| Revision as of 14:37, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{drugbox}} taken from revid 476482201 of page 11-nor-9-Carboxy-THC for the Chem/Drugbox validation project (updated: 'CAS_number'). |
Latest revision as of 18:03, 21 October 2024 edit JWBE (talk | contribs)Extended confirmed users10,126 edits removed Category:Phenols; added Category:Hydroxyarenes using HotCat |
| Line 1: |
Line 1: |
|
|
{{short description|Main secondary metabolite of THC}} |
|
{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid of page ] with values updated to verified values.}} |
|
|
|
{{MCN|date=April 2024}} |
|
|
{{cs1 config|name-list-style=vanc}} |
|
|
{{Distinguish|Tetrahydrocannabinolic acid}} |
|
{{Drugbox |
|
{{Drugbox |
|
|
| Verifiedfields = changed |
|
| verifiedrevid = 446003364 |
|
| verifiedrevid = 477189426 |
|
| IUPAC_name = 1-hydroxy-6,6-dimethyl-3-pentyl-6a,7,8,10a-tetrahydrobenzochromene-9-carboxylic acid |
|
| IUPAC_name = 1-Hydroxy-6,6-dimethyl-3-pentyl-6a,7,8,10a-tetrahydrobenzochromene-9-carboxylic acid |
|
| image = 11-COOH-THC.svg |
|
| image = 11-COOH-THC.svg |
|
| width = 250px |
|
| width = 250px |
|
|
| image2 = THC-11-oic-acid-3D-balls.png |
|
|
| alt2 = THC-11-oic acid molecule |
|
|
|
|
|
<!--Clinical data--> |
|
<!--Clinical data--> |
|
| tradename = |
|
| tradename = |
|
| pregnancy_category = Inconclusive |
|
| pregnancy_category = Inconclusive |
|
| legal_status = Variable |
|
| legal_status = |
|
| routes_of_administration = Variable |
|
| routes_of_administration = Variable |
|
|
|
|
| Line 15: |
Line 21: |
|
| bioavailability = Variable |
|
| bioavailability = Variable |
|
| metabolism = Variable |
|
| metabolism = Variable |
|
|
| elimination_half-life = 5.2 to 6.2 days <ref>{{cite journal | vauthors = Schwilke EW, Schwope DM, Karschner EL, Lowe RH, Darwin WD, Kelly DL, Goodwin RS, Gorelick DA, Huestis MA | display-authors = 6 | title = Delta9-tetrahydrocannabinol (THC), 11-hydroxy-THC, and 11-nor-9-carboxy-THC plasma pharmacokinetics during and after continuous high-dose oral THC | journal = Clinical Chemistry | volume = 55 | issue = 12 | pages = 2180–2189 | date = December 2009 | pmid = 19833841 | pmc = 3196989 | doi = 10.1373/clinchem.2008.122119 }}</ref> |
|
| elimination_half-life = 5.2 to 6.2 days <ref>http://www.clinchem.org/cgi/content/full/55/12/2180</ref> |
|
|
| excretion = Variable |
|
| excretion = Variable |
|
|
|
|
|
<!--Identifiers--> |
|
<!--Identifiers--> |
|
| CAS_number_Ref = {{cascite|correct|??}} |
|
| CAS_number_Ref = {{cascite|changed|??}} |
|
| CAS_number = <!-- blanked - oldvalue: 64280-14-4 --> |
|
| CAS_number = 56354-06-4 |
|
|
| UNII_Ref = {{fdacite|correct|FDA}} |
|
|
| UNII = 4TPC9E4A32 |
|
| PubChem = 107885 |
|
| PubChem = 107885 |
|
| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
|
| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
|
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
|
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
|
| ChemSpiderID = 97019 |
|
| ChemSpiderID = 97019 |
|
|
| ChEBI = 167808 |
|
|
|
|
|
<!--Chemical data--> |
|
<!--Chemical data--> |
|
| C=21 | H=28 | O=4 |
|
| C=21 | H=28 | O=4 |
|
| molecular_weight = 344.445 g/mol |
|
|
| smiles = CCCCCc1cc(c2c(c1)OC(C3C2C=C(CC3)C(=O)O)(C)C)O |
|
| smiles = CCCCCc1cc(c2c(c1)OC(C3C2C=C(CC3)C(=O)O)(C)C)O |
|
| InChI = 1/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) |
|
|
| InChIKey = YOVRGSHRZRJTLZ-UHFFFAOYAD |
|
|
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
|
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
|
| StdInChI = 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) |
|
| StdInChI = 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) |
|
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
|
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
|
| StdInChIKey = YOVRGSHRZRJTLZ-UHFFFAOYSA-N |
|
| StdInChIKey = YOVRGSHRZRJTLZ-UHFFFAOYSA-N |
|
|
|drug_name=|alt=|caption=|type=|MedlinePlus=|licence_EU=|pregnancy_AU=|pregnancy_US=|licence_US=|DrugBank=}} |
|
}} |
|
|
|
|
|
|
