Comparison of phytocannabinoids#Decarboxylation Conversion Temperatures
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Cannabinoids ({{IPAc-en|k|ə|ˈ|n|æ|b|ə|n|ɔɪ|d|z|,|_|ˈ|k|æ|n|ə|b|ə|n|ɔɪ|d|z}}) are compounds found in the cannabis plant or synthetic compounds that can interact with the endocannabinoid system.{{cite journal | vauthors = Abyadeh M, Gupta V, Paulo JA, Gupta V, Chitranshi N, Godinez A, Saks D, Hasan M, Amirkhani A, McKay M, Salekdeh GH, Haynes PA, Graham SL, Mirzaei M | title = A Proteomic View of Cellular and Molecular Effects of Cannabis | journal = Biomolecules | volume = 11 | issue = 10 | pages = 1411–1428 | date = September 2021 | pmid = 34680044 | pmc = 8533448 | doi = 10.3390/biom11101411 | doi-access = free }}{{cite web |title= Marijuana, also called: Cannabis, Ganja, Grass, Hash, Pot, Weed |url=https://medlineplus.gov/marijuana.html |website=Medline Plus |date=3 July 2017}} The most notable cannabinoid is the phytocannabinoid tetrahydrocannabinol (THC) (Delta-9-THC), the primary intoxicating(at too much dose) compound in cannabis.{{cite journal | vauthors = Lambert DM, Fowler CJ | title = The endocannabinoid system: drug targets, lead compounds, and potential therapeutic applications | journal = Journal of Medicinal Chemistry | volume = 48 | issue = 16 | pages = 5059–5087 | date = August 2005 | pmid = 16078824 | doi = 10.1021/jm058183t }}{{cite book|title=Cannabinoids |url=https://archive.org/details/cannabinoidshand00pert |url-access=limited | veditors = Pertwee R |publisher=Springer-Verlag |year=2005 |isbn=978-3-540-22565-2 |page=[https://archive.org/details/cannabinoidshand00pert/page/n11 2]}} Cannabidiol (CBD) is another major constituent of some cannabis plants.{{cite web|url=http://www.unodc.org/unodc/en/data-and-analysis/bulletin/bulletin_1962-01-01_3_page005.html |title=Bulletin on Narcotics – 1962 Issue 3 – 004 |publisher=UNODC (United Nations Office of Drugs and Crime) |date=1962-01-01 |access-date=2014-01-15}} 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.{{cite journal | vauthors = Czégény Z, Nagy G, Babinszki B, Bajtel Á, Sebestyén Z, Kiss T, Csupor-Löffler B, Tóth B, Csupor D | title = CBD, a precursor of THC in e-cigarettes | journal = Scientific Reports | volume = 11 | issue = 1 | pages = 8951 | date = April 2021 | pmid = 33903673 | pmc = 8076212 | doi = 10.1038/s41598-021-88389-z | bibcode = 2021NatSR..11.8951C }}
At least 113 distinct cannabinoids have been isolated from cannabis.{{cite journal | vauthors = Aizpurua-Olaizola O, Soydaner U, Öztürk E, Schibano D, Simsir Y, Navarro P, Etxebarria N, Usobiaga A | title = Evolution of the Cannabinoid and Terpene Content during the Growth of Cannabis sativa Plants from Different Chemotypes | journal = Journal of Natural Products | volume = 79 | issue = 2 | pages = 324–331 | date = February 2016 | pmid = 26836472 | doi = 10.1021/acs.jnatprod.5b00949 }} 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
| class="wikitable sortable" style="width: auto; text-align: center" |
| Cannabinoid
! 2D Structure ! 3D Structure |
|---|
| CBC
| 250px | 250px |
| CBCV
| 250px | 250px |
| CBD
| 250px | 250px |
| CBDD
| 250px | 250px |
| CBDH
| 250px | 250px |
| CBDO
| 250px | |
| CBDP
| 250px | 250px |
| CBDV
| 250px | 250px |
| CBE
| 250px | 250px |
| CBG
| 250px | 250px |
| CBGV
| 250px | 250px |
| CBL
| 250px | 250px |
| CBN
| 250px | 250px |
| CBND
| 250px | 250px |
| CBTC
| 250px | 250px |
| CBV
| 250px | 250px |
| delta-3-THC
| 250px | |
| delta-4-THC
| 250px | |
| delta-7-THC
| 250px | |
| delta-8-THC
| 250px | 250px |
| delta-10-THC
| 250px | 205px |
| delta-11-THC
| 250px | |
| THC
| 250px | 250px |
