product failure?
The Problem of Compliant Testing
Heavy Metal Conundrum:
• Late detection = loss / cross-contamination
• Test early / often = $$$
• How testing costs low for producers?
• And still make a profit as a testing lab?
Qualitative Pooled Testing
• How to test large number of people for a new virus?
• 133,816 patient samples / ~30,000 tests
• 20x more test for same budget
Quantitative Pooled Testing
DOI: 10.1097/QAI.0b013e3181ba37a7
• Pooling used to reduce costs of polymerase chain
reaction-based screening for acute HIV infection
• Variety of pooling strategies for prevalence of HIV
1% - 25%
Project Goals
• Save costs
• Increase product safety
• Reduce strain on the industry
• Increase sample throughput in cannabis testing labs
• Demonstrate that pooling strategies works
Pooled Testing of Heavy Metals!?
Herman Li
Dragonforce
Quantitative Pooled Testing
Indiv. Samples
• Value: 0-10
• Avg.: 1
• Fail: ≥5
• Fail: ~10%
• Tests: 25
Quantitative Pooled Testing: Minipool
Indiv. Samples
• Value: 0-10
• Avg.: 1
• Fail: ≥5
• Fail: ~10%
• Test whole
row
• If threshold
≥1.8, look for
failed sample
• Tests: 5
1.9
2.0
0.9
1.5
1.0
Quantitative Pooled Testing: Minipool
Indiv. Samples
• Value: 0-10
• Avg.: 1
• Fail: ≥5
• Fail: ~10%
• Test whole
row
• If threshold
≥1.8, look for
failed sample
• Tests: 5
n/a
1.4
0.9
1.5
1.0
Quantitative Pooled Testing: Minipool
Indiv. Samples
• Value: 0-10
• Avg.: 1
• Fail: ≥5
• Fail: 8%
• Test indiv.
samples of
failed row
until avg.
passes
• Tests: 11
• 56% saved
5.0
1.0 1.4 1.3 1.1 5.2
Quantitative Pooled Testing: Matrix
Indiv. Samples
• Value: 0-10
• Avg.: 1
• Fail: ≥5
• Fail: ~10%
1.9
2.0
0.9
1.5
1.0
2.1 1.8
1.3
0.8
1.4
• Test row &
column
• If threshold
≥1.8, look for
failed sample
• Tests: 10
1.5
1.1
Quantitative Pooled Testing: Matrix
Indiv. Samples
• Value: 0-10
• Avg.: 1
• Fail: ≥5
• Fail: 8%
2.2
0.9
1.5
1.0
1.8
1.3
0.8
1.4
• Test row &
column
• If threshold
≥1.8, look for
failed sample
• Tests: 12
• 52% saved
5.0
1.0
The Datasets: Only Flower
13% 20% 1.4%
Results
It depends:
• State
• Metals
• Pool strategy
• LOD
• LLOQ
Results
It depends:
• State
• Metals
• Pool strategy
• LOD
• LLOQ
Pooled Testing Conclusion
Outcomes
• 3 sample pool = 23.8% fewer tests (WA)
• 4 sample pool = 54.1% fewer tests (CA)
• Developed case-by-case to reduce time, effort, cost
What is Next for Cannabis Analysis?
DOI: 10.1186/s42238-021-00064-2
Reported %THC value from commerical laboratories
• THC %wt. is the only
important metric
• So much more
research potential
Applied Fundamental
High-Tech meets High Times
Extraction Yield Prediction for
the Large-Scale Recovery of
Cannabinoids.
Plommer, H., Betinol, I.O., Dupree, T., Roggen, M., & Reid, J.P.
(2024) Digit. Discov. 3 155-162.
Applied
Fundamental
Extracting Cannabis
• Cannabis companies are not doing well:
• Cumulative private-sector losses exceed C$16 bil.
• Operating cannabis extraction is costly
• Cannabis oil prices are falling
CAN
Cannabis
USA
Cannabis CPG Pharma
Avg. Cost
Margin
68% 51% 30% 26%
Extracting Cannabis
• Researched cannabis extraction since 2016
• Design of Experiment
• Solvent Kinetics and Thermodynamics
• Consulting for many producers
• Piecemeal solutions: slow, costly, not translatable
• How can extraction optimization be generalised?
