Comparison of phytocannabinoids

Cannabinoids (/kəˈnæbənɔɪdzˌ ˈkænəbənɔɪdz/) are compounds found in the cannabis plant or synthetic compounds that can interact with the endocannabinoid system.^[1]^[2] The most notable cannabinoid is the phytocannabinoid tetrahydrocannabinol (THC) (Delta-9-THC), the primary intoxicating compound in cannabis.^[3]^[4] Cannabidiol (CBD) is another major constituent of some cannabis plants.^[5] Conversion of CBD to THC can occur when CBD is heated to temperatures between 250–300 °C (480 to 570°F), potentially leading to its partial transformation into THC.^[6]

At least 113 distinct cannabinoids have been isolated from cannabis.^[7] This article gives comparative structures of some of the more common natural and synthetic cannabinoids, as well as showing structures of legally banned and sanctioned cannabinoids.

Structures

Cannabinoid	2D Structure	3D Structure
CBC
CBCV
CBD
CBDD
CBDH
CBDO
CBDP
CBDV
CBE
CBG
CBGV
CBL
CBN
CBND
CBTC
CBV
delta-8-THC
delta-10-THC
THC
THCC
THCB
THCH
THCP
THCV

Legality

Cannabinoid	Quasi-psychedelic	Drug precursor	Legal status
CBCA, CBC			Legal in most countries
CBCVA, CBCV
CBDA, CBD	No	THC^[6]	See Cannabidiol § Legal status
CBDD
CBDH
CBDO
CBDPA, CBDP
CBDVA, CBDV
CBEA, CBE
CBGA, CBG
CBGVA, CBGV
CBLA, CBL
CBNA, CBN
CBNDA, CBND
CBTA, CBT
CBVA, CBV
delta-8-THC	Yes		Legal in most countries
delta-10-THC	Yes		Legal in most countries
THCA, THC	Yes		UN Convention on Psychotropic Substances
THCB
THCCA, THCC
THCH	Yes		Legal in most countries
THCPA, THCP	Yes		Legal in most countries
THCVA, THCV

Thermal properties

Conversion temperatures

Cyclization reaction	Temperature
CBD → THC	250 °C (482 °F) to 300 °C (572 °F)^[6]

Decarboxylation temperatures

All cannabinoids listed here and their acids are found naturally in the plant to varying degrees.

Decarboxylation reaction	Temperature
CBCA → CBC
CBCVA → CBCV
CBDA → CBD
CBDPA → CBDP
CBDVA → CBDV
CBEA → CBE
CBGA → CBG
CBGVA → CBGV
CBLA → CBL
CBNA → CBN
CBNDA → CBND
CBTA → CBT
CBVA → CBV
THCA → THC	230 °F (110 °C) to 250 °F (121 °C)^[8]^[9]
THCCA → THCC
THCPA → THCP
THCVA → THCV

Upon heating, cannabinoid acids decarboxylate to give their psychoactive cannabinoid. For example, Delta-9-tetrahydrocannabinol (THC) is the main psychoactive compound found in cannabis and is responsible for the "high" feeling when consumed. However, cannabis does not naturally contain significant amounts of THC. Instead, tetrahydrocannabinolic acid (THCA) is found naturally in raw and live cannabis and is non-intoxicating. Over time, THCA slowly converts to THC through a process of decarboxylation over the course of roughly a year, but can be sped up with exposure to high temperatures. When heated under conditions of 110 °C, decarboxylation generally occurs in 30–45 minutes. The decarboxylated THCA (THC) is added to cannabis edibles, as THCA is not orally active. When consumed orally, the liver breaks down and metabolizes THC into the more potent 11-hydroxy-THC.

Vaporization temperatures

Dry-herb vaporizers can be used to inhale cannabis in its flower form. There are 483 identifiable chemical constituents known to exist in the cannabis plant, and at least 85 different cannabinoids have been isolated from the plant.^[10] The aromatic terpenoids begin to vaporize at 126.0 °C (258.8 °F), but the more bioactive tetrahydrocannabinol (THC), and other cannabinoids also found in cannabis (often legally sold as cannabinoid isolates) like cannabidiol (CBD), cannabichromene (CBC), cannabigerol (CBG), cannabinol (CBN), do not vaporize until near their respective boiling points.

The cannabinoids listed here are found in the plant but only in trace amounts. However, they have also been extracted and sold as isolates online. Third party certification may help ensure buyers to avoid synthetic cannabinoids.

