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Δ-8-Tetrahydrocannabinol

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Δ-8-Tetrahydrocannabinol
Names
IUPAC name
6,6,9-trimethyl-3-pentyl-6a,7,10,10a-tetrahydrobenzo[c]chromen-1-ol
Other names
  • Δ8-THC
  • Δ-8-THC
  • Δ8-THC
  • δ-8-THC
  • (−)-trans-Δ8-tetrahydrocannabinol
  • (−)-trans-Δ8-tetrahydrocannabinol
  • Δ6-THC
  • Δ-6-THC
  • Δ6-THC
  • Δ1(6)-THC
  • (−)-trans-Δ6-tetrahydrocannabinol
  • (−)-trans-Δ6-tetrahydrocannabinol
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.165.076Edit this at Wikidata
KEGG
UNII
  • InChI=1S/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/h9,12-13,16-17,22H,5-8,10-11H2,1-4H3
    Key: HCAWPGARWVBULJ-UHFFFAOYSA-N
  • CCCCCC1=CC(=C2C3CC(=CCC3C(OC2=C1)(C)C)C)O
Properties
C21H30O2
Molar mass 314.5 g/mol
Density 1.0±0.1 g/cm3
Boiling point 383.5±42.0 °C
Except where otherwise noted, data are given for materials in theirstandard state(at 25 °C [77 °F], 100 kPa).

Δ-8-tetrahydrocannabinol(delta-8-THC,[a]Δ8-THC) is apsychoactivecannabinoidfound in theCannabisplant.[1][2][3]It is anisomerofdelta-9-tetrahydrocannabinol(delta-9-THC, Δ9-THC), the compound commonly known as THC, with which it co-occurs inhemp;natural quantities of ∆8-THC found in hemp are low.[4]

Psychoactive effects are similar to that of Δ9-THC, withcentraleffects occurring by binding tocannabinoid receptorsfound in various regions of the brain. During the production process of convertingcannabidiolextracted fromhempto ∆8-THC, toxic chemical reagents are used, which can contaminate the product. In the US, ∆8-THC products are neither mandatorily tested norFDAapproved, hence concern has been raised about their safety. In addition, as of 2022, the safety profile of regular, long-term delta-8-THC consumption is unknown.

Partial synthesisof ∆8-THC was published in 1941 byRoger Adamsand colleagues at theUniversity of Illinois. After the2018 United States farm billwas signed, ∆8-THC productspartially synthesizedfrom compliant sources (includingindustrial hempand derivativecannabidiolextracts) experienced a rise in popularity; THC products have been sold in licensed, regulated recreational cannabis andmedical cannabis industries within the United Statesonly inCalifornia,Pennsylvania,and regulated in Michigan and Oregon. According to a March 2024 study,[5]11% of UStwelfth gradershave used ∆8-THC over the past 12 months.

Effects[edit]

∆8-THC is moderately lesspotentthan Δ9-THC.[6][7]This means that while its effects are similar to that of Δ9-THC, it would take more ∆8-THC to achieve a comparable level of effect.[8]

A 1973 study testing the effects of ∆8-THC in dogs and monkeys reported that a single oral dose of 9,000 milligrams per kilogram of body mass (mg/kg) was nonlethal in all dogs and monkeys studied.[9][10]The same study reported that themedian lethal doseof ∆8-THC in rats was comparable to that of ∆9-THC.[9]Both isomers of THC have been found to cause a transient increase in blood pressure in rats,[11]although the effects of cannabinoids on thecardiovascular systemare complex.[12]Animal studies indicate that ∆8-THC exerts many of itscentraleffects by binding tocannabinoid receptorsfound in various regions of the brain, including thecerebral cortex,thalamus,basal ganglia,hippocampus,andcerebellum.[13][14]

Production[edit]

∆8-THC is typically synthesized fromcannabidiolextracted fromhemp,[15]as the natural quantities of ∆8-THC found in hemp are low. This is calledsemisynthesisor partial synthesis. The reaction often yields a mixture that contains other cannabinoids and unknown reaction by-products. As a result, most products sold as ∆8-THC are not actually pure ∆8-THC.[15]Little is known about the identity and the health effects of the impurities.[15]Some manufacturers of ∆8-THC may usehousehold chemicalsin the synthesis process, potentially introducing harmfulcontaminants.[16]In that sense, ∆8-THC can be called a "semisynthetic phytocannabinoid" or semisynthetic endocannabinoid, as it is obtained by (partial) chemical synthesis. It is not to be confused with the termsynthetic cannabinoid,however.

