Cannabinoids (/kəˈnæbənɔɪdzˌˈkænəbənɔɪdz/) are compounds found in thecannabis plant or synthetic compounds that can interact with theendocannabinoid system.[1][2] The most notable cannabinoid is the phytocannabinoidtetrahydrocannabinol (THC) (Delta-9-THC), the primary intoxicating compound incannabis.[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.
| 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 |  |  |
| Cannabinoid | Quasi-psychedelic | Drug precursor | Legal status |
|---|---|---|---|
| CBCA,CBC | Legal in most countries | ||
| CBCVA,CBCV | |||
| CBDA,CBD | No | THC[6] | SeeCannabidiol § 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 | UNConvention on Psychotropic Substances | |
| THCB | |||
| THCCA,THCC | |||
| THCH | Yes | Legal in most countries | |
| THCPA,THCP | Yes | Legal in most countries | |
| THCVA,THCV |
| Cyclization reaction | Temperature |
|---|---|
| CBD →THC | 250 °C (482 °F) to 300 °C (572 °F)[6] |
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 |
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Upon heating, cannabinoid acidsdecarboxylate 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 ofdecarboxylation 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 tocannabis edibles, as THCA is not orally active. When consumed orally, theliver breaks down andmetabolizes THC into the more potent11-hydroxy-THC.
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Dry-herbvaporizers can be used to inhalecannabis in its flower form. There are 483 identifiable chemical constituents known to exist in thecannabis 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 bioactivetetrahydrocannabinol (THC), and other cannabinoids also found in cannabis (often legally sold as cannabinoid isolates) likecannabidiol (CBD),cannabichromene (CBC),cannabigerol (CBG),cannabinol (CBN), do not vaporize until near their respectiveboiling 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 avoidsynthetic 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-3-THC | ? |
| delta-4-THC | ? |
| delta-7-THC | ? |
| delta-8-THC | 175 °C (347 °F)-178 °C (352 °F)[11] |
| delta-10-THC | ? |
| delta-11-THC | ? |
| THC | 157 °C (315 °F)[11] |
| THCB | |
| THCC | |
| THCP | |
| THCV | <220[11] |
| Cannabigerol-type (CBG) | ||||
|---|---|---|---|---|
 Cannabigerol |  Cannabigerol |  Cannabinerolic acid A | Cannabigerovarin | |
 Cannabigerolic acid A |  Cannabigerolic acid A |  Cannabigerovarinic acid A | ||
| Cannabichromene-type (CBC) | ||||
 (±)-Cannabichromene |  (±)-Cannabichromenic acid A |  (±)-Cannabivarichromene, (±)-Cannabichromevarin |  (±)-Cannabichromevarinic | |
| Cannabidiol-type (CBD) | ||||
 (−)-Cannabidiol |  Cannabidiol |  Cannabidiol-C4 |  (−)-Cannabidivarin | Cannabidiorcol |
 Cannabidiolic acid |  Cannabidivarinic acid | |||
| Cannabinodiol-type (CBND) | ||||
 Cannabinodiol |  Cannabinodivarin | |||
| Tetrahydrocannabinol-type (THC) | ||||
Δ9-Tetrahydrocannabinol |  Δ9-Tetrahydrocannabinol-C4 |  Δ9-Tetrahydrocannabivarin |  Δ9-Tetrahydrocannabiorcol | |
 Δ9-Tetrahydro- |  Δ9-Tetrahydro- |  Δ9-Tetrahydro- |  Δ9-Tetrahydro- |  Δ9-Tetrahydro- |
 (−)-Δ8-trans-(6aR,10aR)- |  (−)-Δ8-trans-(6aR,10aR)- |  (−)-(6aS,10aR)-Δ9- | ||
| Cannabinol-type (CBN) | ||||
 Cannabinol |  Cannabinol-C4 |  Cannabivarin |  Cannabinol-C2 |  Cannabiorcol |
 Cannabinolic acid A |  Cannabinol methyl ether | |||
| Cannabitriol-type (CBT) | ||||
-trans-cannabitriol.png) (−)-(9R,10R)-trans- | -trans-cannabitriol.png) (+)-(9S,10S)-Cannabitriol |  (±)-(9R,10S/9S,10R)- |  (−)-(9R,10R)-trans- |  (±)-(9R,10R/9S,10S)- |
-tetrahydrocannabinol.png) 8,9-Dihydroxy-Δ6a(10a)- |  Cannabidiolic acid A |  (−)-(6aR,9S,10S,10aR)- |  (−)-6a,7,10a-Trihydroxy- | -tetrahydrocannabinol.png) 10-Oxo-Δ6a(10a)- |
| Cannabielsoin-type (CBE) | ||||
(5aS,6S,9R,9aR)- |  (5aS,6S,9R,9aR)- | |||
 (5aS,6S,9R,9aR)- |  (5aS,6S,9R,9aR)- |  (5aS,6S,9R,9aR)- | ||
 Cannabiglendol-C3 |  Dehydrocannabifuran |  Cannabifuran | ||
| Isocannabinoids | ||||
 (−)-Δ7-trans-(1R,3R,6R)- |  (±)-Δ7-1,2-cis- |  (−)-Δ7-trans-(1R,3R,6R)- | ||
| Cannabicyclol-type (CBL) | ||||
 (±)-(1aS,3aR,8bR,8cR)- |  (±)-(1aS,3aR,8bR,8cR)- |  (±)-(1aS,3aR,8bR,8cR)- | ||
| Cannabicitran-type (CBT) | ||||
 Cannabicitran | ||||
| Cannabichromanone-type (CBCN) | ||||
 Cannabichromanone |  Cannabichromanone-C3 |  Cannabicoumaronone | ||