Tetrahydro Cannabinol

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Tetrahydrocannabinol

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"THC" redirects here. For other uses, seeTHC(disambiguation).

Tetrahydrocannabinol

Systematic (IUPAC) name

()-(6aR,10aR)-6,6,9-trimethyl-

3-pentyl-6a,7,8,10a-tetrahydro-

6H-benzo[c]chromen-1-ol

Clinical data

Pregnancy cat. C

Legal statusControlled (S8)(AU)Schedule II(CA)

(CA)Schedule I and III(US)

Dependence liability 810%[1]

Routes orally, smoked (or vaporized)

Pharmacokinetic data

Bioavailability 1035% (inhalation), 620% (oral)[2]

Protein binding 9599%[2]

Metabolism mostly hepatic by CYP2C[2]

Half-life1.659 h,[2]2536 h (orally

administered dronabinol)

Excretion6580% (feces), 2035% (urine) as

acid metabolites[2]

Identifiers

CAS number 1972-08-3
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ATC code A04AD10

PubChem CID 16078

IUPHAR ligand 2424

DrugBank DB00470

ChemSpider 15266

UNII 7J8897W37S

ChEBI CHEBI:66964

ChEMBL CHEMBL465

Synonyms Dronabinol

Chemical data

Formula C21H30O2

Mol. mass 314.4636

SMILES[show]

InChI[show]

Physical data

Boiling point 157 C (315 F)[4]

Solubilityinwater 0.0028[3]

(23 C) mg/mL (20 C)

Spec. rot -152 (ethanol)

(what is this?) (verify)

Tetrahydrocannabinol (/ttrhadrknbnl/tet-r-HY-dr-k-NAB-i-nawlor

/ttrhadrknbnl/tet-r-HY-dr-k-NAB-i-nol;[5]THC), or more precisely its main isomer ()-trans-

9-tetrahydrocannabinol ((6aR,10aR)-delta-9-tetrahydrocannabinol), is the principal

psychoactiveconstituent (orcannabinoid) of thecannabisplant. First isolated in 1964, in its pure

form, byIsraeliscientistsRaphael Mechoulam,Yechiel Gaoniand colleagues at the Hebrew

University of Jerusalem,[6][7][8]

it is a glassy solid when cold, and becomesviscousand sticky if

warmed. Apharmaceutical formulationof ()-trans-9-tetrahydrocannabinol, known by itsINN

dronabinol, is available by prescription in the U.S. and Canada under the brand nameMarinol. An

aromaticterpenoid, THC has a very low solubility in water, but good solubility in most organic

solvents, specificallylipidsandalcohols.[3]

Like most pharmacologically-activesecondary metabolitesof plants, THC incannabisis assumed to

be involved inself-defense, perhaps againstherbivores.

[9]

THC also possesses highUV-B(280
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315 nm) absorption properties, which, it has been speculated, could protect the plant from harmful

UV radiation exposure.[10][11][12]

Tetrahydrocannabinol with double bond isomers and their stereoisomers is one of only three

cannabinoids scheduled byConvention on Psychotropic Substances(the other two are

dimethylheptylpyranandparahexyl). Note that cannabis as a plant is scheduled bySingle Convention

on Narcotic Drugs(Schedule I and IV).

Contents

1 Pharmacologyo 1.1 Effects

1.1.1 Appetite and tasteo 1.2 Antagonism

2 Isomerism 3 Toxicity 4 Research

o 4.1 Studies in humanso 4.2 Studies in animals and in vitroo 4.3 Scientific studies indicating side-effectso 4.4 Opinions and statistical observations indicating side-effects

5 Biosynthesiso 5.1 Natural occurrence

6 Metabolismo 6.1 Detection in body fluids

7 Marinolo 7.1 Comparisons to medical marijuana

8 Regulatory history 9 See also 10 References 11 Further reading 12 External links

Pharmacology

Thepharmacologicalactions of THC result from its partialagonistactivity at thecannabinoid receptorCB1(Ki=10nM

