Cannabinoids in Cannabis

Cannabinoids in Cannabis

Cannabinoids in Cannabis

 

Cannabinoids are chemical compounds that interact with the cannabinoids receptors in the body and that have similar effects to those produced by Cannabis Sativa L. Prior to the discovery of the endocannabinod system, it was often speculated that cannabinoids interact with cell membranes but discovery of the first cannabinoid receptors in the 1980s resolved the ongoing debate.

 

Cannabinoid receptors

 

Cannabinoid receptors are present in all vertebrae, including mammals, birds, amphibians, fish and reptiles. At the time, there are two known types of cannabinoid receptors named CB1 and CB2 but there’s a lot of evidence suggesting that there may be more. Like opiates, cannabinoids affect the user by interacting with specific receptors, located within different parts of the central nervous system.

 

CB1 receptors are found mostly in the brain, specifically in the limbic system, including striatum and hippocampus and in the basal ganglia. They are also found in both male and female reproductive systems, anterior eye and retina.

 

CB2 receptors are predominantly found in the immune system or immune-derived cells. In vitro and animal models suggest that they appear to be responsible for immunomodulatory and other therapeutic effects. While found only in the peripheral nervous system, reports indicate that CB2 is expressed by a subpopulation of microglia in the human cerebellum.

 

Cannabinoids

 

There are three types of cannabinoids:

 

  • Phytocannabinoids – ones found in plants, mostly in the Cannabis genus – 146 of them are known so far but there are 50 more found in other plants
  • Endocannabinoids – ones our bodies make on their own
  • Synthetic cannabinoids – lab made cannabinoids

 

Phytocannabinoids

 

Although most phytocannabinoids are found in Cannabis plants, they occur in several other plant species besides Cannabis like Radula marginata, Echinacea angustifolia, Helichrysum umbraculigerum, Acmella oleracea, and Echinacea purpurea.

 

New cannabinoids are constantly being identified and the current known number of them is 146, although a very small number of them has been well researched. Some of the cannabinoids show similar structures so they’ve been grouped and classified in classes as – Cannabichromenes, Cannabicyclols, Cannabidiols, Cannabielsoins, Cannabigerols, Cannabinols and Cannabinodiols, Cannabitriols, Delta-8-tetrahydrocannabinols and Delta-9-tetrahydrocannabinols.

 

Some of the most abundant and well researched phytocannabinoids are:

 

THC, or delta-9-THC, is the most abundant and well-known cannabinoid present in cannabis and is responsible for cannabis’ most known psychoactive effects. THC is a mild painkiller or analgesic, stimulates appetite, reduces vomiting and nausea, suppresses muscle spasm and it also has antioxidant properties.

 

THCA is the main cannabinoid found in raw cannabis and a predecessor to THC. It has anti-inflammatory effects, reducing inflammation and also acts as an antiproliferative and antispasmodic, reducing seizures and convulsions and inhibiting cell growth in tumors/cancers.

 

CBDA, similar to THCA, is the main constituent in CBD rich or high CBD raw cannabis. It is a predecessor to CBD. CBDA selectively inhibits the COX-2 enzyme, contributing to cannabis’ anti-inflammatory effects, reducing inflammation and inhibiting tumor cell growth.

 

CBD is the second most researched and well-known cannabinoid. It acts as an antagonist at both the CB1 and CB2 receptors but it has a low binding affinity for both. This suggests that CBD’s mechanism of action is mediated by other receptors in the body and brain. CBD is known to reduce inflammation, offer pain relief, reduce vomiting and nausea, relieve anxiety, reduce seizures, suppress muscle spasms and promote bone growth.

 

CBN is a mildly psychoactive cannabinoid that is produced by degradation and oxidation of THC. There is usually very little to no CBN in a fresh raw cannabis plant but with time, especially if stored poorly, levels of CBN increase. It acts as a weak agonist at both the CB1 and CB2 receptors. CBN is known to reduce pain, suppress muscle spasms and convulsions and aid sleep.

 

CBG, or more correctly it’s acidic version CBGA, is the originator for both THC(A) and CBD(A). Without CBG there would be no THC or CBD, although CBG itself is found in very small amounts in cannabis plants. Another non-psychoactive cannabinoid, CBG is thought to kill or slow bacterial growth, inhibit cell growth in cancer and tumor cells, reduce inflammation and promote bone growth. It acts as a low-affinity antagonist at the CB1 receptor.

 

CBC is another non-psychoactive cannabinoid and is most frequently found in tropical cannabis strains. It is known to relieve pain, inhibit cell growth in tumor/cancer cells, reduce inflammation and promote bone growth.

