Tetrahydrocannabinol

Introduction to Tetrahydrocannabinol


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Using Tetrahydrocannabinol


THC is generally used as cannabis or some cannabis-derived preparation (hashish, space cakes, etc). THC, in its synthetic form (Dronabinol) to be used orally, is also available in some countries.

Ways of Administration


THC, when derived from a natural source can be smoked, vaporized or ingested as cannabis and related preparations.

Synthetic THC is available for oral administration. In some studies, THC is administered intravenously.

Effects of Tetrahydrocannabinol


The effects of THC are similar to those of cannabis, although some differences exist.

Objective effects


- Reduced intraocular pressure


Subjective effects


- Increased appetite

Combinations with Tetrahydrocannabinol


THC is usually combined to the other cannabinoids found in cannabis. The combinations are the same as those of cannabis.

Different Uses for Tetrahydrocannabinol


Therapeutic


THC, as Dronabinol, is used to increase appetite of aids patients.

Pharmacology of Tetrahydrocannabinol


LD50 (mg/kg) (sesame oil emulsion of ∆9-THC)[1] :
Male rat : 800 orally, 672 intraperitoneally, 35.5 intravenously

LD50 (mg/kg) (∆8-THC)[1]:
Mice : 27.5 intravenously

Chemistry of Tetrahydrocannabinol

From a chemical point of view, THC consist of seven isomers, depending on the position of the insaturation on the "upper" ring consisting of the carbons 6a-7-8-9-10-10a.

Column 1 Column 2
Title compound 9-THC
Systematic (IUPAC) name: (−)-(6aR,10aR)-6,6,9-Trimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromen-1-ol
Synonyms: (6aR,10aR)-6a,7,8,10a-tetrahydro-3-pentyl-6H-dibenzo[b,d]pyran-1-ol, (–)-∆1-3,4-trans-tetrahydrocannabinol, ∆9-THC, ∆1-THC, dronabinol, QCD-84924, Marinol
Molecular Formula: C21H30O2
Molar mass: 314.46 g/mol[2]
CAS Registry Number: 1972-08-3
Melting Point: no data
Boiling Point: 200°C @ 0.02 mmHg[1], also reported 157°C[3]
Flash Point: no data
Solubility: Insoluble in water (0.0028 mg/mL[4]); Freely soluble in benzene and aromatic solvents, butane and other alkanes; Soluble in acetone, isopropanol, ethanol[1].
Additionnal data: pKa 10.6[1]
Notes: Aspect : light yellow resinous oil; hardens upon refrigeration[1]
Column 1 Column 2
Title compound 8-THC
Systematic (IUPAC) name: (−)-(6aR,10aR)-6,6,9-Trimethyl-3-pentyl-6a,7,10,10a-tetrahydro-6H-benzo[c]chromen-1-ol
Synonyms: (–)-∆6-3,4-trans-tetrahydrocannabinol, ∆8-THC, ∆6-THC
Molecular Formula: C21H30O2
Molar mass: 314.46 g/mol[2]
CAS Registry Number: 5957-75-5
Melting Point: no data
Boiling Point: 200°C @ 0.001 mmHg[1]
Flash Point: no data
Solubility: no data
Additionnal data: none
Notes: none
Apart from the aforementionned positionnal isomers, 4 stereoisomers exists depending on the absolute configuration of the 6a and 10a carbons.
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The Dangers of Tetrahydrocannabinol


Physical Health Risks

<Physical Problem 1 - Please Identify and Add Others As Necessary>

<Physical Problem 2 - Please Identify and Add Others As Necessary>


Overdose


Reported Deaths


Mental Health Risks

<Mental Health Risk 1 - Please Identify and Add Others As Necessary>

<Mental Health Risk 2 - Please Identify and Add Others As Necessary>


Side Effects


Addiction


Physical Addiction

Mental Addiction


Producing Tetrahydrocannabinol


Tetrahydrocannabinol is produced via cannabis cultivation followed by extraction.

Biosynthesis of Tetrahydrocannabinol


Forms of Tetrahydrocannabinol



Tetrahydrocannabinol is a controlled substance 21 CFR 1308.11

United Nations


USA


EU


Other Countries


History of Tetrahydrocannabinol


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References

  1. ^ a b c d e f gMerck Index, fifteenth edition (2013)
  2. ^ a bCalculated from Atomic Weights of the Elements, 2007
  3. ^John M. McPartland, Ethan B. Russo; Cannabis and Cannabis Extracts: Greater Than the Sum of Their Parts? (2001)
  4. ^Garrett, Edward R.; Hunt, C. Anthony (July 1974). "Physicochemical properties, solubility, and protein binding of Δ9-tetrahydrocannabinol". J. Pharm. Sci. 63 (7): 1056–64.

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