Acetone extract health

Tetrahydrocannabinol

Δ 9 -tetrahydrocannabinol [ ˌtetraˌhydroˌkanabiˈnoːl ] (THC) belongs to the cannabinoids and is the main active ingredient of cannabis (hashish, marijuana). It was first isolated in 1964 by Raphael Mechoulam at the Weizmann Institute of Science in Israel.

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Table of Contents

Incidence and definition

Tetrahydrocannabinol occurs exclusively in hemp (Cannabis sativa) pre. The unfertilized female inflorescences are particularly rich in THC (about 6 to 20 %), in the rest of the plant the proportion is much lower (just under 1 %), in the seeds of the plant there is no THC at all. The leaves near the flower contain ca. 5-6 %. Female and male plants differ greatly in active ingredient content.

Biosynthesis

Tetrahydrocannabinol is present in the cannabis plant predominantly as THC acid. Cannabigerolic acid is formed by enzymatic condensation from the two precursors geranyl pyrophosphate and olivetolic acid, which is then enzymatically converted to tetrahydrocannabinolic acid. Heat and UV radiation cause the acid to decarboxylate to THC.

Extraction

THC is very lipophilic. It can be isolated by extraction from THC-containing plant material using nonpolar and weakly polar solvents such as n-Alkanes, acetone, isopropyl alcohol, or ethanol are suitable. After the solvent evaporates, a resinous, oil-like extract remains. The composition of the extract depends on the choice of the solvent. Under suitable conditions, very high THC concentrations can be achieved. This extract is also called "oil", "hash oil", "honeyoil" or "red oil".

With n-Butane (lighter gas) allows lipophilic ingredients to be extracted from the plant material at very low temperatures; however, this method involves a high risk of fire and explosion. Butane evaporates already at room temperature. The extract obtained has an appearance similar to amber, at room temperature it is thick and draws threads like synthetic resin. When cooled, it solidifies relatively quickly.

In addition to THC, the extract contains other cannabinoids; when more polar extractants such as ethanol are used, correspondingly more polar substances may be present, such as chlorophyll, alkaloids (trigonelline, hordenine), amino acids, amino sugars [2] , evt. also undissolved fine parts of the source material. The extract can be further purified through appropriate processes.

Forms of consumption

Consumption can take place in different ways. The most common form of consumption is smoking hashish or marijuana pure or mixed with tobacco. At the end of 19. At the beginning of the twentieth century, "knaster" (today we would say "weed") was often smoked in Europe in rural areas in special knaster pipes or as hand-rolled cigarettes – but these contained lower levels of THC than today's joints. THC-containing material is also often smoked with the help of special smoking accessories such as bongs and pipes or vaporized with a vaporizer and then inhaled. In addition, THC is also found in food. beverages processed. Since THC is lipophilic, it is often used in high-fat foods such as milk, cakes, muffins, etc. Processed. THC-containing foods often have a stronger effect than the comparable smoked dose, but are also much more difficult to dose and only take effect with up to four hours delay. This must be taken into account especially when driving.

The pure substance THC cannot be administered intravenously without an emulsifier due to its poor dissolution behavior caused by strong lipophilicity.

Pharmacology

The mechanism of action of cannabinoids is poorly understood in its entirety.

In the action of THC, the endocannabinoid receptors CB1 and CB2 are crucial: central (affecting the brain) and peripheral (affecting the body) effects are mediated by the CB1 receptor, the CB2 receptor occurs in the periphery and in immune cells of the brain. This importance of these receptors is initially not related to THC, they have an important function in the body.

Anandamides are endogenous substances that, like acetylcholine, act as neurotransmitters in synapses and bind to these same cannabinoid receptors. In this way, excitation is transmitted in the synapse.

But THC also binds to these receptors, thus causing an unnaturally increased stimulus transmission in these synapses. This is what causes the CNS symptoms such as the feeling of happiness. relaxation as well as the analgesic (pain-relieving) effect.

In the brain stem, where vital functions such as breathing are coordinated, very few to none of these receptors are present, which may indicate that these processes are not directly affected by THC. In the hippocampus, where short-term memory is located, there are many of these receptors. This is where it is decided whether information is important and how it is processed further, d.h. whether it is forgotten or stored in long-term memory. This explains why THC has a significant effect on short-term memory.

