THC

Generell information

THC är den mest framträdande cannabinoiden i Cannabis.

THC står bakom den huvudsakliga effekten av cannabisruset.

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  Trichomer som innehåller cannabinoiderna

Dekarboxylering av THCA till THC

När cannabis värms upp så omvandlas tetrahydrocannabinolsyra (THCA) till tetrahydrocannabinol (THC). Dekarboxylering är en funktion av värme och temperatur, högre temperatur gör att dekarboxyleringen tar kort tid, lägre temperatur ger längre tid. En längre uppvärmning på lägre temperatur är mest fördelaktig då man minskar risken för nedbrytning av THC till CBN.

Metodbeskrivning:

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Preferably, decarboxylation is carried out in a multi-step heating process in which the plant material is: i) heated to a first temperature for a first (relatively short) time period to evaporate off retained water and allow for uniform heating of the plant material; and ii) the temperature is increased to a second temperature for a second time period (typically longer than the first time period) until at least 95% conversion of the acid cannabinoids to their neutral form has occurred. Preferably the first step is conducted at a temperature in the range of 100° C. to 110° C. for 10–20 minutes. More preferably the first temperature is about 105° C. and the first time period is about 15 minutes. If the plant material is derived from cannabis plants having a high CBD content (defined as >90% CBD as a percentage of total cannabinoid content), the second temperature is preferably in the range from 115° C. to 125° C., preferably about 120° C. and the second time period is in the range from 45 to 75 minutes, preferably about 60 minutes. More preferably the second temperature is in the range from 135° C. to 145° C., preferably 140° C. and the second time period is in the range from 15 to 45 minutes, preferably about 30 minutes. In another embodiment, most preferred for a mass of plant material greater than 4 kg, the second temperature is in the range from 140° C. to 150° C., preferably 145° C. and the second time period is in the range from 55–90 minutes. The latter conditions are preferred for processing amounts of, for example, 4–6 kg of starting plant material and the exact figures, particularly time, may vary slightly with increased mass. If the plant material is derived from cannabis plants having a high THC content (defined as >90% THC as a percentage of total cannabinoid content), the second temperature is preferably in the range of 115° C. to 125° C., typically 120° C., and the second time period is preferably in the range of 45 minutes to 75 minutes, typically about 60 minutes. More preferably the second temperature is in the range of 100° C. to 110° C., typically 105° C., and the second time period is in the range of 60 to 120 minutes. In another embodiment, most preferred for a mass of plant material greater than 4 kg, the second temperature is in the range of 140° C. to 150° C., preferably 145° C., and the second time period is in the range of 45 to 55 minutes. — CannabisChris

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Biosyntes av THC

Biosyntesen av THC i Cannabis ser ut enligt följande diagram (som även visar CBD och CBN):

2019 rapporterades ett genombrott inom konstgjord biosyntes. Forskare vid Berkeley har lyckats genmodifiera jäst till att producera THC och CBD, men kan användas för att skapa diverse andra, och nya cannabinoider.

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To produce cannabinoids in yeast (Saccharomyces cerevisiae), UC Berkeley synthetic biologists first engineered yeast's native mevalonate pathway to provide a high flux of geranyl pyrophosphate (GPP) and introduced a hexanoyl-CoA biosynthetic pathway combining genes from five different bacteria. They then introduced Cannabis genes encoding the enzymes involved in olivetolic acid (OA) biosynthesis, a previously undiscovered prenyl transferase enzyme (CsPT4) and cannabinoid synthases. The synthases converted cannabigerolic acid (CBGA) to the cannabinoid acids THCA and CBDA, which, upon exposure to heat, decarboxylate to tetrahydrocannabinol (THC) and cannabidiol (CBD), respectively. ... "The economics look really good," Keasling said. "The cost is competitive or better than that for the plant-derived cannabinoids." — Science Daily (2019-02-27)

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Kemi

THC Utövar sin effekt genom att vara agonist till CB1-receptorer i hjärnan.

När THC binder till CB1-receptorer ändras aktiviteten hos intracellulära enzymer inkluderat cAMP (cykliskt adenosinmonofosfat) vars aktivitet reduceras. Mindre cAMP innebär mindre kinas A. Den reducerade aktiviteten påverkar kalium- och kalciumkanalerna och minskar frisläppandet av neurotransmittorer. Men processen leder paradoxalt nog ändå till ökad frisläppning av dopamin. Det beror på att dopaminergiska neuroner inte har CB1-receptorer. Dopaminfrisläppningen hämmas normalt av GABA och GABA-neuroner har i sin tur CB1-receptorer på axonterminalerna som THC binder till. Då hämmas frisläppandet av GABA vilket resulterar i ökad frisläppning av dopamin.

LD50-värdet för oral administrering hos hanråttor är är 1270 mg/kg, honråttor 730 mg/kg. Inhalerad LD50 är 42 mg/kg för båda könen.

THC har god löslighet i etanol. Ännu bättre i aceton, butan etc.

	Systematiskt namn	1-trans-delta^9-tetrahydrocannabinol
	Trivialnamn	tetrahydrocannabinol, THC, delta-9-THC
	Kemisk formel	C21H30O2
	Smältpunkt	200 C
	Kokpunkt	155-157 °C (vacuum, 0.07 mbar)
	Molmassa	314.46 g/mol
	Densitet	1.015 +- 0.06 g/cm3
	Löslighet	Läs under extrahering

Vattenlöslighet: 0.28 g/100 ml vid 23 C

Refraktivt index (uppskattat): 1.528 +- 0.02

Ytspänning (uppskattat): 35.0 +- 3.0 dyne/cm

Trådar på Magiska Molekyler om THC

Extraktion, isomerisering, acetylisering av THC