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Cannabis (drug)

marijuanacannabispot
Tetrahydrocannabinol (THC) is one of at least 113 cannabinoids identified in cannabis.
The main psychoactive part of cannabis is tetrahydrocannabinol (THC), one of the 483 known compounds in the plant, including at least 65 other cannabinoids.

Dimethylheptylpyran

DMHPDimethylheptyltetrahydrocannabinol
THC, along with its double bond isomers and their stereoisomers, is one of only three cannabinoids scheduled by the UN Convention on Psychotropic Substances (the other two are dimethylheptylpyran and parahexyl).
Dimethylheptylpyran (DMHP, 3-(1,2-dimethylheptyl)-Δ 6a(10a) -THC, 1,2-dimethylheptyl-Δ 3 THC, A-40824, or EA-2233) is a synthetic analog of THC, which was invented in 1949 during attempts to elucidate the structure of Δ 9 -THC, one of the active components of Cannabis.

Dronabinol

MarinolSyndrossynthetic pill form
However, dronabinol is a synthetic form of THC approved by the FDA as an appetite stimulant for people with AIDS and antiemetic for people receiving chemotherapy.
The International Nonproprietary Name Dronabinol, also known as Marinol and Syndros, is a trade name for a specific form of tetrahydrocannabinol, sold as an appetite stimulant, antiemetic, and sleep apnea reliever.

Parahexyl

synhexyl
THC, along with its double bond isomers and their stereoisomers, is one of only three cannabinoids scheduled by the UN Convention on Psychotropic Substances (the other two are dimethylheptylpyran and parahexyl).
Parahexyl (Synhexyl, n-hexyl-Δ 3 THC) is a synthetic homologue of THC, which was invented in 1949 during attempts to elucidate the structure of Δ 9 -THC, one of the active components of cannabis.

Cannabis

marijuanahemppot
THC is an active ingredient in Nabiximols, a specific extract of Cannabis that was approved as a botanical drug in the United Kingdom in 2010 as a mouth spray for people with multiple sclerosis to alleviate neuropathic pain, spasticity, overactive bladder, and other symptoms. In the Cannabis plant, THC occurs mainly as tetrahydrocannabinolic acid (THCA, 2-COOH-THC, THC-COOH).
To satisfy the UN Narcotics Convention, some cannabis strains have been bred to produce minimal levels of tetrahydrocannabinol (THC), the principal psychoactive constituent.

Cannabinoid receptor type 1

CB 1 CB 1 receptorCB1
The actions of THC result from its partial agonist activity at the cannabinoid receptor CB 1 (K i = 10 nM ), located mainly in the central nervous system, and the CB 2 receptor (K i = 24 nM ), mainly expressed in cells of the immune system.
It is activated by: endocannabinoids, a group of retrograde neurotransmitters that include anandamide and 2-arachidonoylglycerol (2-AG); plant phytocannabinoids, such as the compound THC which is an active ingredient of the psychoactive drug cannabis; and, synthetic analogs of THC.

Cannabinoid receptor type 2

CB 2 CB 2 receptorCB2
The actions of THC result from its partial agonist activity at the cannabinoid receptor CB 1 (K i = 10 nM ), located mainly in the central nervous system, and the CB 2 receptor (K i = 24 nM ), mainly expressed in cells of the immune system.
It is closely related to the cannabinoid receptor type 1, which is largely responsible for the efficacy of endocannabinoid-mediated presynaptic-inhibition, the psychoactive properties of tetrahydrocannabinol, the active agent in cannabis, and other phytocannabinoids (plant cannabinoids).

Single Convention on Narcotic Drugs

Single Convention on Narcotic Drugs 1961Schedule ISingle Convention on Narcotic Drugs of 1961
Cannabis as a plant is scheduled by the Single Convention on Narcotic Drugs (Schedule I and IV).
. . The parallel existence of the Single Convention and the 1971 Convention have led to certain illogical effects such as the fact that a plant (cannabis) containing at most 3% of a principal element is dealt with more severely than the pure substance at 100% (tetrahydrocannabinol or THC).

Secondary metabolite

secondary compoundssecondary compoundnatural products
Like most pharmacologically-active secondary metabolites of plants, THC is a lipid found in cannabis, assumed to be involved in the plant's self-defense, putatively against insect predation, ultraviolet light, and environmental stress.

Nabiximols

Sativexmedicinal formulations
THC is an active ingredient in Nabiximols, a specific extract of Cannabis that was approved as a botanical drug in the United Kingdom in 2010 as a mouth spray for people with multiple sclerosis to alleviate neuropathic pain, spasticity, overactive bladder, and other symptoms.
Its principal active cannabinoid components are the cannabinoids: tetrahydrocannabinol (THC) and cannabidiol (CBD).

Psychoactive drug

psychoactivepsychotropicdrug
THC is the principal psychoactive constituent of cannabis.

Anandamide

ArachidonoylethanolamideArachidonoylethanolamineAEA
The presence of these specialized cannabinoid receptors in the brain led researchers to the discovery of endocannabinoids, such as anandamide and 2-arachidonoyl glyceride (2-AG).
Cannabinoid receptors were originally discovered as being sensitive to Δ 9 -tetrahydrocannabinol (Δ 9 -THC, commonly called THC), which is the primary psychoactive cannabinoid found in cannabis.

