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

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

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

Decarboxylation Conversion Temperatures

Heated cannabinoid Conversion temperature Resulting cannabinoid
THCa 230 °F (110 °C) to 250 °F (121 °C)[7] THC
This section needs additional citations for verification. Please help improve this article by adding citations to reliable sources in this section. Unsourced material may be challenged and removed.Find sources: "Comparison of phytocannabinoids" – news · newspapers · books · scholar · JSTOR (November 2021) (Learn how and when to remove this template message)

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
CBCACBC
CBCVA → CBCV
CBDACBD
CBDPA → CBDP
CBDVA → CBDV
CBEA → CBE
CBGACBG
CBGAM → CBGM
CBGVA → CBGV
CBLA → CBL
CBNA → CBN
CBNDA → CBND
CBTA → CBT
CBVA → CBV
THCATHC 110 °C (230 °F)[8]
THCCA → THCC
THCPA → THCP
THCVA → THCV

Vaporization temperatures

This section needs additional citations for verification. Please help improve this article by adding citations to reliable sources in this section. Unsourced material may be challenged and removed.Find sources: "Comparison of phytocannabinoids" – news · newspapers · books · scholar · JSTOR (November 2021) (Learn how and when to remove this template message)

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 105 °C (221 °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

See also: Structural scheduling of synthetic cannabinoids


Table of plant cannabinoids[12]
Cannabigerol-type (CBG)
Chemical structure of cannabigerol.

Cannabigerol
(E)-CBG-C5

Chemical structure of cannabigerol monomethyl ether.

Cannabigerol
monomethyl ether
(E)-CBGM-C5 A

Chemical structure of cannabinerolic acid A.

Cannabinerolic acid A
(Z)-CBGA-C5 A

Chemical structure of cannabigerovarin.

Cannabigerovarin
(E)-CBGV-C3

Chemical structure of cannabigerolic acid A.

Cannabigerolic acid A
(E)-CBGA-C5 A

Chemical structure of cannabigerolic acid A monomethyl ether.

Cannabigerolic acid A
monomethyl ether
(E)-CBGAM-C5 A

Chemical structure of cannabigerovarinic acid A.

Cannabigerovarinic acid A
(E)-CBGVA-C3 A

Cannabichromene-type (CBC)
Chemical structure of cannabichromene.

(±)-Cannabichromene
CBC-C5

Chemical structure of cannabichromenic acid A.

(±)-Cannabichromenic acid A
CBCA-C5 A

Chemical structure of cannabichromevarin.

(±)-Cannabivarichromene, (±)-Cannabichromevarin
CBCV-C3

Chemical structure of cannabichromevarinic acid A.

(±)-Cannabichromevarinic
acid A
CBCVA-C3 A

Cannabidiol-type (CBD)
Chemical structure of cannabidiol.

(−)-Cannabidiol
CBD-C5

Chemical structure of cannabidiol momomethyl ether.

Cannabidiol
momomethyl ether
CBDM-C5

Chemical structure of cannabidiol-C4

Cannabidiol-C4
CBD-C4

Chemical structure of cannabidivarin.

(−)-Cannabidivarin
CBDV-C3

Chemical structure of cannabidiorcol.

Cannabidiorcol
CBD-C1

Chemical structure of cannabidiolic acid.

Cannabidiolic acid
CBDA-C5

Chemical structure of cannabidivarinic acid.

Cannabidivarinic acid
CBDVA-C3

Cannabinodiol-type (CBND)
Chemical structure of cannabinodiol.

Cannabinodiol
CBND-C5

Chemical structure of cannabinodivarin.

Cannabinodivarin
CBND-C3

Tetrahydrocannabinol-type (THC)
Chemical structure of Δ9-tetrahydrocannabinol.

Δ9-Tetrahydrocannabinol
Δ9-THC-C5

Chemical structure of Δ9-tetrahydrocannabinol-C4

Δ9-Tetrahydrocannabinol-C4
Δ9-THC-C4

Chemical structure of Δ9-tetrahydrocannabivarin.

Δ9-Tetrahydrocannabivarin
Δ9-THCV-C3

Chemical structure of tetrahydrocannabiorcol.

Δ9-Tetrahydrocannabiorcol
Δ9-THCO-C1

Chemical structure of Δ9-tetrahydrocannabinolic acid A.

Δ9-Tetrahydro-
cannabinolic acid A

Δ9-THCA-C5 A

Chemical structure of Δ9-tetrahydrocannabinolic acid B.

Δ9-Tetrahydro-
cannabinolic acid B
Δ9-THCA-C5 B

Chemical structure of Δ9-tetrahydrocannabinolic acid-C4

Δ9-Tetrahydro-
cannabinolic acid-C4
A and/or B
Δ9-THCA-C4 A and/or B

Chemical structure of Δ9-tetrahydrocannabivarinic acid A.

Δ9-Tetrahydro-
cannabivarinic acid A
Δ9-THCVA-C3 A

Chemical structure of Δ9-tetrahydrocannabiorcolic acid.

Δ9-Tetrahydro-
cannabiorcolic acid
A and/or B
Δ9-THCOA-C1 A and/or B

Chemical structure of Δ8-tetrahydrocannabinol.

(−)-Δ8-trans-(6aR,10aR)-
Δ8-Tetrahydrocannabinol
Δ8-THC-C5

Chemical structure of Δ8-tetrahydrocannabinolic acid A.