| THCC
| 250px | 250px |
| THCB
| 250px | 250px |
| THCH
| 250px | 250px |
| THCP
| 250px | 250px |
| THCV
| 250px | 250px |
Legality
| class="wikitable sortable" style="width: auto; text-align: center" |
| Cannabinoid
! Quasi-psychedelic ! Drug precursor ! Legal status |
|---|
| CBCA, CBC
| | | Legal in most countries |
| CBCVA, CBCV
| | | |
| CBDA, CBD
| No | See {{section link|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-3-THC
| Yes | | Legal in most countries |
| delta-4-THC
| Yes | | Legal in most countries |
| delta-7-THC
| Yes | | Legal in most countries |
| delta-8-THC
| Yes | | Legal in most countries |
| delta-10-THC
| Yes | | Legal in most countries |
| delta-11-THC
| Yes | | Legal in most countries |
| THCA, THC
| Yes | |
| THCB
| | | |
| THCCA, THCC
| | | |
| THCH
| Yes | | Legal in most countries |
| THCPA, THCP
| Yes | | Legal in most countries |
| THCVA, THCV
| | | |
Thermal properties
= Conversion temperatures =
{{main|Conversion of CBD to THC}}
| class="wikitable sortable" style="width: auto; text-align: center" |
| Cyclization reaction
! Temperature |
|---|
| CBD → THC
| {{convert|250|°C|°F}} to {{convert|300|°C|°F}}{{cite journal | vauthors = Czégény Z, Nagy G, Babinszki B, Bajtel Á, Sebestyén Z, Kiss T, Csupor-Löffler B, Tóth B, Csupor D | title = CBD, a precursor of THC in e-cigarettes | journal = Scientific Reports | volume = 11 | issue = 1 | pages = 8951 | date = April 2021 | pmid = 33903673 | pmc = 8076212 | doi = 10.1038/s41598-021-88389-z | bibcode = 2021NatSR..11.8951C }} |
= Decarboxylation temperatures =
All cannabinoids listed here and their acids are found naturally in the plant to varying degrees.
{{more citations needed|section|date=November 2021}}
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 =
{{more citations needed|section|date=November 2021}}
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.{{cite journal | vauthors = El-Alfy AT, Ivey K, Robinson K, Ahmed S, Radwan M, Slade D, Khan I, ElSohly M, Ross S | title = Antidepressant-like effect of delta9-tetrahydrocannabinol and other cannabinoids isolated from Cannabis sativa L | journal = Pharmacology, Biochemistry, and Behavior | volume = 95 | issue = 4 | pages = 434–442 | date = June 2010 | pmid = 20332000 | pmc = 2866040 | doi = 10.1016/j.pbb.2010.03.004 }} The aromatic terpenoids begin to vaporize at {{convert|126.0|°C|°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.
| class="wikitable sortable" style="width: auto; text-align: center" |
| Cannabinoid
! Boiling point |
|---|
| CBC |
| CBCV
| |
| CBD |
| CBDD
| ? |
| CBDO
| |
| CBDP
| |
| CBDV
| |
| CBE
| |
| CBG
| {{Convert|185|C|F}}{{Cite web|url=https://comptox.epa.gov/dashboard/chemical/properties/DTXSID701014168|title=CompTox Chemicals Dashboard|website=comptox.epa.gov|access-date=10 April 2024}} |
| CBGV
| |
| CBL
| |
| CBN |
| CBT
| |
| CBV
| |
| delta-3-THC
| ? |
| delta-4-THC
| ? |
| delta-7-THC
| ? |
| delta-8-THC |
| delta-10-THC
| ? |
| delta-11-THC
| ? |
| THC |
| THCB
| |
| THCC
| |
| THCP
| |
| THCV |
Structural scheduling
{{see also|Structural scheduling of synthetic cannabinoids}}
| class="wikitable mw-collapsible mw-expanded" style="font-size:smaller; width:100%"
|+ Table of plant cannabinoids{{cite web |url=https://leg.mt.gov/content/Committees/Interim/2009_2010/Children_Family/Emerging-Issue/mmga-presentation-cannabinoid-table-aug2010.pdf |title=Table of Natural Cannabinoids}} |
|
! colspan="5" | Cannabigerol-type (CBG) |
| File:cannabigerol.png
Cannabigerol | File:cannabigerol monomethyl ether.png Cannabigerol | File:cannabinerolic acid A.png Cannabinerolic acid A Cannabigerovarin | |
| File:cannabigerolic acid A.png