[13]), located mainly in thecentral nervous system, and theCB2receptor (Ki=24nM

[14]),
http://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-Pate1983-10http://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-Pate1983-10http://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-Lydon1987b-12http://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-Lydon1987b-12http://en.wikipedia.org/wiki/Convention_on_Psychotropic_Substanceshttp://en.wikipedia.org/wiki/Convention_on_Psychotropic_Substanceshttp://en.wikipedia.org/wiki/Convention_on_Psychotropic_Substanceshttp://en.wikipedia.org/wiki/Dimethylheptylpyranhttp://en.wikipedia.org/wiki/Dimethylheptylpyranhttp://en.wikipedia.org/wiki/Parahexylhttp://en.wikipedia.org/wiki/Parahexylhttp://en.wikipedia.org/wiki/Parahexylhttp://en.wikipedia.org/wiki/Single_Convention_on_Narcotic_Drugshttp://en.wikipedia.org/wiki/Single_Convention_on_Narcotic_Drugshttp://en.wikipedia.org/wiki/Single_Convention_on_Narcotic_Drugshttp://en.wikipedia.org/wiki/Single_Convention_on_Narcotic_Drugshttp://en.wikipedia.org/wiki/Tetrahydrocannabinol#Pharmacologyhttp://en.wikipedia.org/wiki/Tetrahydrocannabinol#Pharmacologyhttp://en.wikipedia.org/wiki/Tetrahydrocannabinol#Effectshttp://en.wikipedia.org/wiki/Tetrahydrocannabinol#Effectshttp://en.wikipedia.org/wiki/Tetrahydrocannabinol#Appetite_and_tastehttp://en.wikipedia.org/wiki/Tetrahydrocannabinol#Appetite_and_tastehttp://en.wikipedia.org/wiki/Tetrahydrocannabinol#Antagonismhttp://en.wikipedia.org/wiki/Tetrahydrocannabinol#Antagonismhttp://en.wikipedia.org/wiki/Tetrahydrocannabinol#Isomerismhttp://en.wikipedia.org/wiki/Tetrahydrocannabinol#Isomerismhttp://en.wikipedia.org/wiki/Tetrahydrocannabinol#Toxicityhttp://en.wikipedia.org/wiki/Tetrahydrocannabinol#Toxicityhttp://en.wikipedia.org/wiki/Tetrahydrocannabinol#Researchhttp://en.wikipedia.org/wiki/Tetrahydrocannabinol#Researchhttp://en.wikipedia.org/wiki/Tetrahydrocannabinol#Studies_in_humanshttp://en.wikipedia.org/wiki/Tetrahydrocannabinol#Studies_in_humanshttp://en.wikipedia.org/wiki/Tetrahydrocannabinol#Studies_in_animals_and_in_vitrohttp://en.wikipedia.org/wiki/Tetrahydrocannabinol#Studies_in_animals_and_in_vitrohttp://en.wikipedia.org/wiki/Tetrahydrocannabinol#Scientific_studies_indicating_side-effectshttp://en.wikipedia.org/wiki/Tetrahydrocannabinol#Scientific_studies_indicating_side-effectshttp://en.wikipedia.org/wiki/Tetrahydrocannabinol#Opinions_and_statistical_observations_indicating_side-effectshttp://en.wikipedia.org/wiki/Tetrahydrocannabinol#Opinions_and_statistical_observations_indicating_side-effectshttp://en.wikipedia.org/wiki/Tetrahydrocannabinol#Biosynthesishttp://en.wikipedia.org/wiki/Tetrahydrocannabinol#Biosynthesishttp://en.wikipedia.org/wiki/Tetrahydrocannabinol#Natural_occurrencehttp://en.wikipedia.org/wiki/Tetrahydrocannabinol#Natural_occurrencehttp://en.wikipedia.org/wiki/Tetrahydrocannabinol#Metabolismhttp://en.wikipedia.org/wiki/Tetrahydrocannabinol#Metabolismhttp://en.wikipedia.org/wiki/Tetrahydrocannabinol#Detection_in_body_fluidshttp://en.wikipedia.org/wiki/Tetrahydrocannabinol#Detection_in_body_fluidshttp://en.wikipedia.org/wiki/Tetrahydrocannabinol#Marinolhttp://en.wikipedia.org/wiki/Tetrahydrocannabinol#Marinolhttp://en.wikipedia.org/wiki/Tetrahydrocannabinol#Comparisons_to_medical_marijuanahttp://en.wikipedia.org/wiki/Tetrahydrocannabinol#Comparisons_to_medical_marijuanahttp://en.wikipedia.org/wiki/Tetrahydrocannabinol#Regulatory_historyhttp://en.wikipedia.org/wiki/Tetrahydrocannabinol#Regulatory_historyhttp://en.wikipedia.org/wiki/Tetrahydrocannabinol#See_alsohttp://en.wikipedia.org/wiki/Tetrahydrocannabinol#See_alsohttp://en.wikipedia.org/wiki/Tetrahydrocannabinol#Referenceshttp://en.wikipedia.org/wiki/Tetrahydrocannabinol#Referenceshttp://en.wikipedia.org/wiki/Tetrahydrocannabinol#Further_readinghttp://en.wikipedia.org/wiki/Tetrahydrocannabinol#Further_readinghttp://en.wikipedia.org/wiki/Tetrahydrocannabinol#External_linkshttp://en.wikipedia.org/wiki/Tetrahydrocannabinol#External_linkshttp://en.wikipedia.org/wiki/Pharmacologyhttp://en.wikipedia.org/wiki/Pharmacologyhttp://en.wikipedia.org/wiki/Pharmacologyhttp://en.wikipedia.org/wiki/Agonisthttp://en.wikipedia.org/wiki/Agonisthttp://en.wikipedia.org/wiki/Agonisthttp://en.wikipedia.org/wiki/Cannabinoid_receptorhttp://en.wikipedia.org/wiki/Cannabinoid_receptorhttp://en.wikipedia.org/wiki/Cannabinoid_receptorhttp://en.wikipedia.org/wiki/Cannabinoid_receptor_type_1http://en.wikipedia.org/wiki/Cannabinoid_receptor_type_1http://en.wikipedia.org/wiki/Cannabinoid_receptor_type_1http://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-13http://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-13http://en.wikipedia.org/wiki/Central_nervous_systemhttp://en.wikipedia.org/wiki/Central_nervous_systemhttp://en.wikipedia.org/wiki/Central_nervous_systemhttp://en.wikipedia.org/wiki/Cannabinoid_receptor_type_2http://en.wikipedia.org/wiki/Cannabinoid_receptor_type_2http://en.wikipedia.org/wiki/Cannabinoid_receptor_type_2http://en.wikipedia.org/wiki/Cannabinoid_receptor_type_2http://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-14http://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-14http://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-14http://en.wikipedia.org/wiki/Cannabinoid_receptor_type_2http://en.wikipedia.org/wiki/Central_nervous_systemhttp://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-13http://en.wikipedia.org/wiki/Cannabinoid_receptor_type_1http://en.wikipedia.org/wiki/Cannabinoid_receptorhttp://en.wikipedia.org/wiki/Agonisthttp://en.wikipedia.org/wiki/Pharmacologyhttp://en.wikipedia.org/wiki/Tetrahydrocannabinol#External_linkshttp://en.wikipedia.org/wiki/Tetrahydrocannabinol#Further_readinghttp://en.wikipedia.org/wiki/Tetrahydrocannabinol#Referenceshttp://en.wikipedia.org/wiki/Tetrahydrocannabinol#See_alsohttp://en.wikipedia.org/wiki/Tetrahydrocannabinol#Regulatory_historyhttp://en.wikipedia.org/wiki/Tetrahydrocannabinol#Comparisons_to_medical_marijuanahttp://en.wikipedia.org/wiki/Tetrahydrocannabinol#Marinolhttp://en.wikipedia.org/wiki/Tetrahydrocannabinol#Detection_in_body_fluidshttp://en.wikipedia.org/wiki/Tetrahydrocannabinol#Metabolismhttp://en.wikipedia.org/wiki/Tetrahydrocannabinol#Natural_occurrencehttp://en.wikipedia.org/wiki/Tetrahydrocannabinol#Biosynthesishttp://en.wikipedia.org/wiki/Tetrahydrocannabinol#Opinions_and_statistical_observations_indicating_side-effectshttp://en.wikipedia.org/wiki/Tetrahydrocannabinol#Scientific_studies_indicating_side-effectshttp://en.wikipedia.org/wiki/Tetrahydrocannabinol#Studies_in_animals_and_in_vitrohttp://en.wikipedia.org/wiki/Tetrahydrocannabinol#Studies_in_humanshttp://en.wikipedia.org/wiki/Tetrahydrocannabinol#Researchhttp://en.wikipedia.org/wiki/Tetrahydrocannabinol#Toxicityhttp://en.wikipedia.org/wiki/Tetrahydrocannabinol#Isomerismhttp://en.wikipedia.org/wiki/Tetrahydrocannabinol#Antagonismhttp://en.wikipedia.org/wiki/Tetrahydrocannabinol#Appetite_and_tastehttp://en.wikipedia.org/wiki/Tetrahydrocannabinol#Effectshttp://en.wikipedia.org/wiki/Tetrahydrocannabinol#Pharmacologyhttp://en.wikipedia.org/wiki/Single_Convention_on_Narcotic_Drugshttp://en.wikipedia.org/wiki/Single_Convention_on_Narcotic_Drugshttp://en.wikipedia.org/wiki/Parahexylhttp://en.wikipedia.org/wiki/Dimethylheptylpyranhttp://en.wikipedia.org/wiki/Convention_on_Psychotropic_Substanceshttp://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-Lydon1987b-12http://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-Pate1983-10http://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-Pate1983-10


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mainly expressed in cells of theimmune system.[15]

The psychoactive effects of THC are primarily

mediated by its activation of CB1G-protein coupled receptors, which result in a decrease in the

concentration of the second messenger moleculecAMPthrough inhibition ofadenylate cyclase.[16]

The presence of these specialized cannabinoid receptors in thebrainled researchers to the discovery

ofendocannabinoids, such asanandamideand 2-arachidonoyl glyceride (2-AG). THC targets

receptors in a manner far less selective than endocannabinoid molecules released duringretrograde

signaling, as the drug has a relatively low cannabinoid receptor efficacy and affinity. In populations of

low cannabinoid receptor density, THC may act to antagonize endogenous agonists that possess

greater receptor efficacy.[17]

THC is alipophilicmolecule and may bind non-specifically to a variety of

receptors in the brain and body, such asadipose tissue. For a review of the mechanisms behind

endocannabinoid synaptic transmission, see theendocannabinoid system.

Several studies have suggested that THC also has ananticholinesteraseaction[18][19]

which may

implicate it as a potential treatment forAlzheimer'sandMyasthenia Gravis.

Effects

THC has mild to moderateanalgesiceffects, andcannabiscan be used to treat pain by altering

transmitter release ondorsal root ganglionof thespinal cordand in theperiaqueductal gray.[16]

Other effects include relaxation, alteration of visual, auditory, and olfactory senses, fatigue, and

appetite stimulation. THC has markedantiemeticproperties, and may also reduce aggression in

certain subjects.[20]

Due to its partial agonistic activity, THC appears to result in greaterdownregulationof cannabinoid

receptors than endocannabinoids, further limiting its efficacy over other cannabinoids. While

tolerance may limit the maximal effects of certain drugs, evidence suggests that tolerance develops

irregularly for different effects with greater resistance for primary over side-effects, and may actually

serve to enhance the drug's therapeutic window.[17]

However, this form of tolerance appears to be

irregular throughout mouse brain areas and warrants future research.

