Delta-8-Tetrahydrocannabinol (Delta-8-THC, Δ8-THC) is a psychoactive cannabinoid found in the cannabis plant. It is an isomer of Delta-9-Tetrahydrocannabinol (Delta-9-THC, Δ9-THC), the compound commonly known as THC. Delta-8-THC has antiemetic, anxiolytic, orexigenic, analgesic, and neuroprotective properties.
3D model (JSmol)
CompTox Dashboard (EPA)
|Molar mass||314.5 g/mol|
|Boiling point||383.5±42.0 °C|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Delta-8-THC is slightly less potent than Delta-9-THC, but its psychological and physiological effects are qualitatively similar, essentially meaning it will still intoxicate, but to a lesser degree. Delta-8-THC may cause increased heart rate, reddening of the eyes, dizziness, dryness of the mouth and throat, paresthesia, tinnitus, increased body awareness, weakness, muscle tension or tremor, reduced motor coordination, fatigue, sleepiness, changes in visual perception, altered visual imagery, enhancement of colors or contrasts, time distortion, changes in auditory perception, euphoria, tranquility, relaxation, racing thoughts, dreamy introspective states, or difficulty in thinking, speaking, reading, or remembering.
The pharmacodynamic profile of Delta-8-THC is similar to that of Delta-9-THC. It is an agonist of CB1 and CB2 Cannabinoid receptors with about half the potency of Delta-9-THC in most but not all measures of biological activity. Delta-8-THC has been reported to have a Ki value of 44 ± 12 nM at the CB1 receptor and 44 ± 17 nM at the CB2 receptor. These values are higher than those typically reported for Delta-9-THC at the same receptors, indicating that Delta-8-THC binds to cannabinoid receptors less efficiently than Delta-9-THC.
The pharmacokinetic profile of Delta-8-THC is also similar to that of Delta-9-THC. Following ingestion in humans, hepatic cytochrome P450 enzymes including CYP2C9 and CYP3A4 first convert Delta-8-THC into 11-hydroxy-Δ8-tetrahydrocannabinol (11-OH-Δ8-THC). Next, dehydrogenase enzymes convert 11-OH-Δ8-THC into 11-nor-Δ8-tetrahydrocannabinol-9-carboxylic acid (11-nor-Δ8-THC-9-COOH, also known as Δ8-THC-11-oic acid). Finally, Δ8-THC-11-oic acid undergoes glucuronidation by glucuronidase enzymes to form 11-nor-Δ8-tetrahydrocannabinol-9-carboxylic acid glucuronide (Δ8-THC-COOH-glu). This final product is then excreted in the urine.
Physical and chemical propertiesEdit
Delta-8-THC is a tricyclic terpenoid. Although it has the same chemical formula as Delta-9-THC, one of its carbon-carbon Double bonds is located in a different position. This difference in structure increases the chemical stability of Delta-8-THC relative to Delta-9-THC, lengthening shelf life and allowing the compound to resist undergoing oxidation to cannabinol over time. Like other cannabinoids, Delta-8-THC is very lipophilic (log P = 7.4). It is an extremely viscous, colorless oil at room temperature.
Delta-8-THC has a double bond (a) between the carbon atoms labeled 8 and 9. Delta-9-THC has a double bond (a) between the carbon atoms labeled 9 and 10.
The partial synthesis of Delta-8-THC was published in 1941 by Roger Adams and colleagues at the University of Illinois. In 1942, the same research group studied its physiological and psychoactive effects after oral dosing in human volunteers. Total syntheses of Delta-8-THC were achieved by 1965. In 1966, the chemical structure of Delta-8-THC isolated from cannabis was characterized using modern methods by Richard L. Hively, William A. Mosher, and Friedrich W. Hoffmann at the University of Delaware. A stereospecific synthesis of Delta-8-THC from olivetol and verbenol was reported by Raphael Mechoulam and colleagues at the Weizmann Institute of Science in 1967. Delta-8-THC was often referred to as Delta-6-THC (Δ6-THC) in early scientific literature, but this name is no longer conventional among most authors.
Society and cultureEdit
Since the 2018 United States farm bill was signed into law in December 2018, Delta-8-THC products isomerized from compliant sources (including industrial hemp and derivative cannabidiol extracts) have been sold by a range of digital vendors and a more limited array of brick and mortar retailers, including head shops. Ranging from bulk quantities of unrefined distillate to prepared edibles and atomizer cartridges suffused with cannabis-derived terpenes, they are usually marketed as federally legal alternatives to their Delta-9-THC counterparts. However, the legal status of Delta-8-THC at the federal level is in question with some believing that the Oct. 2020 DEA IFR addressing "synthetics" applied to Delta-8 and other hemp derivatives allowed by the Farm Bill.
Beginning in late 2020, Delta-8-THC began to attract the attention of many cannabis consumers throughout the United States. Thought of as an alternative to traditional cannabis use, especially in areas where marijuana is illegal, the news of Delta 8-THC spread quickly via news agencies, cannabis publications, blogs, and podcasts which attracted a storm of social media attention.
As of early 2021, Delta-8 is one of the fastest growing segments of products derived from hemp.
Delta-8-THC has been studied as a potential treatment for glaucoma, corneal injury, and chemotherapy-induced nausea and vomiting (CINV). A clinical trial in Israel involving 108 cancer patients with CINV was registered with the NIH in 2005, but the study was never completed. In-vitro studies have investigated the effects of Delta-8-THC on cultured neuroblastoma cells and oral cancer cells. Some photooxygenation products of Delta-8-THC have been found to possess biological activity in-vitro. Although Delta-8-THC is a minor constituent of medical cannabis, no large clinical studies have been published on Delta-8-THC alone for any medical condition as of 2021 according to the NIH database.
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