Cannabinoid	Boiling point
CBC	220 °C (428 °F)^[11]
CBCV
CBD	160 °C (320 °F)-180 °C (356 °F)^[11]
CBDD	?
CBDO
CBDP
CBDV
CBE
CBG	185 °C (365 °F)^[12]
CBGV
CBL
CBN	185 °C (365 °F)^[11]
CBT
CBV
delta-8-THC	175 °C (347 °F)-178 °C (352 °F)^[11]
delta-10-THC	?
THC	157 °C (315 °F)^[11]
THCB
THCC
THCP
THCV	<220^[11]

Structural scheduling

Table of plant cannabinoids^[13]
Cannabigerol-type (CBG)
Cannabigerol (E)-CBG-C₅	Cannabigerol monomethyl ether (E)-CBGM-C₅ A	Cannabinerolic acid A (Z)-CBGA-C₅ A	Cannabigerovarin (E)-CBGV-C₃
Cannabigerolic acid A (E)-CBGA-C₅ A	Cannabigerolic acid A monomethyl ether (E)-CBGAM-C₅ A		Cannabigerovarinic acid A (E)-CBGVA-C₃ A
Cannabichromene-type (CBC)
(±)-Cannabichromene CBC-C₅	(±)-Cannabichromenic acid A CBCA-C₅ A	(±)-Cannabivarichromene, (±)-Cannabichromevarin CBCV-C₃	(±)-Cannabichromevarinic acid A CBCVA-C₃ A
Cannabidiol-type (CBD)
(−)-Cannabidiol CBD-C₅	Cannabidiol momomethyl ether CBDM-C₅	Cannabidiol-C₄ CBD-C₄	(−)-Cannabidivarin CBDV-C₃	Cannabidiorcol CBD-C₁
Cannabidiolic acid CBDA-C₅			Cannabidivarinic acid CBDVA-C₃
Cannabinodiol-type (CBND)
Cannabinodiol CBND-C₅	Cannabinodivarin CBND-C₃
Tetrahydrocannabinol-type (THC)
Δ⁹-Tetrahydrocannabinol Δ⁹-THC-C₅		Δ⁹-Tetrahydrocannabinol-C₄ Δ⁹-THC-C₄	Δ⁹-Tetrahydrocannabivarin Δ⁹-THCV-C₃	Δ⁹-Tetrahydrocannabiorcol Δ⁹-THCO-C₁
Δ⁹-Tetrahydro- cannabinolic acid A Δ⁹-THCA-C₅ A	Δ⁹-Tetrahydro- cannabinolic acid B Δ⁹-THCA-C₅ B	Δ⁹-Tetrahydro- cannabinolic acid-C₄ A and/or B Δ⁹-THCA-C₄ A and/or B	Δ⁹-Tetrahydro- cannabivarinic acid A Δ⁹-THCVA-C₃ A	Δ⁹-Tetrahydro- cannabiorcolic acid A and/or B Δ⁹-THCOA-C₁ A and/or B
(−)-Δ⁸-trans-(6aR,10aR)- Δ⁸-Tetrahydrocannabinol Δ⁸-THC-C₅	(−)-Δ⁸-trans-(6aR,10aR)- Tetrahydrocannabinolic acid A Δ⁸-THCA-C₅ A	(−)-(6aS,10aR)-Δ⁹- Tetrahydrocannabinol *(−)-cis-Δ⁹-THC-C₅*
Cannabinol-type (CBN)
Cannabinol CBN-C₅	Cannabinol-C₄ CBN-C₄	Cannabivarin CBN-C₃	Cannabinol-C₂ CBN-C₂	Cannabiorcol CBN-C₁
Cannabinolic acid A CBNA-C₅ A	Cannabinol methyl ether CBNM-C₅
Cannabitriol-type (CBT)
(−)-(9R,10R)-trans- Cannabitriol *(−)-trans-CBT-C₅*	(+)-(9S,10S)-Cannabitriol *(+)-trans-CBT-C₅*	(±)-(9R,10S/9S,10R)- Cannabitriol *(±)-cis-CBT-C₅*	(−)-(9R,10R)-trans- 10-O-Ethyl-cannabitriol *(−)-trans-CBT-OEt-C₅*	(±)-(9R,10R/9S,10S)- Cannabitriol-C₃ *(±)-trans-CBT-C₃*
8,9-Dihydroxy-Δ^6a(10a)- tetrahydrocannabinol 8,9-Di-OH-CBT-C₅	Cannabidiolic acid A cannabitriol ester CBDA-C₅ 9-OH-CBT-C₅ ester	(−)-(6aR,9S,10S,10aR)- 9,10-Dihydroxy- hexahydrocannabinol, Cannabiripsol Cannabiripsol-C₅	(−)-6a,7,10a-Trihydroxy- Δ⁹-tetrahydrocannabinol (−)-Cannabitetrol	10-Oxo-Δ^6a(10a)- tetrahydrocannabinol OTHC
Cannabielsoin-type (CBE)
(5aS,6S,9R,9aR)- Cannabielsoin CBE-C₅		(5aS,6S,9R,9aR)- C₃-Cannabielsoin CBE-C₃
(5aS,6S,9R,9aR)- Cannabielsoic acid A CBEA-C₅ A	(5aS,6S,9R,9aR)- Cannabielsoic acid B CBEA-C₅ B	(5aS,6S,9R,9aR)- C₃-Cannabielsoic acid B CBEA-C₃ B
Cannabiglendol-C₃ OH-iso-HHCV-C₃	Dehydrocannabifuran DCBF-C₅	Cannabifuran CBF-C₅
Isocannabinoids
(−)-Δ⁷-trans-(1R,3R,6R)- Isotetrahydrocannabinol	(±)-Δ⁷-1,2-cis- (1R,3R,6S/1S,3S,6R)- Isotetrahydro- cannabivarin	(−)-Δ⁷-trans-(1R,3R,6R)- Isotetrahydrocannabivarin
Cannabicyclol-type (CBL)
(±)-(1aS,3aR,8bR,8cR)- Cannabicyclol CBL-C₅	(±)-(1aS,3aR,8bR,8cR)- Cannabicyclolic acid A CBLA-C₅ A	(±)-(1aS,3aR,8bR,8cR)- Cannabicyclovarin CBLV-C₃
Cannabicitran-type (CBT)
Cannabicitran CBT-C₅
Cannabichromanone-type (CBCN)
Cannabichromanone CBCN-C₅	Cannabichromanone-C₃ CBCN-C₃	Cannabicoumaronone CBCON-C₅