Immune cells have CB receptors, so cannabinoids have an effect on the immune system.

Endocannabinoid receptors are further found in the spleen.

The body-related effects are definitely also mediated centrally. Thus, the degree of wakefulness (sleep resp. Narcosis vs. Effect on respiratory-. Heart rate. For example, THC generally has a heart rate-slowing effect on anesthetized animals, while awake animals react with a pulse increase (as do humans).

Metabolism

THC is first oxidized in humans predominantly to 11-OH-THC (11-hydroxy-THC). This breakdown product is also psychoactive and is further metabolized to 11-nor-9-carboxy-THC (THC-COOH, THC-carboxylic acid). Over 100 different THC metabolites have been identified in humans and animals, but the former two are the main products. Metabolism occurs mainly in the liver and by the cytochrome P450 enzymes 2C9, 2C19 and 3A4. More than 65% of THC is excreted in the stool and approx. 20% in the urine. The main metabolite in urine is THC-COOH esterified with glucuronic acid and free THC-COOH, while feces is dominated by 11-OH-THC [3] .

Toxicity: Lethal dose

LD50 in mice is 42 mg/kg body weight intravenously and 482 mg/kg by oral administration; in rhesus monkeys, death by respiratory arrest and cardiac failure occurs after intravenous administration of 128 mg/kg body weight. LD50 value is not determined in humans. Cannot be reliably extrapolated. Aming a rough (and low) estimate of the potential peroral LD50 for humans at 150 mg/kg body weight, a 70 kg person would have a 50% chance of dying after acute oral consumption of 10.5 g THC. This amount is contained in about 130-260 g of a cannabis product with 4-8 % THC content. It should be noted, however, that THC is absorbed much more poorly through the intestines than through the lungs. [5]

Side effect

AcuteSide effects and effects of THC often overlap. Mild nausea, dry mouth, dizziness, listlessness, and ravenous appetite occur frequently. Furthermore, there may be a loss of temporal, more rarely, and at high doses, spatial and personal orientation. Depersonalization is observed in isolated cases. Very rarely hallucinations occur, controversial is the occurrence of so-called flashbacks. Very rarely, even small amounts can cause anxiety, agitation, and immobility; this is especially true for unintentional and undetected use, such as when THC-containing foods are unknowingly consumed.

Chronic: The following side effects may occur with chronic THC use:

– THC can cause latent (pre-existing, hidden) psychosis even with moderate use. – Prolonged chronic use can have a negative effect on drive and memory. – When THC-containing plant parts are smoked, the usual side effects (nicotine excluded) of smoking are added: atherosclerosis, as well as a marked increased risk of heart and brain infarcts, oral, laryngeal, lung, and bladder cancers. These side effects are but the form of consumption. Not attributable to the native active ingredient THC. When mixed with tobacco, which is very common, all the dangers of nicotine addiction are compounded.

There is no evidence that THC is teratogenic (damaging to fertility), nevertheless pregnant and breastfeeding women should refrain from consuming THC, as damage to the unborn or breastfed child cannot be safely ruled out.

Medical use

Semisynthetic THC, called dronabinol, is available in Germany and other countries as a prescription narcotic (trade name Marinol ® ) applicable in anorexia and cachexia in HIV and AIDS patients, and as an antiemetic in nausea and vomiting under cytostatic or antipsychotic treatment. Radiation therapy in the context of cancer therapy.

The fully synthetic THC derivative nabilone has a similar indication.

THC is also in the clinical trial phase for the treatment of glaucoma and autoimmune diseases such as multiple sclerosis, Crohn's disease and ulcerative colitis.

That THC effectively reduces tics in Tourette's syndrome sufferers was confirmed by the results of a six-week study at Hannover Medical School.

Analogues in other stimulants

The anandamide contained in chocolate docks at the same receptor as THC. It has a much weaker effect than THC, but is still active.

