1972-08-3 Usage
Description
DELTA9-TETRAHYDROCANNABINOL, commonly known as THC, is the main active compound in marijuana. It is a diterpenoid derived from the Cannabis sativa plant, which is naturally found in many tropical and temperate regions of the world. This psychoactive constituent is responsible for the various effects of marijuana on perception, cognition, pain sensitivity, body temperature, the immune system, and more. It is available in the form of a thick brown oil and is marketed under the brand name Marinol (Unimed).
Uses
1. Medical Applications:
DELTA9-TETRAHYDROCANNABINOL is used as an antinausea agent and appetite stimulant for patients with AIDS and cancer. It is particularly effective in treating anorexia associated with AIDS and nausea and vomiting associated with cancer chemotherapy.
2. Pharmaceutical Industry:
Used in the Pharmaceutical Industry:
DELTA9-TETRAHYDROCANNABINOL is used as a controlled substance (hallucinogen) for the development of prescription drugs such as Marinol and Cesamet. These drugs are approved by the Food and Drug Administration for their antinausea and appetite-stimulating properties.
3. Forensic and Research Purposes:
DELTA9-TETRAHYDROCANNABINOL is used as a natural psychoactive compound for forensic and research purposes. It binds with high affinity to both the central CB1 receptor and the peripheral CB2 receptor, allowing for the study of its diverse effects on various physiological processes.
4. Pain Management:
In 2005, Canada was the first country to approve Sativex, a cannabis spray that relieves pain in people with multiple sclerosis. DELTA9-TETRAHYDROCANNABINOL is a key component of this spray, providing relief for patients suffering from chronic pain.
5. Cannabis Industry:
DELTA9-TETRAHYDROCANNABINOL is the principal active constituent of cannabis, making it a crucial component in the production of marijuana and hashish. It is responsible for the psychoactive effects of these substances, which are used for recreational and medicinal purposes. The THC content in these products can vary, with good quality marijuana having a THC content of approximately 10%, and good hashish and hashish oils generally having THC contents between 30% and 80%.
6. Hemp Industry:
Although not directly a use for DELTA9-TETRAHYDROCANNABINOL, the Cannabis sativa plant from which it is derived is also known as hemp. Hemp is a versatile resource, with its stem being used for the production of fiber for rope, twine, paper, and cloth. Additionally, hemp seeds are edible and high in protein, and their fatty oil can be used for food, cosmetics, medicines, and as a fuel source.
Originator
Unimed (USA)
History
THC was first isolated from hashish in 1964 by Raphael Mechoulam (1930–) and Yehiel
Gaoni at the Weizmann Institute. In the
early 1990s, the specific brain receptors affected by THC were identified. These receptors
are activated by a cannabinoid neurotransmitter called arachidonylethanolamide, known as
anandamide. Anandamide was named by Mechoulam using ananda, which is the Sanskrit
word for ecstasy. Anandamide is thought to be associated with memory, pain, depression, and
appetite. THC is able to attach to and activate anandamide receptors. These receptors are actually
called THC receptors rather than anandamide receptors because researchers discovered
that THC attaches to these receptors before anandamide was discovered. The areas of the brain
with the most THC receptors are the cerebellum, the cerebral cortex, and the limbic system.
This is why marijuana affects thinking, memory, sensory perception, and coordination.