• Unique extraction database
• Different instruments
• Variety of cultivars
• Various process conditions
• Yields of cannabinoids
• Amplifying a single large-scale experiment to predict outcomes of untested
conditions
Extracting Cannabis with Machine Learning
Random Forest ML
• Ensemble Learning Method
• Handles Various Data Types
• Feature Randomness
• Bagging Technique
• Automatic Feature
Selection
Extracting Cannabis with Machine Learning
Random Forest ML
• Ensemble Learning Method
• Handles Various Data Types
• Feature Randomness
• Bagging Technique
• Automatic Feature
Selection
Extracting Cannabis: AI + Manual Work
• Harmonizing information from different individual reports
• Multiple result types to increase information density
Extracting Cannabis: AI + Manual Work
• Harmonizing information from different individual reports
• Multiple result types to increase information density
• Brute force translation of producer data into database
• Cannabis extractions are also reactions: input ≠ output
AI for Extraction
• No extra experiments or costs
• Multi-Factor optimization solution
• Extraction Improvements
• Yield: +10%
• Throughput: +100%
• Quality: improved
• Waste: -50%
What is Next for Extraction AI?
• More data and systems
• LLM?
Summary
• Cannabis is a chaotic industry
One more thing…
The Perfect Joint
Does Size Matter for Performance? A
Study of How Particle Size Influences
Joint Smoking
Sun, T., Plommer, H., Shah, S., & Roggen, M. (2023)
Cann. Sci. Tech.
Applied
Fundamental
Pre-Rolls are Lighting Up
• Headset’s report on Pre-Rolls
• “Massive success”
Pre-Rolls are Lighting Up
• Headset’s report on Pre-Rolls
• “Massive success”
• 3rd in USA, 2nd in CAN
Kannabis
Aerosol
Research
Laboratory
© 2011-2023 by MJBiz, a division of Emerald X, LLC
Meet
Karl
Aerosol Sample Collection
• Using a Smoke Cycle Simulator
• Aerosols from three puffs collected on glass microfiber filters
• Volatile compounds, i.e. terpenes and toxicants caught in impinger
Quantitative Sample Analysis
• Full decarboxylation observed
• Smoke temperature: 44˚C
• THC b.p.: 157˚C at 0.05mmHg
• Myrcene b.p.: 167˚C at 1 atm
• Humulene b.p.: 106˚C at 5 mmHg
Experimental Setup
• Pre-Rolls various particle sizes (1- and 5-mm)
• Pre-rolls infused with kief and/or oil
• Analysis for cannabinoids and terpenes
0
10
20
30
40
50
60
70
First 1/3 Second 1/3 Third 1/3
THC
(mg/g)
THC by Puff Position
Inconsistent THC Delivery
• THC inhalation builds throughout consumption
• Highest delivery at end of a joint’s lifecycle
DOI: 10.1089/can.2023.0123
1/3 2/3 3/3
Effect of Particle Size on THC Delivery
• Fine grind: More THC per puff
• Coarse grind: More THC per Pre-Roll
• Highest delivery at end of a joint’s lifecycle
0
10
20
30
40
50
60
THC/puff (mg*20) THC/joint (mg) Puff count
THC 1-mm THC 5-mm
Infused: Same but Different
• Infused Pre-Rolls deliver
• More THC (~3x)
0
200
400
600
800
1000
1 g Regular Pre-
Rolls
1 g Kief Coated Pre-
Rolls
1 g Distillate
Infused Pre-Rolls
THC
(µg/mL)
THC per Pre-Roll
Infused: Same but Different
• Infused Pre-Rolls deliver
• More THC (~3x)
• But not on a per-puff basis!