References

^ Abyadeh M, Gupta V, Paulo JA, Gupta V, Chitranshi N, Godinez A, et al. (September 2021). "A Proteomic View of Cellular and Molecular Effects of Cannabis". Biomolecules. 11 (10): 1411–1428. doi:10.3390/biom11101411. PMC 8533448. PMID 34680044.
^ "Marijuana, also called: Cannabis, Ganja, Grass, Hash, Pot, Weed". Medline Plus. 3 July 2017.
^ Lambert DM, Fowler CJ (August 2005). "The endocannabinoid system: drug targets, lead compounds, and potential therapeutic applications". Journal of Medicinal Chemistry. 48 (16): 5059–5087. doi:10.1021/jm058183t. PMID 16078824.
^ Pertwee R, ed. (2005). Cannabinoids. Springer-Verlag. p. 2. ISBN 978-3-540-22565-2.
^ "Bulletin on Narcotics – 1962 Issue 3 – 004". UNODC (United Nations Office of Drugs and Crime). 1962-01-01. Retrieved 2014-01-15.
^ ^a ^b ^c Czégény Z, Nagy G, Babinszki B, Bajtel Á, Sebestyén Z, Kiss T, et al. (April 2021). "CBD, a precursor of THC in e-cigarettes". Scientific Reports. 11 (1): 8951. Bibcode:2021NatSR..11.8951C. doi:10.1038/s41598-021-88389-z. PMC 8076212. PMID 33903673.
^ Aizpurua-Olaizola O, Soydaner U, Öztürk E, Schibano D, Simsir Y, Navarro P, et al. (February 2016). "Evolution of the Cannabinoid and Terpene Content during the Growth of Cannabis sativa Plants from Different Chemotypes". Journal of Natural Products. 79 (2): 324–331. doi:10.1021/acs.jnatprod.5b00949. PMID 26836472.
^ Wang M, Wang YH, Avula B, Radwan MM, Wanas AS, van Antwerp J, et al. (1 December 2016). "Decarboxylation Study of Acidic Cannabinoids: A Novel Approach Using Ultra-High-Performance Supercritical Fluid Chromatography/Photodiode Array-Mass Spectrometry". Cannabis and Cannabinoid Research. 1 (1): 262–271. doi:10.1089/can.2016.0020. PMC 5549281. PMID 28861498.
^ Wang M, Wang YH, Avula B, Radwan MM, Wanas AS, van Antwerp J, et al. (2016). "Decarboxylation Study of Acidic Cannabinoids: A Novel Approach Using Ultra-High-Performance Supercritical Fluid Chromatography/Photodiode Array-Mass Spectrometry". Cannabis and Cannabinoid Research. 1 (1): 262–271. doi:10.1089/can.2016.0020. PMC 5549281. PMID 28861498.
^ El-Alfy AT, Ivey K, Robinson K, Ahmed S, Radwan M, Slade D, et al. (June 2010). "Antidepressant-like effect of delta9-tetrahydrocannabinol and other cannabinoids isolated from Cannabis sativa L". Pharmacology, Biochemistry, and Behavior. 95 (4): 434–442. doi:10.1016/j.pbb.2010.03.004. PMC 2866040. PMID 20332000.
^ ^a ^b ^c ^d ^e ^f "Phytocannabinoid Boiling Points" (PDF). projectcbd.org. Archived (PDF) from the original on 2019-04-08. Retrieved 20 August 2021.
^ "CompTox Chemicals Dashboard". comptox.epa.gov. Retrieved 10 April 2024.
^ "Table of Natural Cannabinoids" (PDF).