THC reduces mouse male fertilityin vivo, by inhibitingATPproduction insperm.[21]

THC, as well as other cannabinoids that contain a phenol group, possesses mildantioxidantactivity

sufficient to protect neurons against oxidative stress, such as that produced by glutamate-induced

excitotoxicity.[15]

Appetite and taste

It has long been known that, in humans, cannabis increases appetite and consumption of food. The

mechanism for appetite stimulation in subjects is believed to result from activity in the gastro-

hypothalamic axis. CB1 activity in the hunger centers in the hypothalamus increases the palatabilityof food when levels of a hunger hormoneghrelinincrease prior to consuming a meal. Afterchymeis

passed into theduodenum, signalinghormonessuch ascholecystokininandleptinare released,

causing reduction in gastric emptying and transmission of satiety signals to the hypothalamus.

Cannabinoid activity is reduced through the satiety signals induced by leptin release.

Based on the connection between palatable food and stimulation ofdopamine(DA) transmission in

the shell of thenucleus accumbens(NAc), it has been suggested that cannabis does not only

stimulate taste, but possibly the hedonic value of food. A taste-reactivity paradigm in mice was used

to investigate the influence of THC on DA release in the NAc upon application of sucrose orquinine

solutions. THC application was found to enhance DA release in the NAc from sucrose, but not

quinine, in a dose-dependent manner. This effect was enhanced with sweeter solution, whichcorrelated with an increase the researchers' hedonic-behavior assessment as well. The mechanism
http://en.wikipedia.org/wiki/Immune_systemhttp://en.wikipedia.org/wiki/Immune_systemhttp://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-pmid16570099-15http://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-pmid16570099-15http://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-pmid16570099-15http://en.wikipedia.org/wiki/G-protein_coupled_receptorhttp://en.wikipedia.org/wiki/G-protein_coupled_receptorhttp://en.wikipedia.org/wiki/G-protein_coupled_receptorhttp://en.wikipedia.org/wiki/Cyclic_adenosine_monophosphatehttp://en.wikipedia.org/wiki/Cyclic_adenosine_monophosphatehttp://en.wikipedia.org/wiki/Cyclic_adenosine_monophosphatehttp://en.wikipedia.org/wiki/Adenylate_cyclasehttp://en.wikipedia.org/wiki/Adenylate_cyclasehttp://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-pmid11316486-16http://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-pmid11316486-16http://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-pmid11316486-16http://en.wikipedia.org/wiki/Brainhttp://en.wikipedia.org/wiki/Brainhttp://en.wikipedia.org/wiki/Brainhttp://en.wikipedia.org/wiki/Endocannabinoidshttp://en.wikipedia.org/wiki/Endocannabinoidshttp://en.wikipedia.org/wiki/Endocannabinoidshttp://en.wikipedia.org/wiki/Anandamidehttp://en.wikipedia.org/wiki/Anandamidehttp://en.wikipedia.org/wiki/Anandamidehttp://en.wikipedia.org/wiki/2-AGhttp://en.wikipedia.org/wiki/2-AGhttp://en.wikipedia.org/wiki/2-AGhttp://en.wikipedia.org/wiki/Retrograde_signalinghttp://en.wikipedia.org/wiki/Retrograde_signalinghttp://en.wikipedia.org/wiki/Retrograde_signalinghttp://en.wikipedia.org/wiki/Retrograde_signalinghttp://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-pmid17828291-17http://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-pmid17828291-17http://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-pmid17828291-17http://en.wikipedia.org/wiki/Lipophilichttp://en.wikipedia.org/wiki/Lipophilichttp://en.wikipedia.org/wiki/Lipophilichttp://en.wikipedia.org/wiki/Adipose_tissuehttp://en.wikipedia.org/wiki/Adipose_tissuehttp://en.wikipedia.org/wiki/Adipose_tissuehttp://en.wikipedia.org/wiki/Endocannabinoid_systemhttp://en.wikipedia.org/wiki/Endocannabinoid_systemhttp://en.wikipedia.org/wiki/Endocannabinoid_systemhttp://en.wikipedia.org/wiki/Anticholinesterasehttp://en.wikipedia.org/wiki/Anticholinesterasehttp://en.wikipedia.org/wiki/Anticholinesterasehttp://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-18http://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-18http://en.wikipedia.org/wiki/Alzheimer%27shttp://en.wikipedia.org/wiki/Alzheimer%27shttp://en.wikipedia.org/wiki/Alzheimer%27shttp://en.wikipedia.org/wiki/Myasthenia_Gravishttp://en.wikipedia.org/wiki/Myasthenia_Gravishttp://en.wikipedia.org/wiki/Myasthenia_Gravishttp://en.wikipedia.org/wiki/Analgesichttp://en.wikipedia.org/wiki/Analgesichttp://en.wikipedia.org/wiki/Analgesichttp://en.wikipedia.org/wiki/Cannabishttp://en.wikipedia.org/wiki/Cannabishttp://en.wikipedia.org/wiki/Cannabishttp://en.wikipedia.org/wiki/Dorsal_root_ganglionhttp://en.wikipedia.org/wiki/Dorsal_root_ganglionhttp://en.wikipedia.org/wiki/Dorsal_root_ganglionhttp://en.wikipedia.org/wiki/Spinal_cordhttp://en.wikipedia.org/wiki/Spinal_cordhttp://en.wikipedia.org/wiki/Spinal_cordhttp://en.wikipedia.org/wiki/Periaqueductal_grayhttp://en.wikipedia.org/wiki/Periaqueductal_grayhttp://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-pmid11316486-16http://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-pmid11316486-16http://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-pmid11316486-16http://en.wikipedia.org/wiki/Antiemetichttp://en.wikipedia.org/wiki/Antiemetichttp://en.wikipedia.org/wiki/Antiemetichttp://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-20http://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-20http://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-20http://en.wikipedia.org/wiki/Downregulationhttp://en.wikipedia.org/wiki/Downregulationhttp://en.wikipedia.org/wiki/Downregulationhttp://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-pmid17828291-17http://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-pmid17828291-17http://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-pmid17828291-17http://en.wikipedia.org/wiki/In_vivohttp://en.wikipedia.org/wiki/In_vivohttp://en.wikipedia.org/wiki/In_vivohttp://en.wikipedia.org/wiki/Adenosine_triphosphatehttp://en.wikipedia.org/wiki/Adenosine_triphosphatehttp://en.wikipedia.org/wiki/Adenosine_triphosphatehttp://en.wikipedia.org/wiki/Spermhttp://en.wikipedia.org/wiki/Spermhttp://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-21http://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-21http://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-21http://en.wikipedia.org/wiki/Antioxidanthttp://en.wikipedia.org/wiki/Antioxidanthttp://en.wikipedia.org/wiki/Antioxidanthttp://en.wikipedia.org/wiki/Excitotoxicityhttp://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-pmid16570099-15http://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-pmid16570099-15http://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-pmid16570099-15http://en.wikipedia.org/wiki/Ghrelinhttp://en.wikipedia.org/wiki/Ghrelinhttp://en.wikipedia.org/wiki/Ghrelinhttp://en.wikipedia.org/wiki/Chymehttp://en.wikipedia.org/wiki/Chymehttp://en.wikipedia.org/wiki/Chymehttp://en.wikipedia.org/wiki/Duodenumhttp://en.wikipedia.org/wiki/Duodenumhttp://en.wikipedia.org/wiki/Duodenumhttp://en.wikipedia.org/wiki/Hormonehttp://en.wikipedia.org/wiki/Hormonehttp://en.wikipedia.org/wiki/Hormonehttp://en.wikipedia.org/wiki/Cholecystokininhttp://en.wikipedia.org/wiki/Cholecystokininhttp://en.wikipedia.org/wiki/Cholecystokininhttp://en.wikipedia.org/wiki/Leptinhttp://en.wikipedia.org/wiki/Leptinhttp://en.wikipedia.org/wiki/Leptinhttp://en.wikipedia.org/wiki/Dopaminehttp://en.wikipedia.org/wiki/Dopaminehttp://en.wikipedia.org/wiki/Dopaminehttp://en.wikipedia.org/wiki/Nucleus_accumbenshttp://en.wikipedia.org/wiki/Nucleus_accumbenshttp://en.wikipedia.org/wiki/Nucleus_accumbenshttp://en.wikipedia.org/wiki/Quininehttp://en.wikipedia.org/wiki/Quininehttp://en.wikipedia.org/wiki/Quininehttp://en.wikipedia.org/wiki/Quininehttp://en.wikipedia.org/wiki/Nucleus_accumbenshttp://en.wikipedia.org/wiki/Dopaminehttp://en.wikipedia.org/wiki/Leptinhttp://en.wikipedia.org/wiki/Cholecystokininhttp://en.wikipedia.org/wiki/Hormonehttp://en.wikipedia.org/wiki/Duodenumhttp://en.wikipedia.org/wiki/Chymehttp://en.wikipedia.org/wiki/Ghrelinhttp://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-pmid16570099-15http://en.wikipedia.org/wiki/Excitotoxicityhttp://en.wikipedia.org/wiki/Antioxidanthttp://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-21http://en.wikipedia.org/wiki/Spermhttp://en.wikipedia.org/wiki/Adenosine_triphosphatehttp://en.wikipedia.org/wiki/In_vivohttp://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-pmid17828291-17http://en.wikipedia.org/wiki/Downregulationhttp://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-20http://en.wikipedia.org/wiki/Antiemetichttp://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-pmid11316486-16http://en.wikipedia.org/wiki/Periaqueductal_grayhttp://en.wikipedia.org/wiki/Spinal_cordhttp://en.wikipedia.org/wiki/Dorsal_root_ganglionhttp://en.wikipedia.org/wiki/Cannabishttp://en.wikipedia.org/wiki/Analgesichttp://en.wikipedia.org/wiki/Myasthenia_Gravishttp://en.wikipedia.org/wiki/Alzheimer%27shttp://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-18http://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-18http://en.wikipedia.org/wiki/Anticholinesterasehttp://en.wikipedia.org/wiki/Endocannabinoid_systemhttp://en.wikipedia.org/wiki/Adipose_tissuehttp://en.wikipedia.org/wiki/Lipophilichttp://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-pmid17828291-17http://en.wikipedia.org/wiki/Retrograde_signalinghttp://en.wikipedia.org/wiki/Retrograde_signalinghttp://en.wikipedia.org/wiki/2-AGhttp://en.wikipedia.org/wiki/Anandamidehttp://en.wikipedia.org/wiki/Endocannabinoidshttp://en.wikipedia.org/wiki/Brainhttp://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-pmid11316486-16http://en.wikipedia.org/wiki/Adenylate_cyclasehttp://en.wikipedia.org/wiki/Cyclic_adenosine_monophosphatehttp://en.wikipedia.org/wiki/G-protein_coupled_receptorhttp://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-pmid16570099-15http://en.wikipedia.org/wiki/Immune_system