0
1
2
3
4
5
6
7
1 g Regular Pre-Rolls 1 g Kief Coated Pre-
Rolls
1 g Distillate Infused
Pre-Rolls
THC
(µg/mL)
THC per Puff
Infused: Same but Different
Infused Pre-Rolls deliver
• More THC (~3x)
• More Terpenes (>4x)
• More flavor
• Different flavor
0
500
1000
1500
2000
2500
3000
3500
4000
4500
1 g Regular Pre-
Rolls
1 g Kief Coated
Pre-Rolls
1 g Distillate
Infused Pre-
Rolls
Terpenes
(µg)
Menthol
(+)-Valencene
α-Humulene
(-)-trans-Caryophyllene
Terpineol (mixture of isomers)
(1R)-endo-(+)-Fenchyl alcohol
(+)-Linalool
(R)-(+)-Limonene
β-myrcene
β-Pinene
Camphene
Sabinene
0
500
1000
1500
2000
2500
3000
3500
4000
4500
1 g Regular Pre-
Rolls
1 g Kief Coated
Pre-Rolls
1 g Distillate
Infused Pre-
Rolls
Terpenes
(µg)
Men
(+)-V
α-Hu
(-)-tr
Terp
(1R)-
(+)-L
(R)-(
β-my
β-Pin
Cam
Sabin
0
500
1000
1500
2000
2500
3000
3500
4000
4500
1 g Regular Pre-
Rolls
1 g Kief Coated
Pre-Rolls
1 g Distillate
Infused Pre-
Rolls
Terpenes
(µg)
0
500
1000
1500
2000
2500
3000
3500
4000
4500
1 g Regular Pre-
Rolls
1 g Kief Coated
Pre-Rolls
1 g Distillate
Infused Pre-
Rolls
Terpenes
(µg)
Menthol
(+)-Valencene
α-Humulene
(-)-trans-Caryophyl
Terpineol (mixture
(1R)-endo-(+)-Fenc
(+)-Linalool
(R)-(+)-Limonene
β-myrcene
β-Pinene
Camphene
Sabinene
0
100
200
300
400
500
600
700
800
900
1000
1 g Regular Pre-Rolls 1 g Kief Coated Pre-
Rolls
1 g Distillate Infused
Pre-Rolls
Toxicants
(μg)
Average Toxicants by Test Group
Benzaldehyde
Phenol
Benzonitrile
Infused: Toxicants, Watch Out!
• Infused Pre-Rolls deliver
• More THC (~3x)
• More Terpenes (>4x)
• More flavor
• More Toxicants!!!
Want a Sequel to Our Smoky Saga?
• Real-life inhalation profile
• Spliffs: Mixing cannabis with tobacco is a potent mix!?
• Cultivation: Effects on cannabis smoke composition
• What about vape cartridges? And dabs?
Summary
• Cannabis is a chaotic industry
• Cannabis can, maybe, help medicinally
• Cannabis can do a lot, but we don’t know why
• There is a lot of chemistry left to discover and research
- Process analysis
- Reaction mechanism
- Decomposition of cannabinoids
- Chemistry of consumption
Cannabis Accolades are Different
Academic:
• Scholarship of the Swiss Chemical Industry
• German DAAD Scholarship
Cannabis:
• ElSohly Award by ACS
• 40 under 40 by Marijuana Venture
• The Cannabis Scientist Power List, three years running
Cannabis Accolades are Different
Academic:
• Scholarship of the Swiss Chemical Industry
• German DAAD Scholarship
Cannabis:
• 40 under 40 by Marijuana Venture
• ElSohly Award, ACS
• The Cannabis Scientist Power List, three years running
Cannabis Accolades are Different
Academic:
• Scholarship of the Swiss Chemical Industry
• German DAAD Scholarship
Cannabis:
• 40 under 40 by Marijuana Venture
• ElSohly Award, ACS
• The Cannabis Scientist Power List, three years running
Thank you very much!
Questions?
Dr. Markus Roggen
markus@complexbiotech.com

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Total Legal: A “Joint” Journey into the Chemistry of Cannabinoids

  • 1. Total Legal A “Joint” Journey into the Chemistry of Cannabinoids Dr. Markus Roggen
  • 2. • Who is Markus Roggen? • What is Cannabis, Weed, Marijuana, the Devil’s Lettuce? • Why Research; Fundamental and Applied? From Leaf to Lab
  • 3. • Imperial College (IC), London, UK • M/Sci in chemistry, minors in mathematics and finance (Dr. Chris Braddock) • Chemometrics & Sugars to Synthetic Building Blocks • Federal Institute of Technology (ETH), Zürich, CH • PhD in organic chemistry (Prof. Dr. Erick Carreira) • Iridium-Catalyzed Allylic Substitution • The Scripps Research Institute (TSRI), San Diego, USA • Postdoc in physical organic chemistry (Prof. Dr. Donna Blackmond) • Enantioselective Organocatalytic Selenylation Academic Background