[1] Abyadeh M, Gupta V, Paulo JA, Gupta V, Chitranshi N, Godinez A, et al. (September 2021). "A Proteomic View of Cellular and Molecular Effects of Cannabis". Biomolecules. 11 (10): 1411–1428. doi:10.3390/biom11101411. PMC 8533448. PMID 34680044.

[2] "Marijuana, also called: Cannabis, Ganja, Grass, Hash, Pot, Weed". Medline Plus. 3 July 2017.

[lambert-3] Lambert DM, Fowler CJ (August 2005). "The endocannabinoid system: drug targets, lead compounds, and potential therapeutic applications". Journal of Medicinal Chemistry. 48 (16): 5059–5087. doi:10.1021/jm058183t. PMID 16078824.

[4] Pertwee R, ed. (2005). Cannabinoids. Springer-Verlag. p. 2. ISBN 978-3-540-22565-2.

[5] "Bulletin on Narcotics – 1962 Issue 3 – 004". UNODC (United Nations Office of Drugs and Crime). 1962-01-01. Retrieved 2014-01-15.

[Czégény_2021-6] Czégény Z, Nagy G, Babinszki B, Bajtel Á, Sebestyén Z, Kiss T, et al. (April 2021). "CBD, a precursor of THC in e-cigarettes". Scientific Reports. 11 (1): 8951. Bibcode:2021NatSR..11.8951C. doi:10.1038/s41598-021-88389-z. PMC 8076212. PMID 33903673.

[Aizpurua-Olaizola_2016-7] Aizpurua-Olaizola O, Soydaner U, Öztürk E, Schibano D, Simsir Y, Navarro P, et al. (February 2016). "Evolution of the Cannabinoid and Terpene Content during the Growth of Cannabis sativa Plants from Different Chemotypes". Journal of Natural Products. 79 (2): 324–331. doi:10.1021/acs.jnatprod.5b00949. PMID 26836472.

[8] Wang M, Wang YH, Avula B, Radwan MM, Wanas AS, van Antwerp J, et al. (1 December 2016). "Decarboxylation Study of Acidic Cannabinoids: A Novel Approach Using Ultra-High-Performance Supercritical Fluid Chromatography/Photodiode Array-Mass Spectrometry". Cannabis and Cannabinoid Research. 1 (1): 262–271. doi:10.1089/can.2016.0020. PMC 5549281. PMID 28861498.

[9] Wang M, Wang YH, Avula B, Radwan MM, Wanas AS, van Antwerp J, et al. (2016). "Decarboxylation Study of Acidic Cannabinoids: A Novel Approach Using Ultra-High-Performance Supercritical Fluid Chromatography/Photodiode Array-Mass Spectrometry". Cannabis and Cannabinoid Research. 1 (1): 262–271. doi:10.1089/can.2016.0020. PMC 5549281. PMID 28861498.

[10] El-Alfy AT, Ivey K, Robinson K, Ahmed S, Radwan M, Slade D, et al. (June 2010). "Antidepressant-like effect of delta9-tetrahydrocannabinol and other cannabinoids isolated from Cannabis sativa L". Pharmacology, Biochemistry, and Behavior. 95 (4): 434–442. doi:10.1016/j.pbb.2010.03.004. PMC 2866040. PMID 20332000.

[projectcbd-11] ^ ^a ^b ^c ^d ^e ^f "Phytocannabinoid Boiling Points" (PDF). projectcbd.org. Archived (PDF) from the original on 2019-04-08. Retrieved 20 August 2021.

[12] "CompTox Chemicals Dashboard". comptox.epa.gov. Retrieved 10 April 2024.

[13] "Table of Natural Cannabinoids" (PDF).

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