Safety[edit]

As of 2022, the safety profile, including risks ofpsychosisandaddictionafter regular, long-term delta-8-THC use was unknown.[17]

As of 2022, there have been at least 104adverse event reportsmade regarding ∆8-THC,[16]and at least two deaths associated with ∆8-THC products.[18][19]US nationalpoison control centersreceived 2,362 exposure cases of delta-8 THC products between January 1, 2021, and February 28, 2022; 58% of these exposures involved adults, and 70% thought they required medical care.[16]

Pharmacology[edit]

Mechanism of action[edit]

Thepharmacodynamicprofile of ∆8-THC is similar to that of ∆9-THC.[6][7]It is apartial agonistofCB1andCB2cannabinoid receptorswith about half the potency of ∆9-THC in most but not all measures of biological activity.[20][21][22]∆8-THC has been reported to have aKivalueof 44 ± 12 nM at the CB1receptor and 44 ± 17 nM at the CB2receptor.[23]These values are higher than those typically reported for ∆9-THC (CB1Ki= 40.7 nM) at the same receptors, indicating that ∆8-THC binds to cannabinoid receptors less efficiently than ∆9-THC.[24]

Pharmacokinetics[edit]

Thepharmacokineticprofile of ∆8-THC is also similar to that of ∆9-THC.[6][7]Following ingestion in humans,hepaticcytochrome P450enzymes includingCYP2C9andCYP3A4first convert ∆8-THC into 11-hydroxy-Δ8-tetrahydrocannabinol (11-OH-Δ8-THC).[25][26]Next,dehydrogenaseenzymes 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).[26][27]Finally, Δ8-THC-11-oic acid undergoesglucuronidationbyglucuronidaseenzymes to form 11-nor-Δ8-tetrahydrocannabinol-9-carboxylic acid glucuronide (Δ8-THC-COOH-glu),[26][27]which is then excreted in the urine.[28][29]

Physical and chemical properties[edit]

∆8-THC is a tricyclicterpenoid.Although it has the same chemical formula as ∆9-THC, one of its carbon-carbondouble bondsis located in a different position.[6]In ∆8-THC, the double bond is between the eighth and ninth carbons in structure, while in Δ9-THC, the double bond is between the ninth and tenth carbons in structure.

∆8-THC has a double bond (a) between the carbon atoms labeled 8 and 9.
∆9-THC has a double bond (a) between the carbon atoms labeled 9 and 10.

This difference in structure increases the chemical stability of ∆8-THC relative to ∆9-THC, lengthening shelf life and allowing the compound to resist undergoingoxidationtocannabinolover time.[20]Like other cannabinoids, ∆8-THC is verylipophilic(logP= 7.4[30]). It is an extremely viscous, colorless oil at room temperature.[31]

While ∆8-THC is naturally found in plants of theCannabisgenus,[3]this compound can also be produced in an industrial or laboratory setting by exposingCBDto acids and heat.[32][33][34]Solvents that may be used during this process includemethylene chloride,toluene,andhexane.[34]VariousBrønstedorLewis acidsthat may be used to facilitate thisisomerizationincludetosylic acid,indium(III) triflate,trimethylsilyl trifluoromethanesulfonate,hydrochloric acid,andsulfuric acid.[34][35]Because it is possible for chemical contaminants to be generated during the process of converting CBD to ∆8-THC, such asΔ10-THC,9-OH-HHCand other side products, as well as the potentially toxic chemical reagents used during manufacture, concern has been raised about the safety of untested or impure ∆8-THC products.[35][36]

The ongoing controversy regarding the legal status of ∆8-THC in the U.S. (seebelow) is complicated bychemical nomenclature.According to a 2019 literature review published inClinical Toxicology,the termsynthetic cannabinoidtypically refers to afull agonistofCB1andCB2cannabinoid receptors.[37]According to the review, the following is stated:

"The psychoactive (and probably the toxic) effects of synthetic cannabinoid receptor agonists are likely due to their action as full receptor agonists and their greater potency at CB1 receptors."

However, ∆8-THC and ∆9-THC arepartial agonistsof cannabinoid receptors.[21]They are less potent and less toxic than many synthetic cannabinoids.[38]It has not been definitively proven if full agonism is the reason for toxicity since ∆9-THC has been shown to act as a full CB1agonist on specific CB1receptors located in the hippocampus section of the brain.[39]Furthermore, the synthetic cannabinoidEG-018acts as a partial agonist.[40]The classical cannabinoid structure is that of a dibenzopyran structure. This group includes THC. THC interacts with a different spot inside of the CB1receptor than synthetic cannabinoid such JWH-018. This may explain the latter's toxicity.[41]

History[edit]

Thepartial synthesisof ∆8-THC was published in 1941 byRoger Adamsand colleagues at theUniversity of Illinois.[42]In 1942, the same research group studied its physiological and psychoactive effects after oral dosing in human volunteers.[43]Total synthesesof ∆8-THC were achieved by 1965.[44]In 1966, the chemical structure of ∆8-THC isolated from cannabis was characterized using modern methods by Richard L. Hively, William A. Mosher, and Friedrich W. Hoffmann at theUniversity of Delaware.[45]Astereospecificsynthesis of ∆8-THC fromolivetolandverbenolwas reported byRaphael Mechoulamand colleagues at theWeizmann Institute of Sciencein 1967.[46]∆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.[47]

Regulation[edit]

United States[edit]

Federal laws[edit]

In 1937, ∆9-THC was effectively made illegal with the passage of the (since-repealed)Marihuana Tax Act,which made growing cannabis require a tax stamp. President Ronald Reagan re-enacted mandatory sentences[48][49]for cannabis-related offenses.[50]As of 1 September 2023, 24 states havelegalizedcannabis, with others having reduced penalties.