  • 4. • CSO of analytical laboratory • DaVinci Laboratory of California, San Luis Obispo, CA, USA • Built an analytical testing laboratory from scratch, in an ever-changing cannabis regulation environment • VP of extraction and production operation • OutCo, San Diego, CA, USA • Built an extraction facility from scratch, R&D of methods and products • Founder/CEO/CSO of R&D laboratory • CBDV / Delic Labs / Controlled Chemistry, Vancouver, BC, Canada • Cannabis R&D as CRO for international companies • Built from scratch, sold to Delic, bought back assets, setting up again… • Public-private partnership for cannabis research funding Cannabis Industry Background
  • 5. Research Genealogy Sajni Shah Kendra Payne Dr. Tom Dupree Dr. Eric Janusson Dr. Duane Hean Sean Ryan Gursaanj Bajaj Luiz Geraldo Callum MacPhee Klara Wyse Bofeng Cheng Rachel de Souza Seth Hinz Ziqing (Stella) Zhu Katie O’Connell Soheil Nasseri Matthew Ke Rehmanali Jiwani Nat Juthaprachakul Vanessa Clarke Denys Dzuibii Duo Lu Wesley Sequeira Hank Chen Ali Wasti Amanda Assen Dingding Xuan Tim Sun Thomas Ford Prof. Sammis Prof. Reid Prof. Huan Prof. Kennepohl Prof. Bizzoto Brodie Thomson Will Chappell Joey Lai Paul Foth Isaiah O. Betinol Pirouz Kiani Weiying He Alyssa Hui UBC CBDV/Delic Markus Roggen Imperial College Dr. Chris Braddock ETH Zürich Prof. Erick Carreira Scripps Research Prof. Donna Blackmond LinkedIn
  • 7. What is Cannabis The plant kingdom's cheeky chemist
  • 8. Cannabis History 1611 Jamestown settlers bring cannabis to North America 1911 Massachusetts becomes the first state to outlaw cannabis 1970s Substance Control Act classifies Cannabis as Schedule I 2000s >7 million arrests for cannabis possession in USA 1996 California legalize medical marijuana 2018 Canada legalizes recreational cannabis 2018 USA Farm Bill legalizes hemp (<0.5%wt. THC) 1500 BC Earliest written reference to medical cannabis in the Chinese pharmacopeia 700 BC Medical use of cannabis in the Middle East recorded in the Venidad
  • 9. Cannabis Botany • Originated in China • Drug type makes cannabinoids • Hemp makes fiber
  • 10. Cannabis Business • Sales are mixed, established markets are declining, new markets see steady growth • Many companies struggle to achieve profitability, large layoffs and downsizing • Industry is challenged by the illicit market and regulations Size of Global Cannabis Industry: $51bil Size of USA Cannabis Industry: $34bil Year over Year Growth: 13% Legal vs. Illicit (CAN): 33% illegal Gaming cosmetics $50bil YouTube Ad Rev. $29bil YoY growth California: 3% Illicit markets: 12% tobacco / 26% alcohol
  • 11. Cannabis as Medicine • Chronic pain and spasticity: moderate-quality evidence • Nausea and vomiting due to chemotherapy: low-quality • Sleep disorders: low-quality evidence • Anti-cancer: no evidence • Cancer-causing: no evidence • Deadly overdose: no evidence Time to intoxication: • Inhalation: seconds to minutes • Ingestion: 0.5 to 2 hours DOI:10.1001/jama.2015.6358; DOI: 10.17226/24625
  • 12. • Discovery of CBN in 1940 by Robert S. Cahn • Isolation of CBD and THC in 1942 by Robert Adams • Rediscovered & corrected in 1964 by Raphael Mechoulam • Why did it take so long: • Cannabinoids are not alkaloids! Cannabis Chemistry R. Adams, Bull. N. York Acad. Med. 1942, 18, 705–30.
