11-nor-9-Carboxy-THC
Encyclopedia
11-nor-9-Carboxy-THC, also known as 11-nor-9-carboxy-delta-9-tetrahydrocannabinol, 11-COOH-THC, THC-COOH, and THC-11-oic acid, is the main secondary metabolite
of THC
which is formed in the body after Cannabis
is consumed.
11-COOH-THC is formed in the body by oxidation of the active metabolite 11-Hydroxy-THC
by liver enzymes. It is then metabolized further by conjugation with glucuronide
, forming a water-soluble congener which can be more easily excreted by the body.
11-COOH-THC is not psychoactive itself, but has a long half-life in the body of up to several days (or even weeks in very heavy users), making it the main metabolite tested for when blood or urine testing
for cannabis use. More sensitive tests are able to distinguish between 11-OH-THC and 11-COOH-THC, which can help determine how recently cannabis was consumed; if only 11-COOH-THC is present then the cannabis was used some time ago and any impairment in cognitive ability or motor function will have dissipated, whereas if both 11-OH-THC and 11-COOH-THC are present then the cannabis was consumed more recently and motor impairment may still be present.
Some jurisdictions where cannabis use is decriminalized or permitted under some circumstances use such tests when determining whether drivers were legally intoxicated
and therefore unfit to drive, with the comparative levels of THC, 11-OH-THC and 11-COOH-THC being used to derive a "blood cannabis level" analogous to the blood alcohol level used in prosecuting impaired drivers. On the other hand in jurisdictions where cannabis is completely illegal, any detectable levels of 11-COOH-THC may be deemed to constitute driving while intoxicated, even though this approach has been criticized as tantamount to prohibition of "driving whilst being a regular user of cannabis" regardless of the presence or absence of any actual impairment that might impact on driving performance.
While 11-COOH-THC does not have any psychoactive effects in its own right, it may still have a role in the analgesic
and antiinflammatory effects of cannabis, and has also been shown to moderate the effects of THC itself which may help explain the difference in subjective effects seen between occasional and regular users of cannabis.
Metabolite
Metabolites are the intermediates and products of metabolism. The term metabolite is usually restricted to small molecules. A primary metabolite is directly involved in normal growth, development, and reproduction. Alcohol is an example of a primary metabolite produced in large-scale by industrial...
of THC
Tetrahydrocannabinol
Tetrahydrocannabinol , also known as delta-9-tetrahydrocannabinol , Δ1-THC , or dronabinol, is the main chemical psychoactive substance found in the cannabis plant. It was first isolated in 1964. In pure form, it is a glassy solid when cold, and becomes viscous and sticky if warmed...
which is formed in the body after Cannabis
Cannabis
Cannabis is a genus of flowering plants that includes three putative species, Cannabis sativa, Cannabis indica, and Cannabis ruderalis. These three taxa are indigenous to Central Asia, and South Asia. Cannabis has long been used for fibre , for seed and seed oils, for medicinal purposes, and as a...
is consumed.
11-COOH-THC is formed in the body by oxidation of the active metabolite 11-Hydroxy-THC
11-Hydroxy-THC
11-Hydroxy-Δ9-tetrahydrocannabinol, abbreviated as 11-OH-THC, is the main active metabolite of THC which is formed in the body after cannabis consumption. 11-Hydroxy-THC has been shown to be active in its own right, but the effects produced are not necessarily identical to those of THC...
by liver enzymes. It is then metabolized further by conjugation with glucuronide
Glucuronide
A glucuronide, also known as glucuronoside, is any substance produced by linking glucuronic acid to another substance via a glycosidic bond...
, forming a water-soluble congener which can be more easily excreted by the body.
11-COOH-THC is not psychoactive itself, but has a long half-life in the body of up to several days (or even weeks in very heavy users), making it the main metabolite tested for when blood or urine testing
Drug test
A drug test is a technical analysis of a biological specimen – for example urine, hair, blood, sweat, or oral fluid / saliva – to determine the presence or absence of specified parent drugs or their metabolites...
for cannabis use. More sensitive tests are able to distinguish between 11-OH-THC and 11-COOH-THC, which can help determine how recently cannabis was consumed; if only 11-COOH-THC is present then the cannabis was used some time ago and any impairment in cognitive ability or motor function will have dissipated, whereas if both 11-OH-THC and 11-COOH-THC are present then the cannabis was consumed more recently and motor impairment may still be present.
Some jurisdictions where cannabis use is decriminalized or permitted under some circumstances use such tests when determining whether drivers were legally intoxicated
Driving under the influence
Driving under the influence is the act of driving a motor vehicle with blood levels of alcohol in excess of a legal limit...
and therefore unfit to drive, with the comparative levels of THC, 11-OH-THC and 11-COOH-THC being used to derive a "blood cannabis level" analogous to the blood alcohol level used in prosecuting impaired drivers. On the other hand in jurisdictions where cannabis is completely illegal, any detectable levels of 11-COOH-THC may be deemed to constitute driving while intoxicated, even though this approach has been criticized as tantamount to prohibition of "driving whilst being a regular user of cannabis" regardless of the presence or absence of any actual impairment that might impact on driving performance.
While 11-COOH-THC does not have any psychoactive effects in its own right, it may still have a role in the analgesic
Analgesic
An analgesic is any member of the group of drugs used to relieve pain . The word analgesic derives from Greek an- and algos ....
and antiinflammatory effects of cannabis, and has also been shown to moderate the effects of THC itself which may help explain the difference in subjective effects seen between occasional and regular users of cannabis.