Learn about major cannabinoids

You can find information about cannabinoids elsewhere. The goal of this section is to provide basic info with a focus on structural differences and their impact on the HPLC analysis.

We will take Delta 9-THCA (THCA-A) as the basis for the discussion.

 

1. THCA-A – Delta-9-tetrahydrocannabinolic acid

Basic info: non-psychoactive (needs to be heated/decarbed to THC to be psychoactive); found as the acidic form in flower.

Red oxygen groups form weak bonds with both the mobile phase and the column packing resulting in retention in the column. Because of the acidic -COOH group, THCA-A analysis is highly dependent on the pH of the mobile phase. At low pH, it is in the acidic form (-COOH) and is retained well in C18 column – hence has a very long retention time. At high pH, it is in the form of basic acetate (-COO[-]) and is eluted immediately from the C18 column.

Medical benefits: does not bind to cannabinoid receptors and therefore does not display typical health benefits associated with cannabinoids. It is a precursor for potent THC. It was found to potentially have neuroprotective and anti-seizure properties

 

2. Delta 9-THC – Delta-9-tetrahydrocannabinol

Basic info: psychoactive, scheduled narcotic in most jurisdictions, not found in the fresh flower – it is formed by heating or curing of THCA-A found in flower. During this process, THCA-A loses -CO2 molecule – this process is called decarboxylation (loss of carboxylic group). Because the THC molecule doesn`t have the acidic -COOH, its analysis is not easily affected by pH.

Medical benefits: anticancer, anxiolytic (reduces anxiety), neuroprotective, antiemetic (helps with nausea), appetite stimulant

 

3. Delta 8-THC – Delta-8-tetrahydrocannabinol

Basic info: psychoactive; typically found in very small amounts in flower. It is usually prepared synthetically from CBD found in hemp. Delta-9 and Delta-8 molecules are practically identical, differentiating only in one bond – because of this, many columns and HPLC methods and labs are unable to distinguish these two compounds.

Medical benefits: analgesic, anti-inflammatory, treats asthma, antiemetic (helps with nausea), appetite stimulant

 

4. THCVA – Delta-9-Tetrahydrocannabivarinic acid

Basic info: non-psychoactive, found in small amounts in flower – there are flowers with genetics that give high concentrations of THCVA. When decarbed, it forms THCV. THCVA has a one-carbon shorter chain compared to THCA-A and therefore elutes faster from C18 column than THCA-A.

Medical benefits: as a precursor of THCV

 

5. THCV – delta-9-Tetrahydrocannabivarin

Basic info: psychoactive, formed by decarboxylation of THCVA. THCV is a Delta-9-THC analog with one carbon shorter side chain – as a result, elutes faster from C18 column compared to D9-THC.

Medical benefits: anti-convulsant (treatment of epilepsy), appetite suppressant (treatment of obesity), anti-oxidant (potential for delay of neurodegenerative diseases, such as Parkinson’s), promotes bone growth (osteoporosis treatment), schizophrenia treatment.

 

6. CBDA – Cannabidiolic acid

Basic info: non-psychoactive, found in hemp, legal in most jurisdictions. CBDA is a precursor to CBD. It differentiates from THCA-A by having an open ring in the structure. As in the case of THCA-A, mobile phase pH has a profound effect on its retention time.

Medical Benefits: Precursor to CBD 

7. CBD – Cannabidiol

Basic info: non-psychoactive, legal in most jurisdictions, formed by heating from CBDA, which causes decarboxylation (loss of CO2 molecule).

Medical benefits: treatment of chronic pain, inflammation, migraines, epilepsy, autoimmune diseases, depression, and anxiety

 

8. CBDV – Cannabidivarin

Basic info: non-psychoactive, legal in most jurisdictions, formed by decarboxylation of CBDVA. In a similar fashion to other “varin” analogs to phytocannabinoids, CBDV has a one-carbon shorter side chain compared to CBD.

Medical benefits: antiepileptic, treatment of autism, multiple sclerosis, intestinal inflammation

 

9. CBGA – Cannabigerolic acid

Basic info: non-psychoactive, CBGA is formed in the plant to trigger plant cell necrosis resulting in leaf pruning and better flower growth. CBGA has a side chain, which is closed to form other cannabinoids, such as THCA-A, CBDA, CBCA, hence CBGA is a precursor to phytocannabinoids. On its own, it is typically found in the grown plant only in small amounts.

Medical benefits:  helps diabetic patients combat cardiovascular disease, treatment of metabolic disorders, and colon cancer.

 

10. CBG – Cannabigerol

Basic info: non-psychoactive, decarboxylated version of CBGA

Medical benefits: treatment of glaucoma, cancer, Crohn`s disease, IBS

 

11. CBN – Cannabinol

Basic info: non-psychoactive, found in older plants as it is formed by oxydation of delta-9-THC due to exposure to air, heat, and light. It has an aromatic ring compared to THC. It can also be produced synthetically from CBD or CBG.

Medical benefits: antibacterial agent, neuroprotectant, appetite stimulant, anti-inflammatory (arthritis treatment)

 

12. CBC – Cannabichromene

Basic info: non-psychoactive, unable to form ring, made by decarboxylation of CBCA, which originates from CBGA. 

Medical benefits: anti-cancer, anti-inflammatory, inhibitor of acne, antidepressant

 

13. CBL – Cannabicyclol

Basic info: non-psychoactive, degradation product from CBC when exposed to UV light and oxidation. Usually found only in trace amounts.

Medical benefits: not studied

 

Biosynthesis of Phytocannabinoids – source: Cayman Chemicals

Attached is a poster from Cayman Chemicals with more detail on phytocannabinoid synthesis and nomenclature.