  • 13. Cannabis Biochemistry • 1988 to 1993: Identification of cannabinoid binding sites CB1 and CB2 receptor • CB1 found in brain, peripheral neurons, adipocytes, hepatocytes, etc. • CB2 found in immune cells (B lymphocytes, macrophages) DOI: 10.1016/j.cell.2016.10.004
  • 14. Cannabis Biochemistry • 1992 to 1997: Identification of anandamide and 2-AG as neurotransmitters • Work spearheaded by Mechoulam Anandamide From Sanskrit ”ananda” for Joy, Bliss 2-Arachidonoylglycerol Present in relatively high levels
  • 17. Cannabis Chemistry Dawson, D. & Roggen, M. Recent Advances in the Science of Cannabis. 49–78 (2021)
  • 19. Cannabis Chemistry OH O ∆9-THCA-A O OH OH O 10a 10 8 7 6a 11 12 13 2 4 9 6 10b 1 3 5 Dibenzopyran numbering 1’ 3’ 5’ 2’ 4’ OH O ∆9-THC Decarboxylation heat, - CO2 OH HO CBD Ring closure acid OH O ∆8-THC Isomerization heat or acid O HO Oxidation base or ??? HU331 O
  • 22. Cannabis Chemistry DOI: 10.1021/acsomega.3c04496 • So many molecules we should keep track of
  • 23. Why Research Rapture’s Quadrant like Pasteur’s Quadrant, but Pungent
  • 24. Rapture’s Quadrant Fundamental Knowledge Immediate Application Applied Fundamental Applied Research Fundamental Research Tinkering Framework spans curiosity-driven to application-focused research • Fundamental research without immediate practical use • Applied research for new technologies, not fundamental understanding • Applied Fundamental: Knowledge pursuit with specific practical applications
  • 25. Rapture’s Quadrant Fundamental Knowledge Immediate Application Framework spans curiosity-driven to application-focused research • Fundamental research without immediate practical use • Applied research for new technologies, not fundamental understanding • Applied Fundamental: Knowledge pursuit with specific practical applications Tinkering
  • 27. Why Is THCA Decarboxylation Faster than CBDA? An in silico Perspective. He, W.; Foth, P. J.; Roggen, M.; Sammis, G. M.; Kennepohl, P. https://doi.org/10.26434/chemrxiv.12909887. Fundamental Research
  • 28. Decarboxylation Theory • An integral step in cannabis production • The plant produces cannabinoid acids • The consumer wants neutral cannabinoids THCA Produced by plant THC Makes you high
  • 29. Decarboxylation Observation (Question Time!) Not all decarboxylations are equal 0 20 40 60 80 100 0 5 10 15 20 25 30 35 40 45 Decarb % Minutes Decarboxylation at 110˚C CBDA/CBD THCA/THC THCA THC CBDA CBD
  • 30. Computational Studies (Question Time!) Steric vs. Electronic: Exploring the rate difference in THCA and CBDA decarboxylation
  • 32. Computational Studies Key Findings: • Rate determining step is the intermolecular protonation • Rate difference is due to steric rather than electronic effects
  • 33. CBD Hydroxyquinone Photo-Isomerises to a Highly Reactive Intermediate. Thomson, B.J., Hanna, S., Schwarzenberg, A., Kiani, P., Bizzotto, D., Kennepohl, P., Davies, A., Roggen, M., & Sammis, G.M. (2023) Sci. Rep. 13, 6967. Fundamental Research
  • 35. The Purple Problem • CBD vape cartridges turn purple • Reddit knows, peer reviewed does not • Beam Test identifies cannabis (presence of CBD or CBG) • Beam, W. Fourth Report of Wellcome Tropical Research Laboratories, part B. Khartoum, 1911; pp 25 • DOI: 10.1016/0040-4020(68)88159-1 Purple Colour
  • 36. When and Why does CBD turn purple? CBD degrades 20% in 30 days at 37°C 15% CBD degradation in 30 days Stabile CBD storage at pH 4-6 Light Heat Acid / Base DOI: 10.1038/s41598-020-60477-6; DOI: 10.1089/can.2021.0004 36
  • 37. Isolation of HU-331 and its Anion Hexane Water
  • 38. Isolation of HU-331 and its Anion 1H NMR (300 MHz, DMSO-d6) 1H NMR (300 MHz, DMSO-d6)
  • 39. Computational Investigation of Absorption • TD-DFT-calculations of visible light absorption of HU-331 and its anion • Why are there anions in neutral solutions?
  • 40. Computational Investigation of Absorption 𝝅𝑻 𝒏𝑶𝟒    40% 15% 35% 𝝅𝑯𝑩𝒒𝟑 𝝅𝑯𝑩𝒒𝟒 H+    𝝅𝑻 𝝅𝑯𝑩𝒒𝟑 95% < 5% 𝝅𝑯𝑩𝒒𝟒 𝒏𝑶𝟐 Energy HU- 331 HU- 331 Olivetol-HQ anion
  • 41. Forcing Purple 0 0.1 0.2 0.3 0.4 0.5 0.6 0.7 0.8 0.9 1 380 430 480 530 580 630 680 Absorbance (A) Wavelength (nm) CBD HU-331 HU-331 and CBD at 0.5 mg mL-1 in IPA. Λmax of HU-331, 413 nm. 448 nm light emission • CBD has HU331 impurities • Pure CBD doesn’t turn purple • Selectively irradiate HU331 • Complete HU331 degradation in 15min
  • 42. The Fate of Purple 48 h
  • 43. Everything is Possible! • Photoexcitation of hydroxyquinones • Hydroxyquinol 5: unstable in air • 5 quickly degrades to host of new quinones • O2 - and H2O2 as by- products, which start more degradation
  • 44. • What about toxicology? • What are the pathways for other cannabinoids? • Tobacco companies need more stability data! Everything is Possible!