 

THCV is another minor cannabinoid found in only certain strains of cannabis, most frequently in African landraces and their hybrids. It is very structurally similar to THC with an exception of presence of a propyl (3 carbon) group, instead of a pentyl (5 carbon) group, on the molecule. Though very similar in structure, their effects are quite different. THCV’s effects include a reduction in panic attacks, suppression of appetite and the promotion of bone growth. THCV acts as an antagonist at the CB1 receptor and a partial agonist at the CB2 receptor.

 

Endocannabinoids

 

First to be identified and isolated was Anandamide, very pharmacologically similar to THC but different in structure. It binds to the CB1 receptor and, to a lesser extent, CB2, where it acts as a partial agonist. Anandamide is found in almost all tissues in a wide range of animals but is also found in plants and in smaller amounts in chocolate. Anandamide has also been found in human and bovine maternal milk.

 

The rest of endocannabinoids include – 2-Arachidonoylglycerol (2-AG), 2-Arachidonyl glyceryl ether (noladin ether), N-Arachidonoyl dopamine (NADA), Virodhamine (OAE) and Lysophosphatidylinositol (LPI).

 

Synthetic cannabinoids

 

At first, synthetic cannabinoids were based on the structure of naturally occuring phytocannabinoids but have since become a category of their own, no longer being related to natural cannabinoids or based on the structure of endocannabinoids. A large number of synthetic cannabinoids have been produced and tested, first by a group of scientists gathered around Roger Adams in the 1940’s and later in a group led by Raphael Mechoulam, often dubbed the father of cannabis research.

 

Since only phytocannabinoids found in Cannabis are regulated (and banned) by law, synthetic cannabinoids have found their way on both legal and illegal markets. Products like K2, Galaxy or Spice provide for similar experiences like consuming cannabis but, unlike cannabis, they can cause serious damage even death. Some countries like the UK have serious problems with synthetic cannabinoids, causing addiction and crime related to that addiction but almost all countries in which synthetic cannabinoids are sold have reported serious health issues and in most cases death. This has resulted in some countries banning synthetic cannabinoids but they can easily be found on the internet and illegal or “black” markets.

 

Here is the full list of cannabinoids found in Cannabis

 

