Wikipedia

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] At least 113 distinct cannabinoids have been isolated from cannabis.[6]

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 edit

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

Legality edit

Cannabinoid Legal status
CBCA, CBC Legal in most countries
CBCVA, CBCV
CBDA, CBD
CBDPA, CBDP
CBDVA, CBDV
CBEA, CBE
CBGA, CBG
CBGAM, CBGM
CBGVA, CBGV
CBLA, CBL
CBNA, CBN
CBNDA, CBND
CBTA, CBT
CBVA, CBV
THCA, THC UN Convention on Psychotropic Substances
THCCA, THCC
THCH Legal in most countries
THCPA, THCP Legal in most countries
THCVA, THCV

Thermal properties edit

Decarboxylation Conversion Temperatures edit

Heated cannabinoid Conversion temperature Resulting cannabinoid
THCa 230 °F (110 °C) to 250 °F (121 °C)[7] THC

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.

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
CBGAM → CBGM
CBGVA → CBGV
CBLA → CBL
CBNA → CBN
CBNDA → CBND
CBTA → CBT
CBVA → CBV
THCA → THC 110 °C (230 °F)[8]
THCCA → THCC
THCPA → THCP
THCVA → THCV

Vaporization temperatures edit

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.[9] 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)[10]
CBCV
CBD 160 °C (320 °F)-180 °C (356 °F)[10]
CBDP
CBDV
CBE
CBG 185 °C (365 °F)[11]
CBGM
CBGV
CBL
CBN 185 °C (365 °F)[10]
CBT
CBV
delta-8-THC 175 °C (347 °F)-178 °C (352 °F)[10]
THC 157 °C (315 °F)[10]
THCC
THCP
THCV <220[10]

Structural scheduling edit

See also: Structural scheduling of synthetic cannabinoids


Table of plant cannabinoids[12]
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-Δ6a(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-Δ6a(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 edit

  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.
  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.
  6. ^ 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.
  7. ^ Wang, Mei; Wang, Yan-Hong; Avula, Bharathi; Radwan, Mohamed M.; Wanas, Amira S.; Antwerp, John van; Patcher, John F.; ElSohly, Mahmoud A.; Khan, Ikhlas A. (1 December 2016). "Decarboxylation Study of Acidic Cannabinoids: A Novel Approach Using Ultra-High-Performance Supercritical Fluid Chromatography/Photodiode Array-Mass Spectrometry". Cannabis Cannabinoid Research. 1 (1): 262–271. doi:10.1089/can.2016.0020. PMC 5549281. PMID 28861498.
  8. ^ Wang, M; Wang, YH; Avula, B; Radwan, MM; Wanas, AS; van Antwerp, J; Parcher, JF; ElSohly, MA; Khan, IA (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. ^ El-Alfy; Abir T; et al. (Jun 2010). "Antidepressant-like effect of delta-9-tetrahydrocannabinol and other cannabinoids isolated from Cannabis sativa L". Pharmacology Biochemistry and Behavior. 95 (4): 434–42. doi:10.1016/j.pbb.2010.03.004. PMC 2866040. PMID 20332000.
  10. ^ 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.
  11. ^ "CompTox Chemicals Dashboard". comptox.epa.gov. Retrieved 10 April 2024.
  12. ^ "Table of Natural Cannabinoids" (PDF).
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