• Advertise
  • Contact Us
  • Write For Us
  • Our Team
Extraction Magazine
No Result
View All Result
  • Botanical Extraction
    • Cannabinoids
    • Psychedelics
    • Nutraceutical
    • Product Refinement
  • Industry News
    • Business
    • Sustainability
    • Safety & Compliance
    • Partners
  • Extraction Technology
    • Equipment
    • Methods
    • Solvents
    • DIY Extraction
    • Analytical Techniques
  • Medical Research
  • Glossary
  • Business Directory
  • Botanical Extraction
    • Cannabinoids
    • Psychedelics
    • Nutraceutical
    • Product Refinement
  • Industry News
    • Business
    • Sustainability
    • Safety & Compliance
    • Partners
  • Extraction Technology
    • Equipment
    • Methods
    • Solvents
    • DIY Extraction
    • Analytical Techniques
  • Medical Research
  • Glossary
  • Business Directory
No Result
View All Result
Extraction Magazine
No Result
View All Result
Home Industry News

Physicochemical Property Data in the Cannabis Industry

Lance Griffin by Lance Griffin
February 22, 2020
in Industry News
Physicochemical Property Data in the Cannabis Industry

Physicochemical properties relate how a chemical interacts with certain physical environments. Understanding physicochemical properties is vital in developing effective pharmaceutically active materials. [1] Cannabis producers must analyze physicochemical parameters to ensure efficacious, standardized, and safe products. Specifically, physicochemical data indicates human/environmental toxicity, bioavailability, metabolism, and other effects. [2]

Many types of analysis are available for physicochemical properties. In 2015, Australian researchers selected 13 physicochemical tests for 664 drugs of natural origin, pointing out “causal relationships between physicochemical properties of potential drug candidates and absorption, distribution, metabolism, excretion, and toxicity (ADMET) prediction models.” [3]

READ ALSO

Green Extraction Techniques and Smart Solvents for Bioactive Recovery

Cannabis Business In South America

Four of these tests comprise what is known as the Rule of Five (notice the multiples of 5); failing more than two of these tests indicates poor oral bioavailability:

  1. Molecular weight (MW): less than 500 Daltons
  2. H-bond donors (HBD): does not exceed 5 hydrogen bond donors
  3. H-bond acceptors (HBA): does not exceed 10 hydrogen bond acceptors
  4. Calculated logarithm of the octanol/water partition coefficient (cLogP): less than 5 [3]

The applicability of the Rule of Five is apparent for cannabis producers since bioavailability describes how much of an active substance (cannabinoids in this case) actually reach systemic circulation. Does tetrahydrocannabinol (THC) pass the Rule of Five? Let’s take a look:

  • MW = 314.5 g/mol (or Da)
  • HBD = 1
  • HBA = 2
  • cLogP = 5.648

Based on these four criteria, THC passes three. This test provides only a glimpse into the power of physicochemical data, though. The Australian researchers also tested [3]:

  1. Distribution coefficient (LogD7.4): measures lipophilicity at a pH of 7.4 (known as physiological pH); values higher than 3.5 are considered to have poor aqueous solubility. For reference, the logD7.4 of tetrahydrocannabinol (THC) has been recorded at 7.07. [4]
  2. Solubility (LogS7.4): directly measures aqueous solubility at physiological pH.
  3. Number of sp3 hybridized carbons/total carbon count (Fsp3): measures tetrahedral carbon atom fraction, a gauge of molecular complexity.
  4. Number of stereogenic carbon atoms (Chiral): measures the potential of the compound to assume asymmetric forms, or enantiomers; THC has two chiral carbon atoms and four enantiomers, although the “left-handed” (-)-trans-delta-9-tetrahydrocannabinol is the natural and common form.
  5. Rotatable bonds (RTB): a lower number of rotatable bonds is associated with improved oral bioavailability [7]; specifically, 10 or more reduces bioavailability. THC has four rotatable bonds.
  6. Ring count (RNG): number of rings in a molecule used as another metric of molecular complexity. A THC molecule contains two rings.
  7. Aromatic ring count (AROM): records aromatic and heteroaromatic rings; more than three aromatic rings indicates poor drug developability. [3,8] THC has one aromatic ring per molecule.
  8. Polar surface area (PSA): PSA measures polar atoms over total surface area. It indicates cellular permeation, including blood-brain barrier penetration; values exceeding 140 square angstroms (Å2) have low permeability. [7] THC has a PSA of 29.46 Å2. [4]
  9. Percent polar surface area (%PSA): reflects polar and non-polar properties. [3]

In 2017, Lewis et al [10] investigated some of the physicochemical properties in a medical cannabis extract sample from the Canadian market. They identified 22 unique MWs summarized in the graphic below.

The researchers then decarboxylated the sample and reported 16 MWs, noting that “signals corresponding to the molecular weights of 26 compounds were not found in the decarboxylated cannabis extract.”