  • 45. Applied Research Inhale Data, Exhale Insights
  • 47. Fast, Easy, and Reliable Monitoring of THCA and CBDA Decarboxylation in Cannabis Flower and Oil Samples Using Infrared Spectroscopy Shah, S., Wasti, A., Kozadjian, G., Cabral, J.-L., Wang, Y., & Roggen, M. Agilent White Paper Applied Research
  • 48. • Important in most cannabis processing • There is no standard method Decarboxylation Control Before extraction Biomass After extraction Oils
  • 49. Problems with excessive heat: • Instrument time • High costs • Side reactions and degradation • Low yield Don‘t Decarboxylate too Long 0 10 20 30 40 50 60 70 80 0 0.5 1 1.5 2 2.5 3 3.5 0 1000 2000 3000 4000 5000 6000 THC THC (%) CBN & d8-THC (%) d8-THC CBN Elapsed Time (Minutes)
  • 50. In-situ tracking via FTRI 50 Oil Decarb Ratio THCA to THC Y-axis: IR Prediction X-axis: HPLC Concentration Biomass Decarb Ratio CBDA to CBD • Small sample • Fast and cheap • Easy to use
  • 51. Simulations of Test Reduction Using Pooled Heavy Metals Analysis in Cannabis. Dupree, T.B., Assen, A.D., Janusson, E., Wise, A.R., Swider, J.M., & Roggen, M. (2022) J. AOAC Int. 106, 484–489. Applied Research
  • 52. The Problem of Compliant Testing Heavy Metal Conundrum: • Cannabis bioaccumulates heavy metals • Extractor suffers from contaminated raw material • Heavy metal testing is mandated • Failed batches are expensive • How to reduce product failure?
  • 53. The Problem of Compliant Testing Heavy Metal Conundrum: • Late detection = loss / cross-contamination • Test early / often = $$$ • How testing costs low for producers? • And still make a profit as a testing lab?
  • 54. Qualitative Pooled Testing • How to test large number of people for a new virus? • 133,816 patient samples / ~30,000 tests • 20x more test for same budget
  • 55. Quantitative Pooled Testing DOI: 10.1097/QAI.0b013e3181ba37a7 • Pooling used to reduce costs of polymerase chain reaction-based screening for acute HIV infection • Variety of pooling strategies for prevalence of HIV 1% - 25%
  • 56. Project Goals • Save costs • Increase product safety • Reduce strain on the industry • Increase sample throughput in cannabis testing labs • Demonstrate that pooling strategies works
  • 57. Pooled Testing of Heavy Metals!? Herman Li Dragonforce
  • 58. Quantitative Pooled Testing Indiv. Samples • Value: 0-10 • Avg.: 1 • Fail: ≥5 • Fail: ~10% • Tests: 25
  • 59. Quantitative Pooled Testing: Minipool Indiv. Samples • Value: 0-10 • Avg.: 1 • Fail: ≥5 • Fail: ~10% • Test whole row • If threshold ≥1.8, look for failed sample • Tests: 5
  • 60. 1.9 2.0 0.9 1.5 1.0 Quantitative Pooled Testing: Minipool Indiv. Samples • Value: 0-10 • Avg.: 1 • Fail: ≥5 • Fail: ~10% • Test whole row • If threshold ≥1.8, look for failed sample • Tests: 5
  • 61. n/a 1.4 0.9 1.5 1.0 Quantitative Pooled Testing: Minipool Indiv. Samples • Value: 0-10 • Avg.: 1 • Fail: ≥5 • Fail: 8% • Test indiv. samples of failed row until avg. passes • Tests: 11 • 56% saved 5.0 1.0 1.4 1.3 1.1 5.2
  • 62. Quantitative Pooled Testing: Matrix Indiv. Samples • Value: 0-10 • Avg.: 1 • Fail: ≥5 • Fail: ~10% 1.9 2.0 0.9 1.5 1.0 2.1 1.8 1.3 0.8 1.4 • Test row & column • If threshold ≥1.8, look for failed sample • Tests: 10
  • 63. 1.5 1.1 Quantitative Pooled Testing: Matrix Indiv. Samples • Value: 0-10 • Avg.: 1 • Fail: ≥5 • Fail: 8% 2.2 0.9 1.5 1.0 1.8 1.3 0.8 1.4 • Test row & column • If threshold ≥1.8, look for failed sample • Tests: 12 • 52% saved 5.0 1.0
  • 64. The Datasets: Only Flower 13% 20% 1.4%
  • 65. Results It depends: • State • Metals • Pool strategy • LOD • LLOQ
  • 66. Results It depends: • State • Metals • Pool strategy • LOD • LLOQ