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behind this effect was elucidated by application ofrimonabant, a CB1 receptor inverse agonist,

known to reduce intake of food or sweet solutions. However, the same DA enhancement effect was

not found upon repeated application of sucrose, suggesting that the DA response undergoes

habituation.[22]

The inconsistency between DA habituation and enduring appetite observed after THC

application suggests that cannabis-induced appetite stimulation is not only mediated by enhanced

pleasure from platable food, but through THC stimulation of another appetitive response as well.

Antagonism

The effects of the drug can be suppressed by the CB1 receptor antagonistrimonabant(SR141716A) as

well asopioid receptorantagonists (opioid blockers)naloxoneandnaloxonazine.[23]

The 7 nicotinicreceptor antagonistmethyllycaconitinecan block self-administration of THC in rates comparable to

the effects ofvareniclineon nicotine administration.[24]

Isomerism

7 double bond isomers and their 30 stereoisomers

Dibenzopyran numbering

Monoterpenoid

numbering

Number

of

stereoiso

mers

Natura

l

occurr

ence

Convent

ion on

Psychot

ropic

Substan

ces

Schedul

e

Structure

Short name

Chir

al

cent

ers

Full name Short name

Chir

al

cent

ers

6a,7-

tetrahydrocannabinol

9

and10a

8,9,10,10a-

tetrahydro-

6,6,9-

trimethyl-3-pentyl-6H-

dibenzo[b,d]

pyran-1-ol

4-


1

and3

4 No Schedule I

7-

tetrahydrocan

nabinol

6a, 9

and

10a

6a,9,10,10a-

tetrahydro-

6,6,9-

trimethyl-3-

pentyl-6H-

dibenzo[b,d]

pyran-1-ol

5-

tetrahydrocan

nabinol

1, 3

and

4

8 NoSchedul

e I
http://en.wikipedia.org/wiki/Rimonabanthttp://en.wikipedia.org/wiki/Rimonabanthttp://en.wikipedia.org/wiki/Rimonabanthttp://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-22http://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-22http://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-22http://en.wikipedia.org/wiki/Rimonabanthttp://en.wikipedia.org/wiki/Rimonabanthttp://en.wikipedia.org/wiki/Rimonabanthttp://en.wikipedia.org/wiki/Opioid_receptorhttp://en.wikipedia.org/wiki/Opioid_receptorhttp://en.wikipedia.org/wiki/Opioid_receptorhttp://en.wikipedia.org/wiki/Naloxonehttp://en.wikipedia.org/wiki/Naloxonehttp://en.wikipedia.org/wiki/Naloxonehttp://en.wikipedia.org/wiki/Naloxonazinehttp://en.wikipedia.org/wiki/Naloxonazinehttp://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-Lupica_2004-23http://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-Lupica_2004-23http://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-Lupica_2004-23http://en.wikipedia.org/wiki/Methyllycaconitinehttp://en.wikipedia.org/wiki/Methyllycaconitinehttp://en.wikipedia.org/wiki/Methyllycaconitinehttp://en.wikipedia.org/wiki/Vareniclinehttp://en.wikipedia.org/wiki/Vareniclinehttp://en.wikipedia.org/wiki/Vareniclinehttp://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-24http://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-24http://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-24http://en.wikipedia.org/wiki/Convention_on_Psychotropic_Substanceshttp://en.wikipedia.org/wiki/Convention_on_Psychotropic_Substanceshttp://en.wikipedia.org/wiki/Convention_on_Psychotropic_Substanceshttp://en.wikipedia.org/wiki/Convention_on_Psychotropic_Substanceshttp://en.wikipedia.org/wiki/Convention_on_Psychotropic_Substanceshttp://en.wikipedia.org/wiki/Convention_on_Psychotropic_Substanceshttp://en.wikipedia.org/wiki/Convention_on_Psychotropic_Substanceshttp://en.wikipedia.org/wiki/File:Delta7-Tetrahydrocannabinol.pnghttp://en.wikipedia.org/wiki/File:Delta6a,7-Tetrahydrocannabinol.pnghttp://en.wikipedia.org/wiki/File:Dibenzopyran_and_monoterpenoid_numbering_of_tetrahydrocannabinol.pnghttp://en.wikipedia.org/wiki/File:Delta7-Tetrahydrocannabinol.pnghttp://en.wikipedia.org/wiki/File:Delta6a,7-Tetrahydrocannabinol.pnghttp://en.wikipedia.org/wiki/File:Dibenzopyran_and_monoterpenoid_numbering_of_tetrahydrocannabinol.pnghttp://en.wikipedia.org/wiki/File:Delta7-Tetrahydrocannabinol.pnghttp://en.wikipedia.org/wiki/File:Delta6a,7-Tetrahydrocannabinol.pnghttp://en.wikipedia.org/wiki/File:Dibenzopyran_and_monoterpenoid_numbering_of_tetrahydrocannabinol.pnghttp://en.wikipedia.org/wiki/Convention_on_Psychotropic_Substanceshttp://en.wikipedia.org/wiki/Convention_on_Psychotropic_Substanceshttp://en.wikipedia.org/wiki/Convention_on_Psychotropic_Substanceshttp://en.wikipedia.org/wiki/Convention_on_Psychotropic_Substanceshttp://en.wikipedia.org/wiki/Convention_on_Psychotropic_Substanceshttp://en.wikipedia.org/wiki/Convention_on_Psychotropic_Substanceshttp://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-24http://en.wikipedia.org/wiki/Vareniclinehttp://en.wikipedia.org/wiki/Methyllycaconitinehttp://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-Lupica_2004-23http://en.wikipedia.org/wiki/Naloxonazinehttp://en.wikipedia.org/wiki/Naloxonehttp://en.wikipedia.org/wiki/Opioid_receptorhttp://en.wikipedia.org/wiki/Rimonabanthttp://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-22http://en.wikipedia.org/wiki/Rimonabant