This research reflects early attempts to characterize the complex physicochemical properties of cannabis, which undergoes significant changes depending on processing. The study authors concluded that such data is necessary to “facilitate the adoption of medical cannabis extract-based products by the wider medical community.” [10]

References

  1. Tietgen H, Walden M. “Physicochemical Properties.” Drug Discovery and Evaluation: Safety and Pharmacokinetic Assays, edited by Vogel H.G., Maas J., Hock F.J., Mayer D., Springer, 2013, pp 1125-1138. Times Cited = 2 (Crossref)
  2. National Research Council. “Physicochemical Properties and Environmental Fate.” A Framework to Guide Selection of Chemical Alternatives, Washington (DC), National Academies Press (US), 2014.
  3. Camp D, et al. “Analysis of Physicochemical Properties for Drugs of Natural Origin.” Journal of Natural Products, vo.78, no.6, 2015, pp.1370-82. Journal Impact Factor = 4.257, Times Cited = 23
  4. Adelli GR, et al. “Effects of Specific Natural and Synthetic Cannabinoids.” Handbook of Cannabis and Related Pathologies: Biology, Pharmacology, Diagnosis, and Treatment, edited by V.R. Preedy, Academic Press, 2017.
  5. Böttcher “An Additive Definition of Molecular Complexity.” J Chem Inf Model, vol.56, no.3, pp.462-470. Journal Impact Factor = 3.966, Times Cited = 21 (ResearchGate)
  6. Hann M, et al. “Molecular Complexity and Its Impact on the Probability of Finding Leads for Drug Discovery.” J Chem Inf Comput Sci, vol.41, no.3, 2001, pp.856-64. Journal Impact Factor = 3.966, Times Cited = 717 (ResearchGate)
  7. Veber DF, et al. “Molecular Properties That Influence the Oral Bioavailability of Drug Candidates.” J Med Chem, vol.45, no.12, 2002, pp.2615-23. Journal Impact Factor = 6.054, Times Cited = 2,623 (ResearchGate)
  8. Ritchie TJ, Macdonald SJ. “The Impact of Aromatic Ring Count on Compound Developability–Are Too Many Aromatic Rings a Liability in Drug Design?” Drug Discov Today, vol.14, no.21-22, pp.1011-20. Journal Impact Factor = 6.369, Times Cited = 329 (ResearchGate)
  9. Pajouhesh H, Lenz GR. “Medicinal Chemical Properties of Successful Central Nervous System Drugs.” NeuroRx, vol.2, no.4, 2005, pp.541-553. Journal Impact Factor = N/A, Times Cited = 551 (ResearchGate)
  10. Lewis MM, et al. “Chemical Profiling of Medical Cannabis Extracts.” ACS Omega, vol.2, no.9, 2017, pp.6091-6103. Journal Impact Factor = 2.58, Times Cited = 11 (ResearchGate)

Related Posts

Green Extraction Techniques
Sustainability

Green Extraction Techniques and Smart Solvents for Bioactive Recovery

January 10, 2025
A vision for the cannabis business
Business

Cannabis Business In South America

September 16, 2024
Journey of Cannabis in America
Business

From Prohibition to Progress: The Oscillating Journey of Cannabis in America

September 13, 2024
Social Clubs in Spain
Business

Cannabis Social Clubs in Spain vs CoffeeShops in the Netherlands

August 23, 2024
Cannabis Industry Sector
Business

Latest News From The Cannabis Industry Sector

August 16, 2024
Cannabis in Asia
Business

Cannabis in Asia – Overview of Asian Laws

August 9, 2024
Next Post
The History of Distillation, Fraction 1

The History of Distillation, Fraction 1

LATEST ARTICLES

Green Extraction Techniques

Green Extraction Techniques and Smart Solvents for Bioactive Recovery

January 10, 2025
Wide angle view at two workers wearing protective suits while inspecting production at modern chemical plant, copy space

Collaborative Approaches in Botanical Extraction: Bridging Science and Industry

January 7, 2025
Areca Catechu

Inside the Betel Nut High: Exploring the Mind-Bending Effects of Areca Catechu

January 1, 2025
The Art of Extraction: Unlocking Nature’s Fragile Secrets

The Art of Extraction: Unlocking Nature’s Fragile Secrets

December 27, 2024

Subscribe Now

Subscribe to our newsletter now to receive quick updates from us



    Background
    About

    Extraction Magazine is the trusted provider of botanical extraction news, ever-changing politics, cool gadgets and technologies, and methods for producing safe, ethical, and compliant formulations.

    Advertisers
    Navigation
    • Botanical Extraction
    • Industry News
    • Extraction Technology
    • Medical Research
    • Glossary
    • Business Directory
    Recent Posts
    • Green Extraction Techniques and Smart Solvents for Bioactive Recovery
    • Collaborative Approaches in Botanical Extraction: Bridging Science and Industry
    • Inside the Betel Nut High: Exploring the Mind-Bending Effects of Areca Catechu
    • The Art of Extraction: Unlocking Nature’s Fragile Secrets
    Subscribe to our Newsletter
    loader

    Sitemap

    © 2025 Extraction Magazine is the trusted provider of botanical extraction news and the leading media in the ever-changing extraction industry.

    No Result
    View All Result
    • Industry News
    • Botanical Extraction
    • Medical Research
    • Medical Research
    • Glossary
    • Our Team
    • Write For Us

    © 2023 Extraction Magazine is the trusted provider of botanical extraction news and the leading media in the ever-changing extraction industry.