11-Nor-9-carboxy-THC

Main secondary metabolite of THC April 2024 vanc Tetrahydrocannabinolic acid changed 477189426 1-Hydroxy-6,6-dimethyl-3-pentyl-6a,7,8,10a-tetrahydrobenzo[c]chromene-9-carboxylic acid 11-COOH-THC.svg skin-invert-image 250px THC-11-oic-acid-3D-balls.png bg-transparent THC-11-oic acid molecule Inconclusive Variable Variable Variable 5.2 to 6.2 days Schwilke EW, Schwope DM, Karschner EL, Lowe RH, Darwin WD, Kelly DL, Goodwin RS, Gorelick DA, Huestis MA 6 Delta9-tetrahydrocannabinol (THC), 11-hydroxy-THC, and 11-nor-9-carboxy-THC plasma pharmacokinetics during and after continuous high-dose oral THC Clinical Chemistry 55 12 2180–2189 December 2009 19833841 3196989 10.1373/clinchem.2008.122119 Variable changed ?? 56354-06-4 correct FDA 4TPC9E4A32 107885 correct drugbank correct chemspider 97019 167808 21 28 4 CCCCCc1cc(c2c(c1)OC(C3C2C=C(CC3)C(=O)O)(C)C)O correct chemspider 1S/C21H28O4/c1-4-5-6-7-13-10-17(22)19-15-12-14(20(23)24)8-9-16(15)21(2,3)25-18(19)11-13/h10-12,15-16,22H,4-9H2,1-3H3,(H,23,24) correct chemspider YOVRGSHRZRJTLZ-UHFFFAOYSA-N 11-Nor-9-carboxy-Δ9-tetrahydrocannabinol (11-COOH-THC or THC-COOH), often referred to as 11-nor-9-carboxy-THC or THC-11-oic acid, is the main secondary metabolite of tetrahydrocannabinol (THC) which is formed in the body after cannabis is consumed. Metabolism and detection 11-COOH-THC is formed in the body by oxidation of the active metabolite 11-hydroxy-THC (11-OH-THC) by liver enzymes. It is then metabolized further by conjugation with glucuronide, Skopp G, Pötsch L Stability of 11-nor-delta(9)-carboxy-tetrahydrocannabinol glucuronide in plasma and urine assessed by liquid chromatography-tandem mass spectrometry Clinical Chemistry 48 2 301–306 February 2002 11805011 10.1093/clinchem/48.2.301 free forming a water-soluble congener which can be more easily excreted by the body. Law B, Mason PA, Moffat AC, King LJ 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 1984 6323852 10.1093/jat/8.1.19 11-COOH-THC has a long half-life in the body of up to several days (or even weeks in very heavy users), Huestis MA, Mitchell JM, Cone EJ Detection times of marijuana metabolites in urine by immunoassay and GC-MS Journal of Analytical Toxicology 19 6 443–449 October 1995 8926739 10.1093/jat/19.6.443 Pope HG, Gruber AJ, Hudson JI, Huestis MA, Yurgelun-Todd D Neuropsychological performance in long-term cannabis users Archives of General Psychiatry 58 10 909–915 October 2001 11576028 10.1001/archpsyc.58.10.909 free Dietz L, Glaz-Sandberg A, Nguyen H, Skopp G, Mikus G, Aderjan R The urinary disposition of intravenously administered 11-nor-9-carboxy-delta-9-tetrahydrocannabinol in humans Therapeutic Drug Monitoring 29 3 368–372 June 2007 17529896 10.1097/FTD.0b013e31805ba6fd 25321236 making it the main metabolite tested for 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; Huestis MA, Henningfield JE, Cone EJ 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 5 283–290 1992 1338216 10.1093/jat/16.5.283 Huestis MA, Elsohly M, Nebro W, Barnes A, Gustafson RA, Smith ML Estimating time of last oral ingestion of cannabis from plasma THC and THCCOOH concentrations Therapeutic Drug Monitoring 28 4 540–544 August 2006 16885722 10.1097/00007691-200608000-00009 22536528 if only 11-COOH-THC is present then 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 cannabis was consumed more recently and motor impairment may still be present.2025-03-21 11-Nor-9-carboxy-THC Metabolism and Detectio https://purplebreak.com/blogs/blog/11-nor-9-carboxy-thc-metabolism-detection 2025-03-21 PurpleBreak en Recent studies highlight that individual factors such as metabolism, body fat percentage, and frequency of use significantly impact the detection window of 11-COOH-THC in drug testing. 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. Ménétrey A, Augsburger M, Favrat B, Pin MA, Rothuizen LE, Appenzeller M, Buclin T, Mangin P, Giroud C 6 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 5 327–338 2005 16105257 10.1093/jat/29.5.327 free 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 driving performance. Effects While 11-COOH-THC does not have any psychoactive effects in its own right, it may still have a role in the analgesic and anti-inflammatory effects of cannabis, Burstein SH, Hull K, Hunter SA, Latham V Cannabinoids and pain responses: a possible role for prostaglandins FASEB Journal 2 14 3022–3026 November 1988 2846397 10.1096/fasebj.2.14.2846397 free 46552755 Doyle SA, Burstein SH, Dewey WL, Welch SP Further studies on the antinociceptive effects of delta 6-THC-7-oic acid Agents and Actions 31 1–2 157–163 August 1990 2178317 10.1007/bf02003237 23310488 Ujváry I, Grotenhermen F 11-Nor-9-carboxy-Δ9-tetrahydrocannabinol – a ubiquitous yet underresearched cannabinoid. A review of the literature Cannabinoids 9 1 1–8 2014 http://www.cannabis-med.org/data/pdf/en_2014_01_1.pdf 2014-06-25 2017-04-20 https://web.archive.org/web/20170420192452/http://www.cannabis-med.org/data/pdf/en_2014_01_1.pdf dead 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. Burstein S, Hunter SA, Latham V, Renzulli L A major metabolite of delta 1-tetrahydrocannabinol reduces its cataleptic effect in mice Experientia 43 4 402–403 April 1987 3032669 10.1007/BF01940427 22153383 Burstein S, Hunter SA, Latham V, Renzulli L Prostaglandins and cannabis--XVI. Antagonism of delta 1-tetrahydrocannabinol action by its metabolites Biochemical Pharmacology 35 15 2553–2558 August 1986 3017356 10.1016/0006-2952(86)90053-5 Legal status The legal status of 11-nor-9-carboxy-THC varies among jurisdictions. Australia 11-COOH-THC is a Schedule 8 prohibited substance in Western Australia under the Poisons Standard (July 2016).Poisons Standard July 2016 Comlaw.gov.au A schedule 8 substance is a controlled Drug – Substances which should be available for use but require restriction of manufacture, supply, distribution, possession and use to reduce abuse, misuse and physical or psychological dependence. United States Because 11-COOH-THC is substantially similar to the Schedule I controlled substance THC, possession or sale of 11-COOH-THC could be subject to prosecution under the Federal Analog Act. See also Lenabasum Cannabis drug testing References Category:Cannabinoids Category:Carboxylic acids Category:Benzochromenes Category:Hydroxyarenes Category:Prodrugs Category:Recreational drug metabolites Category:Heterocyclic compounds with 3 rings