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8-tetrahydrocan

nabinol

6a

and

10a

6a,7,10,10a-

tetrahydro-

6,6,9-

trimethyl-3-

pentyl-6H-

dibenzo[b,d]pyran-1-ol

6-tetrahydrocan

nabinol

3

and

4

4 YesSchedul

e I

9,11-

tetrahydrocan

nabinol

6a

and

10a

6a,7,8,9,10,1

0a-

hexahydro-

6,6-

dimethyl-9-

methylene-

3-pentyl-6H-

dibenzo[b,d]

pyran-1-ol

1,7-

tetrahydrocan

nabinol

3

and

4

4 NoSchedul

e I

9-

tetrahydrocan

nabinol

6a

and

10a

6a,7,8,10a-

tetrahydro-

6,6,9-

trimethyl-3-

pentyl-6H-

dibenzo[b,d]

pyran-1-ol

1-

tetrahydrocan

nabinol

3

and

4

4 YesSchedul

e II

10-

tetrahydrocan

nabinol

6a

and

9

6a,7,8,9-

tetrahydro-

6,6,9-

trimethyl-3-

pentyl-6H-

dibenzo[b,d]

pyran-1-ol

2-

tetrahydrocan

nabinol

1

and

4

4 NoSchedul

e I

6a,10a-

tetrahydrocan

nabinol

9

7,8,9,10-

tetrahydro-

6,6,9-

trimethyl-3-

pentyl-6H-

dibenzo[b,d]

pyran-1-ol

3-

tetrahydrocan

nabinol

1 2 NoSchedul

e I

4 stereoisomers of 9-tetrahydrocannabinol

Names DescriptionNatural

occurrenceStructure

()-trans-9-


(6aR,10aR)-9-


levorotary

transYes

()-cis-9- (6aS,10aR)-9- levorotary Yes
http://en.wikipedia.org/wiki/File:Delta6a,10a-Tetrahydrocannabinol.pnghttp://en.wikipedia.org/wiki/File:Delta10-Tetrahydrocannabinol.pnghttp://en.wikipedia.org/wiki/File:Delta9-Tetrahydrocannabinol.pnghttp://en.wikipedia.org/wiki/File:Delta9,11-Tetrahydrocannabinol.pnghttp://en.wikipedia.org/wiki/File:Delta8-Tetrahydrocannabinol.pnghttp://en.wikipedia.org/wiki/File:Delta6a,10a-Tetrahydrocannabinol.pnghttp://en.wikipedia.org/wiki/File:Delta10-Tetrahydrocannabinol.pnghttp://en.wikipedia.org/wiki/File:Delta9-Tetrahydrocannabinol.pnghttp://en.wikipedia.org/wiki/File:Delta9,11-Tetrahydrocannabinol.pnghttp://en.wikipedia.org/wiki/File:Delta8-Tetrahydrocannabinol.pnghttp://en.wikipedia.org/wiki/File:Delta6a,10a-Tetrahydrocannabinol.pnghttp://en.wikipedia.org/wiki/File:Delta10-Tetrahydrocannabinol.pnghttp://en.wikipedia.org/wiki/File:Delta9-Tetrahydrocannabinol.pnghttp://en.wikipedia.org/wiki/File:Delta9,11-Tetrahydrocannabinol.pnghttp://en.wikipedia.org/wiki/File:Delta8-Tetrahydrocannabinol.pnghttp://en.wikipedia.org/wiki/File:Delta6a,10a-Tetrahydrocannabinol.pnghttp://en.wikipedia.org/wiki/File:Delta10-Tetrahydrocannabinol.pnghttp://en.wikipedia.org/wiki/File:Delta9-Tetrahydrocannabinol.pnghttp://en.wikipedia.org/wiki/File:Delta9,11-Tetrahydrocannabinol.pnghttp://en.wikipedia.org/wiki/File:Delta8-Tetrahydrocannabinol.pnghttp://en.wikipedia.org/wiki/File:Delta6a,10a-Tetrahydrocannabinol.pnghttp://en.wikipedia.org/wiki/File:Delta10-Tetrahydrocannabinol.pnghttp://en.wikipedia.org/wiki/File:Delta9-Tetrahydrocannabinol.pnghttp://en.wikipedia.org/wiki/File:Delta9,11-Tetrahydrocannabinol.pnghttp://en.wikipedia.org/wiki/File:Delta8-Tetrahydrocannabinol.png


7/14

tetrahydrocannabinol tetrahydrocannabinol cis

(+)-trans-9-


(6aS,10aS)-9-


dextrorotary

transNo

(+)-cis-9-


(6aR,10aS)-9-


dextrorotary

cisNo

Note that 6H-dibenzo[b,d]pyran-1-ol is the same as 6H-benzo[c]chromen-1-ol.

See also:Cannabidiol#Isomerism,John C. Leffingwell Chirality & Bioactivity I.: Pharmacology, 2003.

Toxicity

3D rendering of the THC molecule

A hybrid Cannabis strain (White Widow) flower coated withtrichomes, which contain more THC than

any other part of the plant
http://en.wikipedia.org/wiki/Cannabidiol#Isomerismhttp://en.wikipedia.org/wiki/Cannabidiol#Isomerismhttp://en.wikipedia.org/wiki/Cannabidiol#Isomerismhttp://www.leffingwell.com/download/chirality-phamacology.pdfhttp://www.leffingwell.com/download/chirality-phamacology.pdfhttp://www.leffingwell.com/download/chirality-phamacology.pdfhttp://www.leffingwell.com/download/chirality-phamacology.pdfhttp://www.leffingwell.com/download/chirality-phamacology.pdfhttp://en.wikipedia.org/wiki/White_widow_%28cannabis%29http://en.wikipedia.org/wiki/White_widow_%28cannabis%29http://en.wikipedia.org/wiki/White_widow_%28cannabis%29http://en.wikipedia.org/wiki/Trichomeshttp://en.wikipedia.org/wiki/Trichomeshttp://en.wikipedia.org/wiki/Trichomeshttp://en.wikipedia.org/wiki/File:White_widow.jpghttp://en.wikipedia.org/wiki/File:White_widow.jpghttp://en.wikipedia.org/wiki/File:Thc.pdb.gifhttp://en.wikipedia.org/wiki/File:Thc.pdb.gifhttp://en.wikipedia.org/wiki/File:(+)-(6aR,10aS)-%CE%949-Tetrahydrocannabinol_(with_hydrogen_atoms_shown).svghttp://en.wikipedia.org/wiki/File:(+)-(6aS,10aS)-%CE%949-Tetrahydrocannabinol_(with_hydrogen_atoms_shown).svghttp://en.wikipedia.org/wiki/File:White_widow.jpghttp://en.wikipedia.org/wiki/File:White_widow.jpghttp://en.wikipedia.org/wiki/File:Thc.pdb.gifhttp://en.wikipedia.org/wiki/File:Thc.pdb.gifhttp://en.wikipedia.org/wiki/File:(+)-(6aR,10aS)-%CE%949-Tetrahydrocannabinol_(with_hydrogen_atoms_shown).svghttp://en.wikipedia.org/wiki/File:(+)-(6aS,10aS)-%CE%949-Tetrahydrocannabinol_(with_hydrogen_atoms_shown).svghttp://en.wikipedia.org/wiki/File:White_widow.jpghttp://en.wikipedia.org/wiki/File:White_widow.jpghttp://en.wikipedia.org/wiki/File:Thc.pdb.gifhttp://en.wikipedia.org/wiki/File:Thc.pdb.gifhttp://en.wikipedia.org/wiki/File:(+)-(6aR,10aS)-%CE%949-Tetrahydrocannabinol_(with_hydrogen_atoms_shown).svghttp://en.wikipedia.org/wiki/File:(+)-(6aS,10aS)-%CE%949-Tetrahydrocannabinol_(with_hydrogen_atoms_shown).svghttp://en.wikipedia.org/wiki/File:White_widow.jpghttp://en.wikipedia.org/wiki/File:White_widow.jpghttp://en.wikipedia.org/wiki/File:Thc.pdb.gifhttp://en.wikipedia.org/wiki/File:Thc.pdb.gifhttp://en.wikipedia.org/wiki/File:(+)-(6aR,10aS)-%CE%949-Tetrahydrocannabinol_(with_hydrogen_atoms_shown).svghttp://en.wikipedia.org/wiki/File:(+)-(6aS,10aS)-%CE%949-Tetrahydrocannabinol_(with_hydrogen_atoms_shown).svghttp://en.wikipedia.org/wiki/File:White_widow.jpghttp://en.wikipedia.org/wiki/File:White_widow.jpghttp://en.wikipedia.org/wiki/File:Thc.pdb.gifhttp://en.wikipedia.org/wiki/File:Thc.pdb.gifhttp://en.wikipedia.org/wiki/File:(+)-(6aR,10aS)-%CE%949-Tetrahydrocannabinol_(with_hydrogen_atoms_shown).svghttp://en.wikipedia.org/wiki/File:(+)-(6aS,10aS)-%CE%949-Tetrahydrocannabinol_(with_hydrogen_atoms_shown).svghttp://en.wikipedia.org/wiki/File:White_widow.jpghttp://en.wikipedia.org/wiki/File:White_widow.jpghttp://en.wikipedia.org/wiki/File:Thc.pdb.gifhttp://en.wikipedia.org/wiki/File:Thc.pdb.gifhttp://en.wikipedia.org/wiki/File:(+)-(6aR,10aS)-%CE%949-Tetrahydrocannabinol_(with_hydrogen_atoms_shown).svghttp://en.wikipedia.org/wiki/File:(+)-(6aS,10aS)-%CE%949-Tetrahydrocannabinol_(with_hydrogen_atoms_shown).svghttp://en.wikipedia.org/wiki/Trichomeshttp://en.wikipedia.org/wiki/White_widow_%28cannabis%29http://www.leffingwell.com/download/chirality-phamacology.pdfhttp://en.wikipedia.org/wiki/Cannabidiol#Isomerism