  • 67. Pooled Testing Conclusion Outcomes • 3 sample pool = 23.8% fewer tests (WA) • 4 sample pool = 54.1% fewer tests (CA) • Developed case-by-case to reduce time, effort, cost
  • 68. What is Next for Cannabis Analysis? DOI: 10.1186/s42238-021-00064-2 Reported %THC value from commerical laboratories • THC %wt. is the only important metric • So much more research potential
  • 70. Extraction Yield Prediction for the Large-Scale Recovery of Cannabinoids. Plommer, H., Betinol, I.O., Dupree, T., Roggen, M., & Reid, J.P. (2024) Digit. Discov. 3 155-162. Applied Fundamental
  • 71. Extracting Cannabis • Cannabis companies are not doing well: • Cumulative private-sector losses exceed C$16 bil. • Operating cannabis extraction is costly • Cannabis oil prices are falling CAN Cannabis USA Cannabis CPG Pharma Avg. Cost Margin 68% 51% 30% 26%
  • 72. Extracting Cannabis • Researched cannabis extraction since 2016 • Design of Experiment • Solvent Kinetics and Thermodynamics • Consulting for many producers • Piecemeal solutions: slow, costly, not translatable • How can extraction optimization be generalised? • Unique extraction database • Different instruments • Variety of cultivars • Various process conditions • Yields of cannabinoids • Amplifying a single large-scale experiment to predict outcomes of untested conditions
  • 73. Extracting Cannabis with Machine Learning Random Forest ML • Ensemble Learning Method • Handles Various Data Types • Feature Randomness • Bagging Technique • Automatic Feature Selection
  • 74. Extracting Cannabis with Machine Learning Random Forest ML • Ensemble Learning Method • Handles Various Data Types • Feature Randomness • Bagging Technique • Automatic Feature Selection
  • 75. Extracting Cannabis: AI + Manual Work • Harmonizing information from different individual reports • Multiple result types to increase information density
  • 76. Extracting Cannabis: AI + Manual Work • Harmonizing information from different individual reports • Multiple result types to increase information density • Brute force translation of producer data into database • Cannabis extractions are also reactions: input ≠ output
  • 77. AI for Extraction • No extra experiments or costs • Multi-Factor optimization solution • Extraction Improvements • Yield: +10% • Throughput: +100% • Quality: improved • Waste: -50%
  • 78. What is Next for Extraction AI? • More data and systems • LLM?
  • 79. Summary • Cannabis is a chaotic industry
  • 80. One more thing… The Perfect Joint
  • 81. Does Size Matter for Performance? A Study of How Particle Size Influences Joint Smoking Sun, T., Plommer, H., Shah, S., & Roggen, M. (2023) Cann. Sci. Tech. Applied Fundamental
  • 82. Pre-Rolls are Lighting Up • Headset’s report on Pre-Rolls • “Massive success”
  • 83. Pre-Rolls are Lighting Up • Headset’s report on Pre-Rolls • “Massive success” • 3rd in USA, 2nd in CAN
  • 84. Kannabis Aerosol Research Laboratory © 2011-2023 by MJBiz, a division of Emerald X, LLC Meet Karl
  • 85. Aerosol Sample Collection • Using a Smoke Cycle Simulator • Aerosols from three puffs collected on glass microfiber filters • Volatile compounds, i.e. terpenes and toxicants caught in impinger
  • 86. Quantitative Sample Analysis • Full decarboxylation observed • Smoke temperature: 44˚C • THC b.p.: 157˚C at 0.05mmHg • Myrcene b.p.: 167˚C at 1 atm • Humulene b.p.: 106˚C at 5 mmHg
  • 87. Experimental Setup • Pre-Rolls various particle sizes (1- and 5-mm) • Pre-rolls infused with kief and/or oil • Analysis for cannabinoids and terpenes