Manufacturing Process
δ-9-Tetrahydrocannabinol (THC, also known as dronabinol) is the main
biologically active component in the Cannabis plant extracted from the resin of
Cannabis sativa (marihuana, hashish).One kg of the fine powdered marijuana plant material [average % of THC was
about 5.21%] was macerated with 6 L hexanes (Hexanes GR from EM
Sciences) in a percolator (9" in diameter from the top and 20" long, cone
shaped) for 24 hours at room temperature and filtered. The macerate was
reextracted with 5 L hexanes for another 24 hours. The hexane extracts were
combined and evaporated under reduced pressure at low temperature to give
110.7 g residue (11.07% extractives). The % of THC in the hexane extract
was 41.21%.Column Chromatography.The hexane extract (110.7 g) was mixed with 150 g silica gel (silica gel 60,
Art.# 9385-3) and 50 ml hexane. The air dried slurry was transferred to the
top of a silica gel column (800 g silica gel 60, particle size 0.04-0.063 mm,
from EM Science, Art.# 9385-3). The column was eluted with hexane:ether
mixtures in a manner of increasing polarities. Fractions were collected and TLC
screened (analytical silica gel plates, developing system: Hexane:Ether
(80:20), Visualizing agent: Fast blue). The fractions collected with hexane (3
L) and hexane-ether (95:5, 2 L) were discarded. The following fractions
collected with hexane-ether (95:5, 3 L) and hexane-ether (9:1, 5 L) were
combined and evaporated to yield 77.2 g of residue. GC analysis of the
residue showed THC concentration to be 54.74%.Fractional DistillationA portion (30.5 g) of the residue collected above was subjected to fractional
distillation under reduced pressure (0.1-0.15 mm/Hg). The temperature was
slowly raised to 125°C and the materials collected were kept separate. The
temperature was then raised between 140°-160°C where the major fraction
was collected (14 g). GC analysis showed >96% THC. Further purification on
a silica gel column gives THC with at least 98% purity. An improvement of this
process includes the use of high pressure liquid chromatography (HPLC). The
preparation of dronabinol and related compounds have employed acidcatalyzed electrophilic condensation of a 5-alkylresorcinol such as 5-npentylresorcinol (commonly known as olivetol) and a menthadienol, followed
by cyclization; yield of desired product is about 17-22% (Petrzilka et al., Helv.
Chim. Acta, 52, 1102 (1969)).
Therapeutic Function
Appetite stimulant
Air & Water Reactions
Slightly soluble in water.
Reactivity Profile
DELTA9-TETRAHYDROCANNABINOLis very unstable to light and high temperatures. DELTA9-TETRAHYDROCANNABINOL should be protected from air during all handling due to its extreme instability. . Flammable and/or toxic gases are generated by the combination of alcohols with alkali metals, nitrides, and strong reducing agents. They react with oxoacids and carboxylic acids to form esters plus water. Oxidizing agents convert them to aldehydes or ketones. Alcohols exhibit both weak acid and weak base behavior. They may initiate the polymerization of isocyanates and epoxides.
Fire Hazard
Flash point data for DELTA9-TETRAHYDROCANNABINOL are not available; however, DELTA9-TETRAHYDROCANNABINOL is probably combustible.
Biological Activity
Cannabinoid receptor agonist (K i values are 5.05 and 3.13 nM for CB 1 and CB 2 receptors respectively; EC 50 values are 6, 0.4 and 8 nM at CB 1 , CB 2 and GPR55 receptors respectively). Major psychoactive constituent of marijuana.
Clinical Use
Dronabinol (synthetic △9-THC) i s a n antinauseant approved for the treatment of nausea and vomiting associated with cancer chemotherapy in patients who have failed to respond adequately to conventional antiemetics. A related cannabinoid, nabilone, was introduced in Canada for his indication in 1982.
Safety Profile
Poison by intraperitoneal and intravenous routes. Moderately toxic by ingestion. Experimental reproductive effects. Questionable carcinogen with experimental tumorigenic and teratogenic data. Human mutation data reported. A hallucinatory drug. When heated to decomposition it emits acrid smoke and irritating fumes. See also CANNABIS.
Check Digit Verification of cas no
The CAS Registry Mumber 1972-08-3 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,9,7 and 2 respectively; the second part has 2 digits, 0 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 1972-08:
(6*1)+(5*9)+(4*7)+(3*2)+(2*0)+(1*8)=93
93 % 10 = 3
So 1972-08-3 is a valid CAS Registry Number.
InChI:InChI=1/C21H30O2/c1-5-6-7-8-15-12-18(22)20-16-11-14(2)9-10-17(16)21(3,4)23-19(20)13-15/h11-13,16-17,22H,5-10H2,1-4H3/t16-,17-/m0/s1
1972-08-3Relevant articles and documents
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Adams et al.