(−)-Δ8-trans-(6aR,10aR)-
Tetrahydrocannabinolic
acid A
Δ8-THCA-C5 A

Chemical structure of cis-Δ9tetrahydrocannabinol.

(−)-(6aS,10aR)-Δ9-
Tetrahydrocannabinol
(−)-cis9-THC-C5

Cannabinol-type (CBN)
Chemical structure of cannabinol.

Cannabinol
CBN-C5

Chemical structure of cannabinol-C4

Cannabinol-C4
CBN-C4

Chemical structure of cannabivarin.

Cannabivarin
CBN-C3

Chemical structure of cannabinol-C2

Cannabinol-C2
CBN-C2

Chemical structure of cannabiorcol.

Cannabiorcol
CBN-C1

Chemical structure of cannabinolic acid A.

Cannabinolic acid A
CBNA-C5 A

Chemical structure of cannabinol methyl ether.

Cannabinol methyl ether
CBNM-C5

Cannabitriol-type (CBT)
Chemical structure of (-)-trans-cannabitriol.

(−)-(9R,10R)-trans-
Cannabitriol
(−)-trans-CBT-C5

Chemical structure of (+)-trans-cannabitriol.

(+)-(9S,10S)-Cannabitriol
(+)-trans-CBT-C5

Chemical structure of cis-cannabitriol.

(±)-(9R,10S/9S,10R)-
Cannabitriol
(±)-cis-CBT-C5

Chemical structure of trans-cannabitriol ethyl ether.

(−)-(9R,10R)-trans-
10-O-Ethyl-cannabitriol
(−)-trans-CBT-OEt-C5

Chemical structure of trans-cannabitriol-C3

(±)-(9R,10R/9S,10S)-
Cannabitriol-C3
(±)-trans-CBT-C3

Chemical structure of 8,9-dihydroxy-Δ6a(10a)-tetrahydrocannabinol.

8,9-Dihydroxy-Δ6a(10a)-
tetrahydrocannabinol
8,9-Di-OH-CBT-C5

Chemical structure of cannabidiolic acid A cannabitriol ester.

Cannabidiolic acid A
cannabitriol ester
CBDA-C5 9-OH-CBT-C5 ester

Chemical structure of cannabiripsol.

(−)-(6aR,9S,10S,10aR)-
9,10-Dihydroxy-
hexahydrocannabinol,
Cannabiripsol
Cannabiripsol-C5

Chemical structure of cannabitetrol.

(−)-6a,7,10a-Trihydroxy-
Δ9-tetrahydrocannabinol
(−)-Cannabitetrol

Chemical structure of 10-oxo-Δ6a10a-tetrahydrocannabinol.

10-Oxo-Δ6a(10a)-
tetrahydrocannabinol
OTHC

Cannabielsoin-type (CBE)
Chemical structure of cannabielsoin.

(5aS,6S,9R,9aR)-
Cannabielsoin
CBE-C5

Chemical structure of C3-cannabielsoin.

(5aS,6S,9R,9aR)-
C3-Cannabielsoin
CBE-C3

Chemical structure of cannabielsoic acid A.

(5aS,6S,9R,9aR)-
Cannabielsoic acid A
CBEA-C5 A

Chemical structure of cannabielsoic acid B.

(5aS,6S,9R,9aR)-
Cannabielsoic acid B
CBEA-C5 B

Chemical structure of C3-cannabielsoic acid B.

(5aS,6S,9R,9aR)-
C3-Cannabielsoic acid B
CBEA-C3 B

Chemical structure of cannabiglendol-C3

Cannabiglendol-C3
OH-iso-HHCV-C3

Chemical structure of dehydrocannabifuran.

Dehydrocannabifuran
DCBF-C5

Chemical structure of cannabifuran.

Cannabifuran
CBF-C5

Isocannabinoids
Chemical structure of Δ7-trans-isotetrahydrocannabinol.

(−)-Δ7-trans-(1R,3R,6R)-
Isotetrahydrocannabinol

Chemical structure of Δ7-isotetrahydrocannabivarin.

(±)-Δ7-1,2-cis-
(1R,3R,6S/1S,3S,6R)-
Isotetrahydro-
cannabivarin

Chemical structure of Δ7-trans-isotetrahydrocannabivarin.

(−)-Δ7-trans-(1R,3R,6R)-
Isotetrahydrocannabivarin

Cannabicyclol-type (CBL)
Chemical structure of cannabicyclol.

(±)-(1aS,3aR,8bR,8cR)-
Cannabicyclol
CBL-C5

Chemical structure of cannabicyclolic acid A.

(±)-(1aS,3aR,8bR,8cR)-
Cannabicyclolic acid A
CBLA-C5 A

Chemical structure of cannabicyclovarin.

(±)-(1aS,3aR,8bR,8cR)-
Cannabicyclovarin
CBLV-C3

Cannabicitran-type (CBT)
Chemical structure of cannabicitran.

Cannabicitran
CBT-C5

Cannabichromanone-type (CBCN)
Chemical structure of cannabichromanone.

Cannabichromanone
CBCN-C5

Chemical structure of cannabichromanone-C3

Cannabichromanone-C3
CBCN-C3

Chemical structure of cannabicoumaronone.

Cannabicoumaronone
CBCON-C5

References

  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. ^ https://www.nwsci.com/customer/docs/SKUDocs/RMR/Technical%20Data_Extractions_03.28.18.pdf
  12. ^ "Table of Natural Cannabinoids" (PDF).