  • 88. 0 10 20 30 40 50 60 70 First 1/3 Second 1/3 Third 1/3 THC (mg/g) THC by Puff Position Inconsistent THC Delivery • THC inhalation builds throughout consumption • Highest delivery at end of a joint’s lifecycle DOI: 10.1089/can.2023.0123 1/3 2/3 3/3
  • 89. Effect of Particle Size on THC Delivery • Fine grind: More THC per puff • Coarse grind: More THC per Pre-Roll • Highest delivery at end of a joint’s lifecycle 0 10 20 30 40 50 60 THC/puff (mg*20) THC/joint (mg) Puff count THC 1-mm THC 5-mm
  • 90. Infused: Same but Different • Infused Pre-Rolls deliver • More THC (~3x) 0 200 400 600 800 1000 1 g Regular Pre- Rolls 1 g Kief Coated Pre- Rolls 1 g Distillate Infused Pre-Rolls THC (µg/mL) THC per Pre-Roll
  • 91. Infused: Same but Different • Infused Pre-Rolls deliver • More THC (~3x) • But not on a per-puff basis! 0 1 2 3 4 5 6 7 1 g Regular Pre-Rolls 1 g Kief Coated Pre- Rolls 1 g Distillate Infused Pre-Rolls THC (µg/mL) THC per Puff
  • 92. Infused: Same but Different Infused Pre-Rolls deliver • More THC (~3x) • More Terpenes (>4x) • More flavor • Different flavor 0 500 1000 1500 2000 2500 3000 3500 4000 4500 1 g Regular Pre- Rolls 1 g Kief Coated Pre-Rolls 1 g Distillate Infused Pre- Rolls Terpenes (µg) Menthol (+)-Valencene α-Humulene (-)-trans-Caryophyllene Terpineol (mixture of isomers) (1R)-endo-(+)-Fenchyl alcohol (+)-Linalool (R)-(+)-Limonene β-myrcene β-Pinene Camphene Sabinene 0 500 1000 1500 2000 2500 3000 3500 4000 4500 1 g Regular Pre- Rolls 1 g Kief Coated Pre-Rolls 1 g Distillate Infused Pre- Rolls Terpenes (µg) Men (+)-V α-Hu (-)-tr Terp (1R)- (+)-L (R)-( β-my β-Pin Cam Sabin 0 500 1000 1500 2000 2500 3000 3500 4000 4500 1 g Regular Pre- Rolls 1 g Kief Coated Pre-Rolls 1 g Distillate Infused Pre- Rolls Terpenes (µg) 0 500 1000 1500 2000 2500 3000 3500 4000 4500 1 g Regular Pre- Rolls 1 g Kief Coated Pre-Rolls 1 g Distillate Infused Pre- Rolls Terpenes (µg) Menthol (+)-Valencene α-Humulene (-)-trans-Caryophyl Terpineol (mixture (1R)-endo-(+)-Fenc (+)-Linalool (R)-(+)-Limonene β-myrcene β-Pinene Camphene Sabinene
  • 93. 0 100 200 300 400 500 600 700 800 900 1000 1 g Regular Pre-Rolls 1 g Kief Coated Pre- Rolls 1 g Distillate Infused Pre-Rolls Toxicants (μg) Average Toxicants by Test Group Benzaldehyde Phenol Benzonitrile Infused: Toxicants, Watch Out! • Infused Pre-Rolls deliver • More THC (~3x) • More Terpenes (>4x) • More flavor • More Toxicants!!!
  • 94. Want a Sequel to Our Smoky Saga? • Real-life inhalation profile • Spliffs: Mixing cannabis with tobacco is a potent mix!? • Cultivation: Effects on cannabis smoke composition • What about vape cartridges? And dabs?
  • 95. Summary • Cannabis is a chaotic industry • Cannabis can, maybe, help medicinally • Cannabis can do a lot, but we don’t know why • There is a lot of chemistry left to discover and research - Process analysis - Reaction mechanism - Decomposition of cannabinoids - Chemistry of consumption
  • 96. Cannabis Accolades are Different Academic: • Scholarship of the Swiss Chemical Industry • German DAAD Scholarship Cannabis: • ElSohly Award by ACS • 40 under 40 by Marijuana Venture • The Cannabis Scientist Power List, three years running
  • 97. Cannabis Accolades are Different Academic: • Scholarship of the Swiss Chemical Industry • German DAAD Scholarship Cannabis: • 40 under 40 by Marijuana Venture • ElSohly Award, ACS • The Cannabis Scientist Power List, three years running
  • 98. Cannabis Accolades are Different Academic: • Scholarship of the Swiss Chemical Industry • German DAAD Scholarship Cannabis: • 40 under 40 by Marijuana Venture • ElSohly Award, ACS • The Cannabis Scientist Power List, three years running
  • 99. Thank you very much! Questions? Dr. Markus Roggen markus@complexbiotech.com