11-Nor-9-carboxy-THC

THC-COOHCarboxy THCCarboxy-THC
This metabolite is still psychoactive and is further oxidized to 11-nor-9-carboxy-THC (THC-COOH).
11-Nor-9-carboxy-Δ 9 -tetrahydrocannabinol (11-COOH-THC or THC-COOH), often referred to as 11-nor-9-carboxy-THC or THC-11-oic acid, is the main secondary metabolite of tetrahydrocannabinol (THC), which is formed in the body after cannabis is consumed.

Controlled Substances Act

Schedule ISchedule IISchedule III
It is specifically still listed under Schedule I by US federal law under the Controlled Substances Act for having "no accepted medical use" and "lack of accepted safety".

Tetrahydrocannabinolic acid

THCA
In the Cannabis plant, THC occurs mainly as tetrahydrocannabinolic acid (THCA, 2-COOH-THC, THC-COOH).
Tetrahydrocannabinolic acid (THCA, 2-COOH-THC; conjugate base tetrahydrocannabinolate) is a precursor of tetrahydrocannabinol (THC), the active component of cannabis.

11-Hydroxy-THC

11-OH-THC11-hydroxy-Δ 9 -THC
THC is metabolized mainly to 11-OH-THC by the body.
11-Hydroxy-Δ 9 -tetrahydrocannabinol (11-OH-THC), usually referred to as 11-hydroxy-THC, is the main active metabolite of tetrahydrocannabinol (THC), which is formed in the body after decarboxylated cannabis is consumed.

Olivetol

olivetolic acid
Geranyl pyrophosphate and olivetolic acid react, catalysed by an enzyme to produce cannabigerolic acid, which is cyclized by the enzyme THC acid synthase to give THCA.
Olivetol, also known as 5-pentylresorcinol or 5-pentyl-1,3-benzenediol, is an organic compound found in certain species of lichen; it is also a precursor in various syntheses of tetrahydrocannabinol.

Tetrahydrocannabinolic acid synthase

THCATHC acid synthaseTHCA synthase
Geranyl pyrophosphate and olivetolic acid react, catalysed by an enzyme to produce cannabigerolic acid, which is cyclized by the enzyme THC acid synthase to give THCA.
THCA is the direct precursor of tetrahydrocannabinol (THC), the principal psychoactive component of cannabis, which is produced from various strains of Cannabis sativa.

Cannabigerol

CBGCBG oilCBGA
Geranyl pyrophosphate and olivetolic acid react, catalysed by an enzyme to produce cannabigerolic acid, which is cyclized by the enzyme THC acid synthase to give THCA.
During growth, most of the cannabigerol is converted into other cannabinoids, primarily tetrahydrocannabinol (THC) or cannabidiol (CBD), leaving about 1% cannabigerol in the plant.

Cannabinoid receptor

cannabinoid receptorscannabinoidCB 1
The actions of THC result from its partial agonist activity at the cannabinoid receptor CB 1 (K i = 10 nM ), located mainly in the central nervous system, and the CB 2 receptor (K i = 24 nM ), mainly expressed in cells of the immune system.
THC, as well as the two major endogenous compounds identified so far that bind to the cannabinoid receptors —anandamide and 2-arachidonylglycerol (2-AG)— produce most of their effects by binding to both the CB 1 and CB 2 cannabinoid receptors.

Raphael Mechoulam

Mechoulam
THC was first isolated in 1964 by Raphael Mechoulam and Yechiel Gaoni at the Weizmann Institute of Science in Israel.
Mechoulam is best known for his work (together with Y. Gaoni) in the isolation, structure elucidation and total synthesis of Δ 9 -tetrahydrocannabinol, the main active principle of cannabis and for the isolation and the identification of the endogenous cannabinoids anandamide from the brain and 2-arachidonoyl glycerol (2-AG) from peripheral organs together with his students, postdocs and collaborators.

Cannabidiol

CBDCBD oilEpidiolex
Female cannabis plants contain at least 113 cannabinoids, including cannabidiol (CBD), thought to be the major anticonvulsant that helps people with multiple sclerosis; and cannabichromene (CBC), an anti-inflammatory which may contribute to the pain-killing effect of cannabis.
It may be supplied as CBD oil containing only CBD as the active ingredient (no included tetrahydrocannabinol [THC] or terpenes), a full-plant CBD-dominant hemp extract oil, capsules, dried cannabis, or as a prescription liquid solution.

Cannabichromene

CBC
Female cannabis plants contain at least 113 cannabinoids, including cannabidiol (CBD), thought to be the major anticonvulsant that helps people with multiple sclerosis; and cannabichromene (CBC), an anti-inflammatory which may contribute to the pain-killing effect of cannabis.
It bears structural similarity to the other natural cannabinoids, including tetrahydrocannabinol (THC), tetrahydrocannabivarin (THCV), cannabidiol (CBD), and cannabinol (CBN), among others.

Cannabinoid

cannabinoidsendocannabinoidendocannabinoids
Tetrahydrocannabinol (THC) is one of at least 113 cannabinoids identified in cannabis. The presence of these specialized cannabinoid receptors in the brain led researchers to the discovery of endocannabinoids, such as anandamide and 2-arachidonoyl glyceride (2-AG).
The most notable cannabinoid is the phytocannabinoid tetrahydrocannabinol (THC), the primary psychoactive compound in cannabis.

CYP2C9

2C9cytochrome P450 2C9CYP 2C9
Metabolism occurs mainly in the liver by cytochrome P450 enzymes CYP2C9, CYP2C19, and CYP3A4.