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Tetrahydrocannabinol

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Tetrahydrocannabinol
Tetrahydrocannabinolmolecule.png 2DTetrahydrocannabinol.png
General
Systematic name Tetrahydrocannabinol
Other names Dronabinol

THC
delta9-tetrahydrocannabinol
Marinol
Deltanyne

Molecular formula C21H30O2
SMILES CCCCCC1=CC2=C([C@@H]3C=C
(CC[C@H]3C(O2)(C)C)C)C(=C1)O
Molar mass Molar mass::314.469 g/mol
Appearance Light yellow resinous oil
CAS number CAS number::1972-08-3
Properties
Solubility in water 2800 mg/L (23°C)
Melting point Melting point::80°C
Boiling point Boiling point::157°C
Chiral rotation [α]D -150.5 deg at 20 deg C/D °
Structure
Hazards
MSDS Material safety data sheet
Main hazards psychoactive
NFPA 704

NFPA 704 svg.png

1
3
0
Flash point 212.7°C
RTECS number HP8225000
Related compounds
Related Phenol delta8-tetrahydrocannabinol
Except where noted otherwise, data are given for
materials in their standard state (at 25 °C, 100 kPa)
Disclaimer and references

Tetrahydrocannabinol (THC) is a complex non-polar molecule that is the primary psychoactive ingredient in marijuana. In its pure form, THC has several medical applications and can be used to treat eating disorders as well as regurgitation responses for chemotherapy patients. THC heavily stimulates cannabinoid receptors in the brain due to its similar structure with anandamide, a natural regulatory chemical for pleasure, visual acuity, balance, and memory.

Properties

3D model of THC.

Tetrahydrocannabinol (THC) was first isolated in Rehovot, Israel in 1964 by Raphael Mechoulam, Yechiel Gaoni, and Habib Edery from the Weizmann Institute.[1] THC is a non-polar complex molecule composed of 21 carbon atoms, 30 hydrogen atoms, and 2 oxygen atoms. It is one of the most important cannabinoids, a class of chemicals associated with the cannabis plant.[2] In nature, THC has high UV-B absorption ability and protects the cannabis plant from damaging radiation. These belong to a broader family of chemicals known as terpenoids, a class of plant chemical products.[1] THC readily degrades in acid solutions, and 2800 mg will dissolve in one liter of water at 23 degrees Celcius. There are four different varieties, or stereoisomers, of the tetrahydrocannabinol molecule.[3] Only one, however, occurs naturally, the (–)-trans isomer. The (-)-trans isomer is roughly 10-15 times more neurologically stimulating than its (+)-trans isomer.[2] THC is a glassy solid at colder temperatures and a syrup-like substance when warmed. The smoke produced after THC evaporates has a distinct sweet and sour aroma.[1]

THC is a light yellow oil that has a boiling point of 157 degrees celcius. When heated enough to degrade molecular bonds, THC emits acrid smoke and irritating fumes.[3] When ingested and eventually transported to the brain, these THC molecules bind to receptors called cannabinoid receptors, which are also found in lesser concentrations in nerves. These receptors determine thought, coordination, memory, pleasure, and perception of time.[4] Normally these receptors are stimulated by chemicals naturally found in the brain called anandamide, which has a very similar molecular structure as THC. This "lock and key" system stimulates the body's cells to release dopamine, often resulting in increased euphoria and temporary pain relief.[5]

Occurrences

THC is extracted from the plant Cannabis sativa L.
HU-210 is a synthetic cannabinoid receptor antagonist similar to THC used in "spice," a synthetic marijuana-like drug.

Tetrahydrocannabinol (THC) was first isolated in Rehovot, Israel in 1964 by Raphael Mechoulam, Yechiel Gaoni, and Habib Edery from the Weizmann Institute.[1] THC occurs naturally in the cannabis plant of two species, Cannabis Sativa Sativa and Cannabis Sativa Indica.[5] Naturally, THC occurs as tetrahydrocannabinol carboxylic acid (THC-COOH). Enzymatic reactions in the cannabis plant fuse geranyl pyrophosphate and olivetolic acid to form cannabigerolic acid. This resulting acid is cyclized by the enzyme THC acid synthase in the plant to produce this tetrahydrocannabinol carboxylic acid.

