Cannabinoid

Uses

Medical uses include the treatment of nausea due to chemotherapy, spasticity, and possibly neuropathic pain. Common side effects include dizziness, sedation, confusion, dissociation and "feeling high".

Cannabinoid receptors

Before the 1980s, it was often speculated that cannabinoids produced their physiological and behavioral effects via nonspecific interaction with cell membranes, instead of interacting with specific membrane-bound receptors. The discovery of the first cannabinoid receptors in the 1980s helped to resolve this debate. These receptors are common in animals, and have been found in mammals, birds, fish, and reptiles. At present, there are two known types of cannabinoid receptors, termed CB1 and CB2, with mounting evidence of more. The human brain has more cannabinoid receptors than any other G protein-coupled receptor (GPCR) type.

Cannabinoid receptor type 1

CB1 receptors are found primarily in the brain, more specifically in the basal ganglia and in the limbic system, including the hippocampus and the striatum. They are also found in the cerebellum and in both male and female reproductive systems. CB1 receptors are absent in the medulla oblongata, the part of the brain stem responsible for respiratory and cardiovascular functions. CB1 is also found in the human anterior eye and retina.

Cannabinoid receptor type 2

CB2 receptors are predominantly found in the immune system, or immune-derived cells with varying expression patterns. While found only in the peripheral nervous system, a report does indicate that CB2 is expressed by a subpopulation of microglia in the human cerebellum. CB2 receptors appear to be responsible for immunomodulatory and possibly other therapeutic effects of cannabinoid as seen in vitro and in animal models.

Synthetic cannabinoids

Historically, laboratory synthesis of cannabinoids was often based on the structure of herbal cannabinoids, and a large number of analogs have been produced and tested, especially in a group led by Roger Adams as early as 1941 and later in a group led by Raphael Mechoulam. Newer compounds are no longer related to natural cannabinoids or are based on the structure of the endogenous cannabinoids.

Synthetic cannabinoids are particularly useful in experiments to determine the relationship between the structure and activity of cannabinoid compounds, by making systematic, incremental modifications of cannabinoid molecules.

When synthetic cannabinoids are used recreationally, they present significant health dangers to users. In the period of 2012 through 2014, over 10,000 contacts to poison control centers in the United States were related to use of synthetic cannabinoids.

Medications containing natural or synthetic cannabinoids or cannabinoid analogs:

Other notable synthetic cannabinoids include:

Table of plant cannabinoids

Table of plant cannabinoids
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
(−)-cis9-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

See also

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