DELTA9-TETRAHYDROCANNABINOL Chemical Properties

Melting point:

<25 °C

alpha 

D20 -150.5° (c = 0.53 in CHCl3)

Boiling point:

bp0.02 200°

Density 

1.0536 (rough estimate)

refractive index 

1.5404 (estimate)

Flash point:

14 °C

storage temp. 

2-8°C

form 

ethanol solution

pka

pKa 10.6 (Uncertain)

Water Solubility 

2.8mg/L(23 ºC)

BCS Class

2/4

CAS DataBase Reference

1972-08-3

EPA Substance Registry System

Tetrahydrocannabinol (1972-08-3)

Safety Information

Hazard Codes 

F,T

Risk Statements 

11-39/23/24/25-23/24/25

Safety Statements 

16-7-45-36/37

RIDADR 

UN 1230 3/PG 2

WGK Germany 

1

HazardClass 

6.1(b)

PackingGroup 

III

Hazardous Substances Data

1972-08-3(Hazardous Substances Data)

Toxicity

LD50 (sesame oil emulsion) in male rats (mg/kg): 800 orally; 35.5. i.v.; 672 i.p. (Rosenkranz)

MSDS

• Language:English Provider:SigmaAldrich

DELTA9-TETRAHYDROCANNABINOL Usage And Synthesis

Description

Tetrahydrocannabinol (THC) is the main active compound in marijuana. It comes from the plant Cannabis sativa (cannabis), which is a dioecious (monoecious varieties do exist) annual herb naturally found in many tropic and temperate regions of the world. Many varieties of cannabis exist, and two related species (Cannabis indica and Cannabis ruderalia) are main sources of THC. Cannabis sativa is also known as hemp, although this name is not unique to the species; its stem is a source of fiber that has been used throughout history for hundreds of applications including rope, twine, paper, and cloth. Hemp seeds are edible and high in protein. The seeds are also a source of fatty oil that can be used for food, cosmetics, medicines, and as a fuel source. Cannabis contains chemicals called cannabinoids; of the 60 cannabinoids found in Cannabis, one is THC, , which is the psychoactive ingredient in marijuana. Marijuana is produced from the leaves and fl owers of cannabis, and hashish is a resin collected from the female fl owers. The THC content, which determines the effect of cannabis drugs, varies with plant structure, variety, and preparation. Buds and fl owers specifically cultivated for drug use have greater THC content than leaves. THC content may vary from a few tenths of a percent to more than 10%, but good quality marijuana has a THC content of approximately 10%, and good hashish and hashish oils generally have THC contents between 30% and 80%.

Chemical Properties

Thick Brown Oil

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.

Uses

Medical marijuana remains a controversial topic, but synthetic THC, dronabinol, marketedunder the trade name Marinol, has been available by prescription since 1986. Th edronabinol analog nabilone is another THC prescription drug marketed under the nameCesamet. Marinol and Cesamet, taken as capsules, have Food Drug Administration approvalas an antinausea agent and appetite stimulant (for AIDS patients), but they are also prescribedfor depression and muscle spasms. In 2005, Canada was the first country to approve Sativex,a cannabis spray that relieves pain in people with multiple sclerosis.

Uses

Δ9-Tetrahydrocannabinol (Δ9-THC) is a natural psychoactive compound found in plants of the genus Cannabis. This cannabinoid (CB) binds with high affinity to both the central CB1 receptor (Ki = 41 nM) and the peripheral CB2 receptor (Ki = 36 nM). Δ9-THC, working primarily through these receptors, has diverse effects on perception, cognition, pain sensitivity, body temperature, the immune system, fetal development, and more. This product is intended for forensic and research purposes.[Cayman Chemical]

Uses

It is the principal active constituent of cannabis. Agonist at CB1 and CB2 cannabinoid receptors. Antiemetic; appetite stimulant. Controlled substance (hallucinogen).

Definition

ChEBI: A diterpenoid that is 6a,7,8,10a-tetrahydro-6H-benzo[c]chromene substituted at position 1 by a hydroxy group, positions 6, 6 and 9 by methyl groups and at position 3 by a pentyl group. The principal psychoactive constituent f the cannabis plant, it is used for treatment of anorexia associated with AIDS as well as nausea and vomiting associated with cancer chemotherapy.

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 Distillation
A 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)).

brand name

Marinol (Unimed).

Therapeutic Function

Appetite stimulant

General Description

Brown amorphous semi-solid, viscous oil or chunky golden yellow solid.

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.

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