THC in road traffic

THC affects the central nervous system, so people should refrain from using machines and driving vehicles after consumption. The police can detect traces of THC during driver controls by means of a sweat, saliva or urine test or by examining the blood even a long time after consumption. Detection time depends mainly on the pattern of use (duration, type of ingestion, frequency, dose) and can range from one week to two months in urine. At present, however, the legal situation has not yet been clearly decided, but there is a threat of fines of at least 250 euros, driving bans of up to three months and four points in Flensburg. The police officers on site can only carry out orienting pre-tests, the blood sample is later examined in a laboratory and the amount of THC and its degradation products is determined. From a legal point of view, a misdemeanor has been committed if THC is still detectable in the blood. In the decision of the Bavarian VGH from 25. January 2006, Az. 11 CS 05.1711, stands: The current medical-scientific state of knowledge does not justify, already from a THC concentration of 1.0 ng/ml in the blood of a motor vehicle driver, an increase in the risk for traffic safety as so certain in the sense of § 11 para. 7 FeV states that the driver's license must be revoked without further clarification of the facts. In the case of occasional use of cannabis and driving with a THC concentration between 1.0 and 2.0 ng/ml, before a possible revocation of the driving license according to § 14 Abs. 1 S. 4 FeV to obtain a medical-psychological expert opinion.FeV § 11 Abs. 7, FeV § 14 Abs. 1 S. 4, StVG § 3 Abs. 1 However, this only applies if no driving errors have been made. In many cases, the administrative authority (driving license) orders a review of fitness to drive (MPU) to prove the fitness to drive.

However, trials with chronically ill MS patients have suggested that treatment with THC or THC-like substances by no means impairs driving ability. Tests with several test subjects, some of whom only received a placebo, have clearly confirmed this.

In Switzerland, since the beginning of 2005, it has also been possible to detect THC with a drug test (engl. "Drug Wipe") at traffic controls, despite the rumor that the rapid tests used by the police give false results in more than 80 % of the cases [6] [7].

Other unofficial authorities speak of an abuse of the traffic law, because even patients with opiates and other strong drugs remain entitled to drive, while the THC user is not only punished if he is under direct influence of the drug, but also if the consumption has already taken place days ago. This applies to all urine tests, as they do not directly detect THC, but a degradation product of THC, the tetrahydrocannabinolic acid (THC-COOH, also called THC-carboxylic acid). The cannabinolic acid no longer has an intoxicating effect. However, it is excreted from the body relatively slowly and at different rates depending on the constitution, and can thus be detected in the urine for a long time, sometimes even for weeks. In contrast, saliva and sweat tests such as the drug tests cited above directly detect THC with sufficient sensitivity.

THC content of common black market products

Conventional outdoor marijuana grown in Central Europe contains an average of about 6% THC, while marijuana grown under artificial light and specially bred for high THC content (also known incorrectly as "gene hemp") has an active ingredient content of about 20%. In the USA, such cultivations started in the 1970s; especially in the Netherlands, they continued since the 1980s, so that the average THC-content of the so-called "Nederwiet" was last (2004) at about 20. Nevertheless, reports of allegedly increased THC levels of up to 50 times are to be considered as exaggerated beyond measure. U.S. researchers pointed out that the extremely low levels given as a comparison for cannabis seized in the 1960s/70s (z. T. below 1%) may be due to the fact that at that time the whole plants including stems and leaves were analyzed, whereas today only the actually consumed inflorescences are examined.

Hashish contains on average between 5 and 10% THC, although – as with marijuana – the range can be very wide: High-quality hashish can also contain over 20% THC. Hashish produced in the Netherlands from high-quality marijuana (which, however, has only a very small market share) sometimes contains up to 40% THC. A 2006 Leiden University study examined eleven herbal cannabis samples from Dutch coffee shops, and THC levels ranged from 11.7% to 19.1%. Two comparative samples of herbal cannabis from Dutch pharmacies contained 12.2% or. 16.5% THC. [8]

Hashish oil, which is rarely available on the black market, can contain up to 90% THC, depending on the production method used. If "cheap" solvents of moderate purity are used that contain toxic by-products or denaturants, or if solvents are insufficiently removed, consumption can lead to health problems.

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