, (1941)
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Synthesis of Para (-)-Δ8-THC Triflate as a Building Block for the Preparation of THC Derivatives Bearing Different Side Chains
Hoffmann, Grete,Daniliuc, Constantin G.,Studer, Armido
, p. 563 - 566 (2019)
A two-step synthesis of para (-)-Δ8-THC-OTf that can be used as building block for late-stage introduction of side chains to the tetrahydrodibenzopyran core of THC by cross-coupling chemistry is presented. No protecting groups are needed, and (
Cannabidiol as the Substrate in Acid-Catalyzed Intramolecular Cyclization
Marzullo, Paola,Foschi, Francesca,Coppini, Davide Andrea,Fanchini, Fabiola,Magnani, Lucia,Rusconi, Selina,Luzzani, Marcello,Passarella, Daniele
, p. 2894 - 2901 (2020)
The chemical reactivity of cannabidiol is based on its ability to undergo intramolecular cyclization driven by the addition of a phenolic group to one of its two double bonds. The main products of this cyclization are Δ9-THC (trans-Δ-9-tetrahydrocannabinol) and Δ8-THC (trans-Δ-8-tetrahydrocannabinol). These two cannabinoids are isomers, and the first one is a frequently investigated psychoactive compound and pharmaceutical agent. The isomers Δ8-iso-THC (trans-Δ-8-iso-tetrahydrocannabinol) and Δ4(8)-iso-THC (trans-Δ-4,8-iso-tetrahydrocannabinol) have been identified as additional products of intramolecular cyclization. The use of Lewis and protic acids in different solvents has been studied to investigate the possible modulation of the reactivity of CBD (cannabidiol). The complete NMR spectroscopic characterizations of the four isomers are reported. High-performance liquid chromatography analysis and 1H NMR spectra of the reaction mixture were used to assess the percentage ratio of the compounds formed.
METHODS FOR CONVERTING CBD TO TETRAHYDROCANNABINOLS
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Paragraph 0081, (2021/07/24)
This disclosure provides a method for converting CBD to a tetrahydrocannabinol featuring the use of cheap and non-toxic aluminum isopropoxide as a catalyst. The method comprises (a) providing a reaction mixture comprising a catalyst in an organic solvent, wherein the catalyst comprises aluminum isopropoxide; (b) adding a reagent comprising CBD to the reaction mixture; (c) mixing the reaction mixture and allowing a reaction for converting CBD to a tetrahydrocannabinol to occur for a predetermine period of time; (d) removing the catalyst by filtration upon the completion of the reaction; (e) removing the organic solvent; and (f) eluting the tetrahydrocannabinol from the organic phase.
CATALYTIC CONVERSATION OF CANNABIDIOL AND METHODS THEREOF
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Paragraph 0022, (2021/11/20)
A method of converting cannabidiol (CBD) into Δ9-Tetrahydrocannabinol (Δ9-THC) and Δ8-Tetrahydrocannabinol (Δ8-THC). The method provides a polar aprotic solvent such as Tert-Butyl Methyl Ether, Tetrahydrofuran, dicloromethane, or chloroform. Cannabidiol starting material mixes into the polar aprotic solvent in a chemical reactor to make a cannabinoid solution. Adding a metallic catalyst capable of performing intramolecular hydroalkoxylation to the cannabinoid solution and mixing it converts the cannabidiol starting material into Δ9-Tetrahydrocannabinol (Δ9-THC) and Δ8-Tetrahydrocannabinol (Δ8-THC) in a ratio of at least 6:1. The catalyst is a metal such as a transition metal or is selected from the group consisting of ruthenium, aluminum, iron, gold, silver, copper, platinum, and combinations thereof. In one embodiment a co-catalyst is used such as a triflate salt. Regulating the temperature of the reaction to less than 20° C. yields a predominance of Δ9-THC, i.e. Δ9-THC is more than 75% of the cannabinoid mix.
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