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Closeup of THC-filled trichomes on a Cannabis sativa leaf

There has never been a documented human fatality solely from overdosing on tetrahydrocannabinol

or cannabis in its natural form,[25]

though the synthetic THC pill "Marinol" was cited by the FDA as

being responsible for 4 deaths between January 1, 1997 and June 30, 2005.

[26]

Information aboutTHC'stoxicityis primarily based on results from animal studies. The toxicity depends on the route of

administration and the laboratory animal. Absorption is limited byserum lipids, which can become

saturated with THC, mitigating toxicity.[27]

Research

The discovery of THC was first described in "Isolation, structure and partial synthesis of an active

constituent of hashish", published in theJournal of the American Chemical Societyin 1964.[6]

Research was also published in theacademic journalScience, with "Marijuana chemistry" byRaphael

Mechoulamin June 1970,[28]

followed by "Chemical basis of hashish activity" in August 1970.[29]

In the

latter, the team of researchers fromHebrew UniversityPharmacy School andTel Aviv University

Medical School experimented on monkeys to isolate the active compounds inhashish. Their resultsprovided evidence that, except for tetrahydrocannabinol, no other major active compounds were

present in hashish.

Studies in humans

Evidence suggests that THC helps alleviate symptoms suffered both byAIDSpatients, and by cancer

patients undergoingchemotherapy, by increasing appetite and decreasing nausea.[30][31][32][33]

It has

also been shown to assist someglaucomapatients by reducing pressure within the eye, and is used

in the form of cannabis by a number ofmultiple sclerosispatients, who use it to alleviateneuropathic

painandspasticity. TheNational Multiple Sclerosis Societyis currently supporting further research

into these uses.[34]

Studies in humans have been limited by federal and state laws criminalizing

marijuana.

In August 2009 aphase IV clinical trialby theHadassah Medical Centerin Jerusalem, Israel started to

investigate the effects of THC onpost-traumatic stress disorders.[35]

Dronabinol's usefulness as a treatment for Tourette syndrome cannot be determined until/unless

longer controlled studies on larger samples are undertaken.[36][37][38]

Research on THC has shown that thecannabinoid receptorsare responsible for mediated inhibition

of dopamine release in the retina.[39]

In a 1981 double-blind, placebo-controlled study, oral THC was given to Multiple Sclerosis patients. A

decrease in spasticity was shown when compared with placebo.[40]In a 1983 single-blind, placebo-

