Template:Phytocannabinoids
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Phytocannabinoid ← phytocannabinoid acid
Quasi-psychedelic phytocannabinoids
- Δ-8-THC. Psychoactive, but about half as potent as Δ-9-THC.
- Decarboxylation: Δ-8-THCA → Δ-8-THC -- only trace amounts exist in cannabis
- Chemical conversion: CBD + acid 8 h → 50% Δ-8-THC
- Δ-9-THC (THC). Most abundant psychoactive component of cannabis. Is the standard when comparing THC analogs.
- Biosynthesis: Tetrahydrocannabinolic acid (THCA) synthase is an enzyme responsible for catalyzing the formation of THCA from cannabigerolic acid (CBGA). GMO yeast with a transgenic placement of a THCA synthase gene from Cannabis will produce THC
- Decarboxylation: THCA (more info) → THC -- The decarboxylation of this compound by heat is essential for the psychoactive effect of smoked cannabis, and depends on conversion of the enol to a keto group when the alpha carbon is protonated.
- Chemical conversion: CBD + acid 8 h → 50% THC
- Δ-10-THC. Psychoactive, but less potent than Δ-8-THC.
- Decarboxylation: Δ-10-THCA → Δ-10-THC-- only trace amounts exist in cannabis
- Chemical conversion: CBD + acid
- Δ-11-THC. Psychoactive, but little is known about this compound.
- THCB (more info)
- THCH (more info). 25 times more potent than THC.
- Decarboxylation: THCHA → THCH -- only trace amounts exist in cannabis
- Chemical conversion: CBDH + acid
- THCP (more info). 30 times more potent than THC.
- Biosynthesis: CBGPA → THCPA → THCP[1]
- Decarboxylation: THCPA → THCP-- only trace amounts exist in cannabis
- Chemical conversion: CBDP + acid
Quasi-psychedelic phytocannabinoids synthesized through chemical modification
- HHC
- HHCH
- HHCP-O-acetate
- THC-O-acetate. 3-5 times more potent than THC.
- Metabolization: THCAO is a prodrug, meaning it requires metabolization in order to take effect. It metabolically undergoes an activation process of converting to THC through de-acetylation, then THC continues into its own primary metabolites similarly to THC's oral route. Because of this, the onset when smoked can be significantly longer ranging from 20-45 minutes, but not as long as ingesting THC orally in comparison. THCAO through the oral route can also have longer onsets than oral THC due to its extra metabolic processes, with an onset of around 90 minutes.[2]
- Decarboxylation: Lack of information on decarboxylation, but it can be inferred that it decarboxylates like its normal parent compound since research suggests that heating it at 340°C (644°F) unbinds the acetyl group, releasing toxic ketene gas.[3]
- Chemical conversion: acetic anhydride + Δ-9-THC/Δ-8-THC → Δ-9-THCAO/Δ-8-THCAO, respectively.[4]
- THCP-O-acetate
Non-quasi-psychedelic phytocannabinoids, some which can be synthesized to quasi-psychedelic cannabinoids with biosynthesis or chemical conversion (see above)
- CBC ← CBCA
- CBCV ← CBCVA
- CBD
- Biosynthesis: CBGA → CBDA → CBD[5]
- Decarboxylation: CBDA → CBD
- Chemical conversion: THC + iodine → CBD
- CBDD
- CBDV ← CBDVA
- CBDH
- CBDP
- Biosynthesis: CBGPA → CBDPA → CBDP[6]
- Decarboxylation: CBDPA → CBDP
- CBE ← CBEA
- CBG
- CBGM ← CBGAM
- CBGV ← CBGVA
- CBL ← CBLA
- CBLV ← CBLVA
- CBN ← CBNA
- CBT ← CBTA
- CBV ← CBVA
- THCC ← THCCA
- Despite sounding a lot like THC, THCC is more similar to CBD than it is to THC
- THCV ← THCVA
- THCV is non-psychoactive.[7]
- ↑ https://twitter.com/jefbev/status/1254137977933979648
- ↑ Cooke, Justin (25 January 2022). "How Are Cannabinoids Metabolized? (CBD, THC, CBG, THC-O, & More)". DailyCBD.
- ↑ https://pubs.acs.org/doi/10.1021/acs.chemrestox.2c00170
- ↑ https://www.erowid.org/library/books_online/future_synthetic/future_synthetic.shtml
- ↑ https://twitter.com/jefbev/status/1254137977933979648
- ↑ https://twitter.com/jefbev/status/1254137977933979648
- ↑ Abioye, A; Ayodele, O; Marinkovic, A; Patidar, R; Akinwekomi, A; Sanyaolu, A (31 January 2020). "Δ9-Tetrahydrocannabivarin (THCV): a commentary on potential therapeutic benefit for the management of obesity and diabetes". Journal of cannabis research. 2 (1): 6. doi:10.1186/s42238-020-0016-7. PMC 7819335
. PMID 33526143.