Cannabinoids () are compounds found in the cannabis plant or synthetic compounds that can interact with the endocannabinoid system. The most notable cannabinoid is the phytocannabinoid tetrahydrocannabinol (THC) (Delta-9-THC), the primary intoxicating compound in cannabis. Cannabidiol (CBD) is another major constituent of some cannabis plants. 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.

At least 113 distinct cannabinoids have been isolated from cannabis. 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-3-THC delta-4-THC delta-7-THC delta-8-THC delta-10-THC delta-11-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 See 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 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 to

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 to 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. The aromatic terpenoids begin to vaporize at , 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 CBCV CBD - CBDD ? CBDO CBDP CBDV CBE CBG 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 <220

Structural scheduling

+ Table of plant cannabinoids Cannabigerol-type (CBG) Cannabigerol(E)-CBG-C5 Cannabigerolmonomethyl 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 Amonomethyl ether(E)-CBGAM-C5 A Cannabigerovarinic acid A(E)-CBGVA-C3 A Cannabichromene-type (CBC) (±)-CannabichromeneCBC-C5 (±)-Cannabichromenic acid ACBCA-C5 A (±)-Cannabivarichromene, (±)-CannabichromevarinCBCV-C3 (±)-Cannabichromevarinicacid ACBCVA-C3 A Cannabidiol-type (CBD) (−)-CannabidiolCBD-C5 Cannabidiolmomomethyl etherCBDM-C5 Cannabidiol-C4CBD-C4 (−)-CannabidivarinCBDV-C3 CannabidiorcolCBD-C1 Cannabidiolic acidCBDA-C5 Cannabidivarinic acidCBDVA-C3 Cannabinodiol-type (CBND) CannabinodiolCBND-C5 CannabinodivarinCBND-C3 Tetrahydrocannabinol-type (THC) Δ9-TetrahydrocannabinolΔ9-THC-C5 Δ9-Tetrahydrocannabinol-C4Δ9-THC-C4 Δ9-TetrahydrocannabivarinΔ9-THCV-C3 Δ9-TetrahydrocannabiorcolΔ9-THCO-C1 Δ9-Tetrahydro-cannabinolic acid AΔ9-THCA-C5 A Δ9-Tetrahydro-cannabinolic acid BΔ9-THCA-C5 B Δ9-Tetrahydro-cannabinolic acid-C4A and/or BΔ9-THCA-C4 A and/or B Δ9-Tetrahydro-cannabivarinic acid AΔ9-THCVA-C3 A Δ9-Tetrahydro-cannabiorcolic acidA and/or BΔ9-THCOA-C1 A and/or B (−)-Δ8-trans-(6aR,10aR)-Δ8-TetrahydrocannabinolΔ8-THC-C5 (−)-Δ8-trans-(6aR,10aR)-Tetrahydrocannabinolicacid AΔ8-THCA-C5 A (−)-(6aS,10aR)-Δ9-Tetrahydrocannabinol(−)-cis-Δ9-THC-C5 Cannabinol-type (CBN) CannabinolCBN-C5 Cannabinol-C4CBN-C4 CannabivarinCBN-C3 Cannabinol-C2CBN-C2 CannabiorcolCBN-C1 Cannabinolic acid ACBNA-C5 A Cannabinol methyl etherCBNM-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)-tetrahydrocannabinol8,9-Di-OH-CBT-C5 Cannabidiolic acid Acannabitriol esterCBDA-C5 9-OH-CBT-C5 ester (−)-(6aR,9S,10S,10aR)-9,10-Dihydroxy-hexahydrocannabinol,CannabiripsolCannabiripsol-C5 (−)-6a,7,10a-Trihydroxy-Δ9-tetrahydrocannabinol(−)-Cannabitetrol 10-Oxo-Δ6a(10a)-tetrahydrocannabinolOTHC Cannabielsoin-type (CBE) (5aS,6S,9R,9aR)-CannabielsoinCBE-C5 (5aS,6S,9R,9aR)-C3-CannabielsoinCBE-C3 (5aS,6S,9R,9aR)-Cannabielsoic acid ACBEA-C5 A (5aS,6S,9R,9aR)-Cannabielsoic acid BCBEA-C5 B (5aS,6S,9R,9aR)-C3-Cannabielsoic acid BCBEA-C3 B Cannabiglendol-C3OH-iso-HHCV-C3 DehydrocannabifuranDCBF-C5 CannabifuranCBF-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)-CannabicyclolCBL-C5 (±)-(1aS,3aR,8bR,8cR)-Cannabicyclolic acid ACBLA-C5 A (±)-(1aS,3aR,8bR,8cR)-CannabicyclovarinCBLV-C3 Cannabicitran-type (CBT) CannabicitranCBT-C5 Cannabichromanone-type (CBCN) CannabichromanoneCBCN-C5 Cannabichromanone-C3CBCN-C3 CannabicoumarononeCBCON-C5

References