controlled study, decreased tremor occurred in 1/4 of Multiple Sclerosis patients.[41]
http://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-Walker_and_Huang-25http://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-Walker_and_Huang-25http://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-Walker_and_Huang-25http://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-26http://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-26http://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-26http://en.wikipedia.org/wiki/Toxicityhttp://en.wikipedia.org/wiki/Toxicityhttp://en.wikipedia.org/wiki/Toxicityhttp://en.wikipedia.org/wiki/Blood_lipidshttp://en.wikipedia.org/wiki/Blood_lipidshttp://en.wikipedia.org/wiki/Blood_lipidshttp://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-ErowidMSDS-27http://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-ErowidMSDS-27http://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-ErowidMSDS-27http://en.wikipedia.org/wiki/Journal_of_the_American_Chemical_Societyhttp://en.wikipedia.org/wiki/Journal_of_the_American_Chemical_Societyhttp://en.wikipedia.org/wiki/Journal_of_the_American_Chemical_Societyhttp://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-doi10.1021.2Fja01062a046-6http://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-doi10.1021.2Fja01062a046-6http://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-doi10.1021.2Fja01062a046-6http://en.wikipedia.org/wiki/Academic_journalhttp://en.wikipedia.org/wiki/Academic_journalhttp://en.wikipedia.org/wiki/Science_%28journal%29http://en.wikipedia.org/wiki/Science_%28journal%29http://en.wikipedia.org/wiki/Science_%28journal%29http://en.wikipedia.org/wiki/Raphael_Mechoulamhttp://en.wikipedia.org/wiki/Raphael_Mechoulamhttp://en.wikipedia.org/wiki/Raphael_Mechoulamhttp://en.wikipedia.org/wiki/Raphael_Mechoulamhttp://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-28http://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-28http://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-28http://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-29http://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-29http://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-29http://en.wikipedia.org/wiki/Hebrew_University_of_Jerusalemhttp://en.wikipedia.org/wiki/Hebrew_University_of_Jerusalemhttp://en.wikipedia.org/wiki/Hebrew_University_of_Jerusalemhttp://en.wikipedia.org/wiki/Tel_Aviv_Universityhttp://en.wikipedia.org/wiki/Tel_Aviv_Universityhttp://en.wikipedia.org/wiki/Tel_Aviv_Universityhttp://en.wikipedia.org/wiki/Hashishhttp://en.wikipedia.org/wiki/Hashishhttp://en.wikipedia.org/wiki/Hashishhttp://en.wikipedia.org/wiki/AIDShttp://en.wikipedia.org/wiki/AIDShttp://en.wikipedia.org/wiki/AIDShttp://en.wikipedia.org/wiki/Chemotherapyhttp://en.wikipedia.org/wiki/Chemotherapyhttp://en.wikipedia.org/wiki/Chemotherapyhttp://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-30http://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-30http://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-32http://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-32http://en.wikipedia.org/wiki/Glaucomahttp://en.wikipedia.org/wiki/Glaucomahttp://en.wikipedia.org/wiki/Glaucomahttp://en.wikipedia.org/wiki/Multiple_sclerosishttp://en.wikipedia.org/wiki/Multiple_sclerosishttp://en.wikipedia.org/wiki/Multiple_sclerosishttp://en.wikipedia.org/wiki/Neuropathic_painhttp://en.wikipedia.org/wiki/Neuropathic_painhttp://en.wikipedia.org/wiki/Neuropathic_painhttp://en.wikipedia.org/wiki/Neuropathic_painhttp://en.wikipedia.org/wiki/Spasticityhttp://en.wikipedia.org/wiki/Spasticityhttp://en.wikipedia.org/wiki/Spasticityhttp://en.wikipedia.org/wiki/National_Multiple_Sclerosis_Societyhttp://en.wikipedia.org/wiki/National_Multiple_Sclerosis_Societyhttp://en.wikipedia.org/wiki/National_Multiple_Sclerosis_Societyhttp://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-MS_society-34http://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-MS_society-34http://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-MS_society-34http://en.wikipedia.org/wiki/Clinical_study#Phase_IVhttp://en.wikipedia.org/wiki/Clinical_study#Phase_IVhttp://en.wikipedia.org/wiki/Clinical_study#Phase_IVhttp://en.wikipedia.org/wiki/Hadassah_Medical_Centerhttp://en.wikipedia.org/wiki/Hadassah_Medical_Centerhttp://en.wikipedia.org/wiki/Hadassah_Medical_Centerhttp://en.wikipedia.org/wiki/Post-traumatic_stress_disorderhttp://en.wikipedia.org/wiki/Post-traumatic_stress_disorderhttp://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-urlAdd_on_Study_on_.CE.949-THC_Treatment_for_Posttraumatic_Stress_Disorders_.28PTSD.29_-_Full_Text_View_-_ClinicalTrials.gov-35http://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-urlAdd_on_Study_on_.CE.949-THC_Treatment_for_Posttraumatic_Stress_Disorders_.28PTSD.29_-_Full_Text_View_-_ClinicalTrials.gov-35http://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-urlAdd_on_Study_on_.CE.949-THC_Treatment_for_Posttraumatic_Stress_Disorders_.28PTSD.29_-_Full_Text_View_-_ClinicalTrials.gov-35http://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-36http://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-36http://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-38http://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-38http://en.wikipedia.org/wiki/Cannabinoid_receptorhttp://en.wikipedia.org/wiki/Cannabinoid_receptorhttp://en.wikipedia.org/wiki/Cannabinoid_receptorhttp://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-39http://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-39http://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-39http://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-Petro_1981-40http://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-Petro_1981-40http://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-Petro_1981-40http://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-Clifford_1983-41http://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-Clifford_1983-41http://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-Clifford_1983-41http://en.wikipedia.org/wiki/File:Trichomes_on_a_Cannabis_Sativa_Flower.jpghttp://en.wikipedia.org/wiki/File:Trichomes_on_a_Cannabis_Sativa_Flower.jpghttp://en.wikipedia.org/wiki/File:Trichomes_on_a_Cannabis_Sativa_Flower.jpghttp://en.wikipedia.org/wiki/File:Trichomes_on_a_Cannabis_Sativa_Flower.jpghttp://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-Clifford_1983-41http://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-Petro_1981-40http://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-39http://en.wikipedia.org/wiki/Cannabinoid_receptorhttp://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-38http://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-36http://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-36http://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-urlAdd_on_Study_on_.CE.949-THC_Treatment_for_Posttraumatic_Stress_Disorders_.28PTSD.29_-_Full_Text_View_-_ClinicalTrials.gov-35http://en.wikipedia.org/wiki/Post-traumatic_stress_disorderhttp://en.wikipedia.org/wiki/Hadassah_Medical_Centerhttp://en.wikipedia.org/wiki/Clinical_study#Phase_IVhttp://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-MS_society-34http://en.wikipedia.org/wiki/National_Multiple_Sclerosis_Societyhttp://en.wikipedia.org/wiki/Spasticityhttp://en.wikipedia.org/wiki/Neuropathic_painhttp://en.wikipedia.org/wiki/Neuropathic_painhttp://en.wikipedia.org/wiki/Multiple_sclerosishttp://en.wikipedia.org/wiki/Glaucomahttp://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-32http://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-32http://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-30http://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-30http://en.wikipedia.org/wiki/Chemotherapyhttp://en.wikipedia.org/wiki/AIDShttp://en.wikipedia.org/wiki/Hashishhttp://en.wikipedia.org/wiki/Tel_Aviv_Universityhttp://en.wikipedia.org/wiki/Hebrew_University_of_Jerusalemhttp://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-29http://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-28http://en.wikipedia.org/wiki/Raphael_Mechoulamhttp://en.wikipedia.org/wiki/Raphael_Mechoulamhttp://en.wikipedia.org/wiki/Science_%28journal%29http://en.wikipedia.org/wiki/Academic_journalhttp://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-doi10.1021.2Fja01062a046-6http://en.wikipedia.org/wiki/Journal_of_the_American_Chemical_Societyhttp://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-ErowidMSDS-27http://en.wikipedia.org/wiki/Blood_lipidshttp://en.wikipedia.org/wiki/Toxicityhttp://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-26http://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-Walker_and_Huang-25


9/14

Several studies have been conducted with spinal injury patients and THC. Decreased tremor occurred

in 2/5 patients in a 1986 double-blind, placebo-controlled crossover study.[42]

THC was shown to

decrease spasticity and pain in a 1990 double-blind, placebo-controlled study.[43]

Studies in animals and in vitro

There is evidence to suggest THC can preventAlzheimer's Diseasein ananimal modelby preventingthe inflammation caused bymicrogliacells which are activated by binding ofamyloidprotein.

[44]

In 2006, researchers fromScripps Research Institute, using bothcomputer modelingandbiochemical

assays, found THC "may provide an improved therapeutic forAlzheimer's disease" that would treat

"both the symptoms and progression" of the disease. THC, they found, inhibits the formation of

amyloid plaque(the primary marker for Alzheimer's disease). The authors concluded that their

research offered "convincing evidence that THC possesses remarkable inhibitory qualities."[45]

THC

was found to be "considerably more effective" than two of the leading Alzheimer's drugs on the

market,donepezilandtacrine.[46]

THC may also be an effective cancer treatment, with studies showing tumor size reduction in miceconducted in 1975[47]

and 2007,[48]

as well as in a pilot study in humans withglioblastoma multiforme

(a type of brain cancer).[49]

THC has also been found to attenuate conditioned retching and sickness,

experimentally verifying anecdotal reports that THC alleviates nausea and vomiting when undergoing

chemotherapy.[50]

A two-year study in which rats and mice were force-fed tetrahydrocannabinol dissolved in corn oil

showed reduced body mass, enhanced survival rates, and decreased tumor incidences in several

sites, mainly organs under hormonal control. It also causedtesticular atrophyand uterine and

ovarianhypoplasia, as well as hyperactivity and convulsions immediately after administration, of

which the onset and frequency were dose related.[51]

Research in rats indicates that THC preventshydroperoxide-inducedoxidative damageas well as orbetter than otherantioxidantsin a chemical (Fenton reaction) system andneuronalcultures.