The2018 United States farm bill,signed into law in December 2018, states the following:

"The termhempmeans the plant Cannabis sativa L. and any part of that plant, including the seeds thereof and all derivatives, extracts, cannabinoids, isomers, acids, salts, and salts of isomers, whether growing or not,with a delta-9 tetrahydrocannabinol concentration of not more than 0.3 percent on a dry weight basis."

Despite claims of legality by manufacturers, independent testing of products from retail has often revealed significant levels of ∆9-THC. Many of these levels are well above one legal threshold.[51][52][53]

In October 2020, theDEAInterim Final Rule[54]addressedsynthetic cannabinoids.Some believed that this also applied to ∆8-THC products and other hemp derivatives allowed by the Farm Bill.[55][56]

FDA[edit]

∆8-THC has not been evaluated or approved by theFDA.Consequently, Δ-8-tetrahydrocannabinol is not recognized under theFederal Food, Drug, and Cosmetic Actas safe and effective for any use.[57]The FDA has taken action against businesses that have illegally marketed ∆8-THC for therapeutic use.[58]The FDA has also taken action against businesses that sold ∆8-THC in forms that closely resemble (typically non-psychoactive) food products such as chips or cookies.[59]

Individual states[edit]

While most states have not arrested significant numbers of people for ∆8-THC, a handful have been arrested and charged, leading to confusion as to its legal status in those states.[60][61][62][63]

In 2021, one store owner inMenomonee Falls, Wisconsinwas facing a sentence of up to 50 years for allegedly selling ∆8-THC products with illegal amounts of ∆9-THC.[64][65]Other raids and arrests have happened due to the ∆9-THC content of these products inNorth Carolina,andTexas,among other places.[66][67][68]In 2022,Catoosa County, GeorgiaSheriff Sisk announced to prosecute stores distributing ∆8-THC with non-compliant ∆9-THC levels: "The products the sheriffs office has purchased and tested all contain significant levels of ∆9.[We have the] evidence needed to move forward with prosecution and seizures. "[69]There are also issues related to incidental manufacture of ∆9THC, as ∆9is produced as an intermediate product in the process of acid catalyzed ring closure of cannabidiol.[70]

There are multiple court decisions pertaining to the legality of Delta-8 THC.AK Futures LLC vs Boyd Street Distro, LLC(2022) was one of the earliest decisions made in a federal court, stating "On the available record, the delta-8 THC in AK Futures’ e-cigarette liquid appears to fit comfortably within the statutory definition of “hemp.” ".[71]United States vs. Rice,however, came to the opposite conclusion, "In short, Delta-8 remains a controlled substance. Although Delta-10 was not directly referenced in the DEA’s letter, there is no basis (in the record before the court) to believe that the DEA will treat Delta-10 in a different manner.".United States vs. Plancartealso states, "There is no legal D9-THC threshold for synthetic derivatives of THC. A gray area is whether Delta-8 THC is legal; it probably is when it occurs naturally in hemp, but this is not clear."[72]

∆8-THC products have been sold in licensed, regulated recreational cannabis andmedical cannabis industries within the United StatesincludingCalifornia[73]andPennsylvania's licensed, regulated medical cannabis system since 2020.[74][75][76][77] BothMichigan[78]and the state ofOregonhave regulated Delta-8-THC products sold under their regulated cannabis system.[79]

Products and prevalence of use[edit]

Common Delta-8 products range from bulk quantities of unrefineddistillateto preparedcannabis ediblesandatomizer cartridges.[80][81]In the US, they are usually marketed as federally legal alternatives to their ∆9-THC counterparts.[82]

∆8-THC productspartially synthesizedfrom compliant sources (includingindustrial hempand derivativecannabidiolextracts) experienced a rise in popularity in the US following the passage of the 2018 Farm Bill.[83]This led to it being sold by a diverse range of retailers, includinghead shops,smoke shops,vape shops,dispensaries,gas stations,andconvenience stores.[84][85]

In March 2024, a study of self-reportedprevalenceof Δ8-THC use among UStwelfth graderswas published: Of those reporting Δ8-THC use, 35% had used it at least 10 times in the past 12 months. Consumption was lower in Western than Southern and in states, where Δ8-THC was regulated versus not regulated.[86]

Research[edit]

Although it is a minor constituent ofmedical cannabis,no large clinical studies have been conducted on delta-8-THC alone as of 2022.[87]One study (ongoing as of November 2023) is focused on determining the degree of pharmacologic and pharmacokinetic similarity between ∆8-THC and ∆9-THC.[88]

See also[edit]

References[edit]

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Notes[edit]

  1. ^Commonly spoken as "delta-8 THC", or just "delta 8".

External links[edit]

Retrieved from "https://en.wikipedia.org/w/index.php?title=Δ-8-Tetrahydrocannabinol&oldid=1229725278"