11-nor-9-Carboxy-THC

Not to be confused with Tetrahydrocannabinolic acid.
11-nor-9-Carboxy-THC
THC-11-oic acid molecule
Systematic (IUPAC) name
1-hydroxy-6,6-dimethyl-3-pentyl-6a,7,8,10a-tetrahydrobenzo[c]chromene-9-carboxylic acid
Clinical data
Pregnancy
category
  • Inconclusive
Routes of
administration		 Variable
Legal status
  • Variable
Pharmacokinetic data
Bioavailability Variable
Metabolism Variable
Biological half-life 5.2 to 6.2 days [1]
Excretion Variable
Identifiers
CAS Number 64280-14-4 N
PubChem CID 107885
ChemSpider 97019 YesY
Chemical data
Formula C21H28O4
Molar mass 344.445 g/mol
 NYesY (what is this?)  (verify)

11-nor-9-Carboxy-THC, also known as 11-nor-9-carboxy-delta-9-tetrahydrocannabinol, 11-nor-9-carboxy-delta-9-THC, 11-COOH-THC, THC-COOH, and THC-11-oic acid, is the main secondary metabolite of tetrahydrocannabinol (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 (also known as 11-OH-THC) by liver enzymes. It is then metabolized further by conjugation with glucuronide,[2] forming a water-soluble congener which can be more easily excreted by the body.[3]

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),[4][5][6] making it the main metabolite tested for when blood or urine testing for cannabis use. More selective tests are able to distinguish between 11-OH-THC and 11-COOH-THC, which can help determine how recently cannabis was consumed;[7][8] 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.[9] 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 recent 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,[10][11][12] 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.[13][14]

References

  1. ↑ http://www.clinchem.org/cgi/content/full/55/12/2180
  2. ↑ Skopp, G; Pötsch, L (2002). "Stability of 11-nor-delta(9)-carboxy-tetrahydrocannabinol glucuronide in plasma and urine assessed by liquid chromatography-tandem mass spectrometry". Clinical Chemistry 48 (2): 301–6. PMID 11805011.
  3. ↑ Law, B; Mason, PA; Moffat, AC; King, LJ (1984). "Confirmation of cannabis use by the analysis of delta 9-tetrahydrocannabinol metabolites in blood and urine by combined HPLC and RIA". Journal of analytical toxicology 8 (1): 19–22. doi:10.1093/jat/8.1.19. PMID 6323852.
  4. ↑ Huestis, MA; Mitchell, JM; Cone, EJ (1995). "Detection times of marijuana metabolites in urine by immunoassay and GC-MS". Journal of analytical toxicology 19 (6): 443–9. doi:10.1093/jat/19.6.443. PMID 8926739.
  5. ↑ Pope Jr, HG; Gruber, AJ; Hudson, JI; Huestis, MA; Yurgelun-Todd, D (2001). "Neuropsychological performance in long-term cannabis users". Archives of General Psychiatry 58 (10): 909–15. doi:10.1001/archpsyc.58.10.909. PMID 11576028.
  6. ↑ Dietz, L; Glaz-Sandberg, A; Nguyen, H; Skopp, G; Mikus, G; Aderjan, R (2007). "The urinary disposition of intravenously administered 11-nor-9-carboxy-delta-9-tetrahydrocannabinol in humans". Therapeutic drug monitoring 29 (3): 368–72. doi:10.1097/FTD.0b013e31805ba6fd. PMID 17529896.
  7. ↑ Huestis, MA; Henningfield, JE; Cone, EJ (1992). "Blood cannabinoids. II. Models for the prediction of time of marijuana exposure from plasma concentrations of delta 9-tetrahydrocannabinol (THC) and 11-nor-9-carboxy-delta 9-tetrahydrocannabinol (THCCOOH)". Journal of analytical toxicology 16 (5): 283–90. doi:10.1093/jat/16.5.283. PMID 1338216.
  8. ↑ Huestis, MA; Elsohly, M; Nebro, W; Barnes, A; Gustafson, RA; Smith, ML (2006). "Estimating time of last oral ingestion of cannabis from plasma THC and THCCOOH concentrations". Therapeutic drug monitoring 28 (4): 540–4. doi:10.1097/00007691-200608000-00009. PMID 16885722.
  9. ↑ Ménétrey, A; Augsburger, M; Favrat, B; Pin, MA; Rothuizen, LE; Appenzeller, M; Buclin, T; Mangin, P; Giroud, C (2005). "Assessment of driving capability through the use of clinical and psychomotor tests in relation to blood cannabinoids levels following oral administration of 20 mg dronabinol or of a cannabis decoction made with 20 or 60 mg Delta9-THC". Journal of analytical toxicology 29 (5): 327–38. doi:10.1093/jat/29.5.327. PMID 16105257.
  10. ↑ Burstein, SH; Hull, K; Hunter, SA; Latham, V (1988). "Cannabinoids and pain responses: a possible role for prostaglandins". The FASEB Journal 2 (14): 3022–6. PMID 2846397.
  11. ↑ Doyle, SA; Burstein, SH; Dewey, WL; Welch, SP (1990). "Further studies on the antinociceptive effects of delta 6-THC-7-oic acid". Agents and actions 31 (1–2): 157–63. doi:10.1007/bf02003237. PMID 2178317.
  12. ↑ Ujváry, I; Grotenhermen, F (2014). "11-Nor-9-carboxy-Δ9-tetrahydrocannabinol – a ubiquitous yet underresearched cannabinoid. A review of the literature" (PDF). Cannabinoids 9 (1): 1–8.
  13. ↑ Burstein, S; Hunter, SA; Latham, V; Renzulli, L (1987). "A major metabolite of delta 1-tetrahydrocannabinol reduces its cataleptic effect in mice". Experientia 43 (4): 402–3. doi:10.1007/BF01940427. PMID 3032669.
  14. ↑ Burstein, S; Hunter, SA; Latham, V; Renzulli, L (1986). "Prostaglandins and cannabis--XVI. Antagonism of delta 1-tetrahydrocannabinol action by its metabolites". Biochemical pharmacology 35 (15): 2553–8. doi:10.1016/0006-2952(86)90053-5. PMID 3017356.
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