[52]In

micelow doses of 9-THC reduces the progression ofatherosclerosis.[53]

Research has also shown that past claims of brain damage from cannabis use fail to hold up to the

scientific method.[54]

Instead, recent studies with synthetic cannabinoids show that activation of CB1

receptors can facilitateneurogenesis,[55]

as well as neuroprotection,[56]

and can even help prevent

natural neural degradation from neurodegenerative diseases such as MS, Parkinson's, and

Alzheimer's. This, along with research into the CB2 receptor (throughout the immune system), has

given the case for medical marijuana more support.[57][58]

THC is both a CB1 and CB2 agonist.[59]

Scientific studies indicating side-effects

Conceivable long-term ill effects of THC on humans are disputed but not improbable, yet its status as

an illegal drug in most countries can make research difficult, for instance in the United States where

theNational Institute on Drug Abusewas the only legal source of cannabis for researchers until it

recently became legalized in Colorado and Washington.[60]

Some studies claim a variety of negative effects associated with long-term use, including short-term

memory loss.[61][62]

Usingpositron emission tomography(PET), one study reports altered memory-

related brain function (23% better memory for the cannabis users in recalling the end of a list of

things to remember, but 19% worse memory for cannabis users in recalling the middle of a list of

things to remember) in chronic daily cannabis users.[63]
http://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-Hanigan_1986-42http://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-Hanigan_1986-42http://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-Hanigan_1986-42http://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-Maurer_1990-43http://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-Maurer_1990-43http://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-Maurer_1990-43http://en.wikipedia.org/wiki/Alzheimer%27s_Diseasehttp://en.wikipedia.org/wiki/Alzheimer%27s_Diseasehttp://en.wikipedia.org/wiki/Alzheimer%27s_Diseasehttp://en.wikipedia.org/wiki/Animal_modelhttp://en.wikipedia.org/wiki/Animal_modelhttp://en.wikipedia.org/wiki/Animal_modelhttp://en.wikipedia.org/wiki/Microgliahttp://en.wikipedia.org/wiki/Microgliahttp://en.wikipedia.org/wiki/Microgliahttp://en.wikipedia.org/wiki/Amyloidhttp://en.wikipedia.org/wiki/Amyloidhttp://en.wikipedia.org/wiki/Amyloidhttp://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-pmid15728830-44http://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-pmid15728830-44http://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-pmid15728830-44http://en.wikipedia.org/wiki/Scripps_Research_Institutehttp://en.wikipedia.org/wiki/Scripps_Research_Institutehttp://en.wikipedia.org/wiki/Scripps_Research_Institutehttp://en.wikipedia.org/wiki/Computer_modelinghttp://en.wikipedia.org/wiki/Computer_modelinghttp://en.wikipedia.org/wiki/Computer_modelinghttp://en.wikipedia.org/wiki/Biochemical_assayshttp://en.wikipedia.org/wiki/Biochemical_assayshttp://en.wikipedia.org/wiki/Biochemical_assayshttp://en.wikipedia.org/wiki/Biochemical_assayshttp://en.wikipedia.org/wiki/Alzheimer%27s_diseasehttp://en.wikipedia.org/wiki/Alzheimer%27s_diseasehttp://en.wikipedia.org/wiki/Alzheimer%27s_diseasehttp://en.wikipedia.org/wiki/Amyloid_plaque#Amyloid_pathologyhttp://en.wikipedia.org/wiki/Amyloid_plaque#Amyloid_pathologyhttp://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-45http://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-45http://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-45http://en.wikipedia.org/wiki/Donepezilhttp://en.wikipedia.org/wiki/Donepezilhttp://en.wikipedia.org/wiki/Donepezilhttp://en.wikipedia.org/wiki/Tacrinehttp://en.wikipedia.org/wiki/Tacrinehttp://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-46http://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-46http://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-46http://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-47http://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-47http://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-47http://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-48http://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-48http://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-48http://en.wikipedia.org/wiki/Glioblastoma_multiformehttp://en.wikipedia.org/wiki/Glioblastoma_multiformehttp://en.wikipedia.org/wiki/Glioblastoma_multiformehttp://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-49http://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-49http://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-49http://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-Kemp-50http://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-Kemp-50http://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-Kemp-50http://en.wikipedia.org/wiki/Testicular_atrophyhttp://en.wikipedia.org/wiki/Testicular_atrophyhttp://en.wikipedia.org/wiki/Testicular_atrophyhttp://en.wikipedia.org/wiki/Hypoplasiahttp://en.wikipedia.org/wiki/Hypoplasiahttp://en.wikipedia.org/wiki/Hypoplasiahttp://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-51http://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-51http://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-51http://en.wikipedia.org/wiki/Hydroperoxidehttp://en.wikipedia.org/wiki/Hydroperoxidehttp://en.wikipedia.org/wiki/Hydroperoxidehttp://en.wikipedia.org/wiki/Oxidative_damagehttp://en.wikipedia.org/wiki/Oxidative_damagehttp://en.wikipedia.org/wiki/Oxidative_damagehttp://en.wikipedia.org/wiki/Antioxidanthttp://en.wikipedia.org/wiki/Antioxidanthttp://en.wikipedia.org/wiki/Antioxidanthttp://en.wikipedia.org/wiki/Fenton_reactionhttp://en.wikipedia.org/wiki/Fenton_reactionhttp://en.wikipedia.org/wiki/Fenton_reactionhttp://en.wikipedia.org/wiki/Neuronhttp://en.wikipedia.org/wiki/Neuronhttp://en.wikipedia.org/wiki/Neuronhttp://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-pmid9653176-52http://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-pmid9653176-52http://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-pmid9653176-52http://en.wikipedia.org/wiki/Micehttp://en.wikipedia.org/wiki/Micehttp://en.wikipedia.org/wiki/Atherosclerosishttp://en.wikipedia.org/wiki/Atherosclerosishttp://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-pmid15815632-53http://en.wikipedia.org/wiki/Tetrahydrocannabinol#cite_note-pmid15815632-53http://en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Some studies have suggested that cannabis users have a greater risk of developingpsychosisthan

non-users. This risk is most pronounced in cases with an existing risk of psychotic disorder.[64]

Other

studies have made similar associations, especially in individuals predisposed to psychosis prior to

cannabis use.[65]

A 2005 paper from theDunedin studysuggested an increased risk in the

development of psychosis linked to polymorphisms in the COMT gene.[66]

However, a more recent

study cast doubt on the proposed connection between this gene and the effects of cannabis on thedevelopment of psychosis.

[67]

A 2008 German review reported that cannabis was a causal factor in some cases of schizophrenia

and stressed the need for better education among the public due to increasingly relaxed access to

cannabis.[68]

Though cannabis use has increased dramatically in several countries over the past few

decades, the rates of psychosis and schizophrenia have not generally increased, casting some doubt

over whether the drug can cause cases that would not otherwise have occurred.[69]

Conversely, research from 2007 reported a correlation between cannabis use and increasedcognitive

function in schizophrenic patients.[70]

A 2008National Institutes of Healthstudy of 19 chronic heavy marijuana users with cardiac andcerebral abnormalities (averaging 28g to 272g (1 to 9+ oz) weekly) and 24 controls found elevated

levels ofapolipoprotein C-III(apoC-III) in the chronic smokers.[71]

An increase in apoC-III levels

induces the development ofhypertriglyceridemia.

A 2008 study by theUniversity of Melbourneof 15 heavy marijuana users (consuming at least 5

marijuana cigarettes daily for on average 20 years) and 16 controls found an average size difference

for the smokers in thehippocampus(12 percent smaller) and theamygdala(7 percent smaller).[72]

It

has been suggested that such effects can be reversed with long term abstinence.[73]

A 2008 study atKarolinska Institutesuggested that young rats treated withTHCreceived an

increased motivation for drug use, heroin in the study, under conditions of stress.[74][75]

A study of around 1000 people in New Zealand found that starting cannabis below the age of 18,

when the brain is undergoing major development, induces a 8 point IQ drop on average. This effect

was not fully reverted after stopping cannabis use. However, starting cannabis older seems to be

safer.[76]

Opinions and statistical observations indicating side-effects

A literature review on the subject concluded that "Cannabis use appears to be neither a sufficient nor

a necessary cause for psychosis. It is a component cause, part of a complex constellation of factors

leading to psychosis."[77]

In other words, THC and other active substances of cannabis may

accentuate symptoms in people already predisposed, but likely don't cause psychotic disorders on

their own. However, a French review from 2009 came to a conclusion that cannabis use, particularly

that before age 15, was a factor in the development of schizophrenic disorders.[78]

A 2009 study found that there was a high prevalence of cannabis in the toxicological analysis of

homicide (22%) and suicide victims (11%) in Australia.[79]

In a similar study from Sweden it was also

found that suicide victims had a significantly higher use of cannabis, but the authors found that "this

was explained by markers of psychological and behavioral problems."[80]

Biosynthesis
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