*Cannabinoid Name**Acronym*
1CannabigerovarinCBGV
2Cannabigerovarinic acidCBGVA
3CannabigerolCBG
4Cannabigerolic acidCBGA
5Ο-Methlycannabigerol
6Cannabigerolic acid methylether
7Cannabinerolic acid
8Cannabinerol
9Carmagerol
10rac-6′-Epoxycannabigerol
11rac-6′-Epoxycannabigerolic acid
12rac-6′-Epoxycannabinerol
13rac-6′-Epoxycannabinerolic acid
14γ-Eudesmyl cannabigerolate
15γ-Cadinyl cannabigerolate
16Sesquicannabigerol
17Deprenyl Ο-methyl cannabigerolic acid (Amorfrutin 2)
185-Acetyl-4-hydroxycannabigerol
19Acetylcannabigeroquinol
20Cannabigeroquinone
21Abnormal cannabigerol
22Acetyl abnormal hydrocannabigeroquinol
23Abnormal cannabigeroquinol
242′-Hydroxy-1′, 2′-dihydrocannabichromene (Cyclo-CBG)
25Cannabiorcichromene
26Cannabiorcichromenic acid
27Chlorcannabiorcichromenic acid
28CannabivarichromeneCBCV
29Cannabichromevarinic acid
30CannabichromeneCBC
31Cannabichromenic acid
324-Acetoxycannabichromene
33Anthopogochromenic acid
34Confluentin
35Daurichromenic acid
368′-Hydroxyisocannabichromene
374-Acetoxycannabichromene
38Cannabidiorcol
39CannabidivarinCBDV
40Cannabidivarinic acid
41nor-Cannabidiol
42CannabidiolCBD
43Ο-Methlycannabidiol
44Ο-Propylcannabidiol
45Ο-Pentylcannabidiol
46Cannabidiolic acidCBDA
47CBDA-THC ester
48Ferruginene C
49Cannabioxepane
50Cannabinodivarin
51Cannabinodiol
52Cannabifuran
53Dehydrocannabifuran
54trans-Δ-8-TetrahydrocannabinolΔ-8-THC
55trans-Δ-8-Tetrahydrocannabinolic acid
5610α-Hydroxy trans-Δ-8-tetrahydrocannabinol
5710β-Hydroxy trans-Δ-8-tetrahydrocannabinol
5811-Acetoxy-Δ-8-tetrahydrocannabinoic acid
5910-Hydroxy-9-oxo-Δ-8-tetrahydrocannabinol
60Δ-9-trans-Tetrahydrocannabiorcol
61Δ-9-trans-Tetrahydrocannabiorcolic acid
62Δ-9-trans-TetrahydrocannabivarinTHCV
63Δ-9-trans-Tetrahydrocannabivarinic acid
64Δ-9-trans-nor-Tetrahydrocannabinol
65Δ-9-trans-nor-Tetrahydrocannabinolic acid
66Δ-9-trans-TetrahydrocannabinolΔ-9-THC
67Δ-9-trans-Tetrahydrocannabinolic acid A
68Δ-9-trans-Tetrahydrocannabinolic acid B
698α-Hydroxy-Δ-9-trans-tetrahydrocannabinol
708β-Hydroxy-Δ-9-trans-tetrahydrocannabinol
718-Oxo-Δ-9-trans-tetrahydrocannabinol
72Ο-Propyl-Δ-9-trans-tetrahydrocannabinol
73Ο-Pentyl-Δ-9-trans-tetrahydrocannabinol
742-Formyl-Δ-9-trans-tetrahydrocannabinol
75β-Fenchyl Δ-9-trans-Tetrahydrocannabinolate
76α-Fenchyl Δ-9-trans-Tetrahydrocannabinolate
77Bornyl Δ-9-trans-Tetrahydrocannabinolate
78epi-Bornyl Δ-9-trans-Tetrahydrocannabinolate
79α-Terpinyl Δ-9-trans-Tetrahydrocannabinolate
804-Terpinyl Δ-9-trans-Tetrahydrocannabinolate
81γ-Eudesmyl Δ-9-trans-Tetrahydrocannabinolate
82α-Cadinyl Δ-9-trans-Tetrahydrocannabinolate
83Hexahydrocannabinol
84Hydroxy Δ-9,11-hexahydrocannabinol
85Methylen-bis Δ-9-trans-Tetrahydrocannabinol (Cannabisol)
86Tetrahydrocannabinol epoxide
87Δ-9-trans-Tetrahydrocannabinol glycol (cannabiripsol)
886a,7,10a-Trihydroxy-Δ-9-tetrahydrocannabinol
89Δ-9-cis-Tetrahydrocannabivarin
90Δ-9-cis-Tetrahydrocannabinol
91Cannabicitran (citrilidene-cannabis)CBT
92Cannabiorcicitran
93Bis-nor cannabitriol
94Bis-nor-Cannabitriol isomer
9510-Ο-Ethyl bis-nor cannabitriol
96Isocannabitriol
97Cannabitriol
98Cannabitriol isomer
9910-Ο-Ethyl cannabitriol isomer
10010-Oxo-Δ6a(10a)-tetrahydrocannabinol
1019,10-Anhydrocannabitirol
102Cannabiglendol
1037,8-Dehydro-10-Ο-ethylcannabitriol
104Δ-7-cis-Isotetrahydrocannabivarin
105Δ-7-trans-Isotetrahydrocannabivarin
106Δ-7-trans-isotetrahydrocannabinol
107Bis-nor-cannabielsoin
108Bis-nor-Cannabielsoic acid B
109CannabielsoinCBE
110Cannabielsoic acid A
111Cannabielsoic acid B
112Ferruginene A
113Ferruginene B
114Cannabiorcicyclol
115Cannabiorcicyclolic acid
116Cannabicyclovarin
117CannabicyclolCBL
118Cannabicyclolic acid
119Anthopogocyclolic acid
120Rhododaurichromanic acid A
121Cannabiorcol
122nor-Cannabivarin
123CannabivarinCBV
124nor-Cannabinol
125CannabinolCBN
126Cannabinolic acid
127Ο-Methylcannabinol
128Ο-Propylcannabinol
129Ο-Penthylcannabinol
1307-Hydroxcannabinol
1318-Hydroxycannabinol
1328-Hydroxcannabinolic acid
1337,8-Dihydrocannabinol
1344-Terpenyl cannabinolate
135Cannabicoumaronone
136Cannabicourmarononic acid
137Bisnor-Cannabichromanone
138Cannabichromanone
139(6a*R*)-Cannabichromanone B
140(6a*R*)-Cannabichromanone C
141Cannabichromanone
142Cannabimovone
143Anhydrocannabimovone
144Demethyldecarboxyamorfrutin A
145TetrahydrocannabiphorolTHCP
146CannabidiphorolCBDP

 

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