The extraction process for this oily substance relies upon its solubility in solvents other than water. Often cannabis leaves are dissolved in butane or isopropyl alcohol and the larger solid parts are strained out. The remaining solution is then purged of all solvents, leaving only THC-COOH and other minor ingredients found in cannabis.[6] When heated, the acid decarboxylates into THC.[3]


Uses

This drop of "hash oil" is composed primarily of THC and similar cannabis extracts.

THC has several uses and a variety of ingestion methods. Many use THC as a drug to increase euphoria, giving them a "high" that will inhibit their coordination and motor skills while often producing fantastical hallucinations and a sense of universal relaxation. Additionally, users report heightened sensory experiences of taste, sound, and vision.[2] These effects last for around two hours and will begin 10-30 minutes after ingestion. Impairment of psychomotor skills may continue even after the elevated euphoria has passed. However, overdosing on THC may cause the user to experience severe depression, anxiety, paranoia, and/or an unrealistic sense of imminent danger. THC is most often taken by burning and inhaling fumes from the cannabis plant. These fumes rapidly enter the bloodstream from the lungs, which soon introduces the chemical into the brain and other regions of the nervous system.[4] THC has not been scientifically determined to be addictive and has no withdrawal symptoms when taken by itself.[2] Still, tetrahydrocannabinol remains a Schedule 1 drug in the United States, meaning it has a high potential for abuse and retains a lack of accepted safety for use even under medical supervision.[7]


THC has several medical uses and is legal in several states as a medical drug. The molecule can be extracted from cannabis plants and sold as the drug marinol and dronabinol, taken orally by capsule. This is an FDA-approved drug and is used to remedy nausea, prevent vomiting associated with chemotherapy, and increase the appetites of those with AIDS.[3] It may also be used to treat asthma, Alzeitmers, and epilepsy.[1] Side effects include possible seizures or changes in mood. Additionally, THC is used to treat anorexia and other eating disorders, as appetite is safely increased as the regurgitation reaction is inhibited. However, THC often results in dramatically increased heart rate, giving users up to 4.8-fold increase in heart attack risk.[5]

Synthetic THC

Main Article: Synthetic cannabis
Synthetic substitutes for THC can be extremely dangerous.

The effects of THC can be mimicked by spraying herbs and plant materials with several possible psychoactive chemicals and sold as spice, K2, Skunk, or Yucatan Fire.[5] These cannabinoid receptor antagonists still retain the structure necessary for neurological stimulation, but may include dangerous chemicals like naphthoylindoles and cyclohexylphenols.[8] This synthetic THC was extremely popular with teenagers and young adults due to advertizing as "safe" and powerful. In addition, manufacturers label the spice packets with "not for human consumption" in order to circumvent laws regarding potent drugs.[5] However, the lack of quality control and regulation of synthetic THC has lead to potential unforeseen health risks; hospitalization for heart failure and seizures are much more common in synthetic THC than natural THC.

In 2012, the United States banned all sale of synthetic cannabinoids for their severe toxicity.[8] Some users have reported seizures, involuntary muscle spasms, and extreme psychological changes during the high.[9]

References

  1. 1.0 1.1 1.2 1.3 1.4 THC World of Molecules. Web. Accessed 13 January 2015.
  2. 2.0 2.1 2.2 2.3 Tetrahydrocannabinol Ch.Ic.Ac.Uk.. Web. Accessed 13 January 2015.
  3. 3.0 3.1 3.2 3.3 Dronabinol PubChem. Web. Accessed 13 January 2015.
  4. 4.0 4.1 Cox, Lauren. What is THC? Live Science. Web. Published 23 July 2014.
  5. 5.0 5.1 5.2 5.3 5.4 Drug FActs: Marijuana National Institute on Drug Abuse. Web. Updated January 2014.
  6. Extraction CannLabs. Web. Accessed 27 January 2015.
  7. List of Schedule 1 Drugs Drugs.com. Web. Updated 4 December 2014.
  8. 8.0 8.1 Synthetic Cannabinoids EMCDDA. Web. Updated 8 January 2015.
  9. Rael, Andrea. Synthetic Marajuana Huffington Post. Web. Updated 11 September 2013.