Cannabigerolic acid A | File:cannabigerolic acid A monomethyl ether.png Cannabigerolic acid A | | File:cannabigerovarinic acid A.png Cannabigerovarinic acid A | |
|
! colspan="5" | Cannabichromene-type (CBC) |
| File:cannabichromene.png
(±)-Cannabichromene | File:cannabichromenic acid A.png (±)-Cannabichromenic acid A | File:cannabichromevarine.png (±)-Cannabivarichromene, (±)-Cannabichromevarin | File:cannabichromevarinic acid A.png (±)-Cannabichromevarinic | |
|
! colspan="5" | Cannabidiol-type (CBD) |
| File:cannabidiol.png
(−)-Cannabidiol | File:cannabidiol momomethyl ether.png Cannabidiol Cannabidiol-C4 (−)-Cannabidivarin Cannabidiorcol |
| File:cannabidiolic acid.png
Cannabidiolic acid | | | File:cannabidivarinic acid.png Cannabidivarinic acid | |
|
! colspan="5" | Cannabinodiol-type (CBND) |
| File:cannabinodiol.png
Cannabinodiol Cannabinodivarin | | | |
|
! colspan="5" | Tetrahydrocannabinol-type (THC) |
| File:THC.svg
Δ9-Tetrahydrocannabinol | | File:delta-9-tetrahydrocannabinol-C4.png Δ9-Tetrahydrocannabinol-C4 | File:delta-9-tetrahydrocannabivarin.png Δ9-Tetrahydrocannabivarin | File:tetrahydrocannabiorcol.png Δ9-Tetrahydrocannabiorcol |
| File:delta-9-tetrahydrocannabinolic acid A.png
Δ9-Tetrahydro- | File:delta-9-tetrahydrocannabinolic acid B.png Δ9-Tetrahydro- | File:delta-9-tetrahydrocannabinolic acid-C4.png Δ9-Tetrahydro- | File:delta-9-tetrahydrocannabivarinic acid A.png Δ9-Tetrahydro- | File:delta-9-tetrahydrocannabiorcolic acid.png Δ9-Tetrahydro- |
| File:delta-8-tetrahydrocannabinol.png
(−)-Δ8-trans-(6aR,10aR)- | File:delta-8-tetrahydrocannabinolic acid A.png (−)-Δ8-trans-(6aR,10aR)- | File:cis-delta-9-tetrahydrocannabinol.png (−)-(6aS,10aR)-Δ9- | | |
|
! colspan="5" | Cannabinol-type (CBN) |
| File:cannabinol.png
Cannabinol Cannabinol-C4 Cannabivarin Cannabinol-C2 Cannabiorcol |
| File:cannabinolic acid A.png
Cannabinolic acid A | File:cannabinol methyl ether.png Cannabinol methyl ether | | | |
|
! colspan="5" | Cannabitriol-type (CBT) |
| File:(-)-trans-cannabitriol.png
(−)-(9R,10R)-trans- | File:(+)-trans-cannabitriol.png (+)-(9S,10S)-Cannabitriol (±)-(9R,10S/9S,10R)- | File:trans-cannabitriol ethyl ether.png (−)-(9R,10R)-trans- | File:trans-cannabitriol-C3.png (±)-(9R,10R/9S,10S)- |
| File:8,9-dihydroxy-delta-6a(10a)-tetrahydrocannabinol.png
8,9-Dihydroxy-Δ6a(10a)- | File:cannabidiolic acid A cannabitriol ester.png Cannabidiolic acid A (−)-(6aR,9S,10S,10aR)- (−)-6a,7,10a-Trihydroxy- | File:10-oxo-delta-6a(10a)-tetrahydrocannabinol.png 10-Oxo-Δ6a(10a)- |
|
! colspan="5" | Cannabielsoin-type (CBE) |
| File:cannabielsoin.png
(5aS,6S,9R,9aR)- | (5aS,6S,9R,9aR)- | | |
| File:cannabielsoic acid A.png
(5aS,6S,9R,9aR)- | File:cannabielsoic acid B.png (5aS,6S,9R,9aR)- | File:C3-cannabielsoic acid B.png (5aS,6S,9R,9aR)- | | |
| File:cannabiglendol-C3.png
Cannabiglendol-C3 | File:dehydrocannabifuran.png Dehydrocannabifuran Cannabifuran | | |
|
! colspan="5" | Isocannabinoids |
| File:delta-7-trans-isotetrahydrocannabinol.png
(−)-Δ7-trans-(1R,3R,6R)- | File:delta-7-cis-isotetrahydrocannabivarin.png (±)-Δ7-1,2-cis- | File:delta-7-trans-isotetrahydrocannabivarin.png (−)-Δ7-trans-(1R,3R,6R)- | | |
|
! colspan="5" | Cannabicyclol-type (CBL) |
| File:cannabicyclol.png
(±)-(1aS,3aR,8bR,8cR)- | File:cannabicyclolic acid A.png (±)-(1aS,3aR,8bR,8cR)- (±)-(1aS,3aR,8bR,8cR)- | | |
|
! colspan="5" | Cannabicitran-type (CBT) |
| File:cannabicitran.png
Cannabicitran | | | | |
|
! colspan="5" | Cannabichromanone-type (CBCN) |
| File:cannabichromanone.png
Cannabichromanone | File:cannabichromanone-C3.png Cannabichromanone-C3 Cannabicoumaronone | | |
References
{{Reflist}}
{{Cannabinoids}}