'''11-Nor-9-carboxy-Δ<sup>9</sup>-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 ] of ] (THC) which is formed in the body after ] is consumed. |
|
|
|
|
|
==Metabolism and detection== |
|
|
11-COOH-THC is formed in the body by ] of the active metabolite ] (11-OH-THC) by liver enzymes. It is then metabolized further by conjugation with ],<ref>{{cite journal | vauthors = Skopp G, Pötsch L | title = Stability of 11-nor-delta(9)-carboxy-tetrahydrocannabinol glucuronide in plasma and urine assessed by liquid chromatography-tandem mass spectrometry | journal = Clinical Chemistry | volume = 48 | issue = 2 | pages = 301–306 | date = February 2002 | pmid = 11805011 | doi = 10.1093/clinchem/48.2.301 | doi-access = free }}</ref> forming a water-soluble congener which can be more easily excreted by the body.<ref>{{cite journal | vauthors = Law B, Mason PA, Moffat AC, King LJ | title = Confirmation of cannabis use by the analysis of delta 9-tetrahydrocannabinol metabolites in blood and urine by combined HPLC and RIA | journal = Journal of Analytical Toxicology | volume = 8 | issue = 1 | pages = 19–22 | year = 1984 | pmid = 6323852 | doi = 10.1093/jat/8.1.19 }}</ref> |
|
|
|
|
|
11-COOH-THC has a long half-life in the body of up to several days (or even weeks in very heavy users),<ref>{{cite journal | vauthors = Huestis MA, Mitchell JM, Cone EJ | title = Detection times of marijuana metabolites in urine by immunoassay and GC-MS | journal = Journal of Analytical Toxicology | volume = 19 | issue = 6 | pages = 443–449 | date = October 1995 | pmid = 8926739 | doi = 10.1093/jat/19.6.443 }}</ref><ref>{{cite journal | vauthors = Pope HG, Gruber AJ, Hudson JI, Huestis MA, Yurgelun-Todd D | title = Neuropsychological performance in long-term cannabis users | journal = Archives of General Psychiatry | volume = 58 | issue = 10 | pages = 909–915 | date = October 2001 | pmid = 11576028 | doi = 10.1001/archpsyc.58.10.909 | doi-access = free }}</ref><ref>{{cite journal | vauthors = Dietz L, Glaz-Sandberg A, Nguyen H, Skopp G, Mikus G, Aderjan R | title = The urinary disposition of intravenously administered 11-nor-9-carboxy-delta-9-tetrahydrocannabinol in humans | journal = Therapeutic Drug Monitoring | volume = 29 | issue = 3 | pages = 368–372 | date = June 2007 | pmid = 17529896 | doi = 10.1097/FTD.0b013e31805ba6fd | s2cid = 25321236 }}</ref> making it the main metabolite tested for ] 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;<ref>{{cite journal | vauthors = Huestis MA, Henningfield JE, Cone EJ | title = 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 = Journal of Analytical Toxicology | volume = 16 | issue = 5 | pages = 283–290 | year = 1992 | pmid = 1338216 | doi = 10.1093/jat/16.5.283 }}</ref><ref>{{cite journal | vauthors = Huestis MA, Elsohly M, Nebro W, Barnes A, Gustafson RA, Smith ML | title = Estimating time of last oral ingestion of cannabis from plasma THC and THCCOOH concentrations | journal = Therapeutic Drug Monitoring | volume = 28 | issue = 4 | pages = 540–544 | date = August 2006 | pmid = 16885722 | doi = 10.1097/00007691-200608000-00009 | s2cid = 22536528 }}</ref> 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.{{Citation needed|date=March 2017}} |
|
|
|
|
|
Some jurisdictions where cannabis use is decriminalized or permitted under some circumstances use such tests when determining whether drivers were ] 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.<ref>{{cite journal | vauthors = Ménétrey A, Augsburger M, Favrat B, Pin MA, Rothuizen LE, Appenzeller M, Buclin T, Mangin P, Giroud C | display-authors = 6 | title = 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 = Journal of Analytical Toxicology | volume = 29 | issue = 5 | pages = 327–338 | year = 2005 | pmid = 16105257 | doi = 10.1093/jat/29.5.327 | doi-access = free }}</ref> 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 ] and ] effects of cannabis,<ref>{{cite journal | vauthors = Burstein SH, Hull K, Hunter SA, Latham V | title = Cannabinoids and pain responses: a possible role for prostaglandins | journal = FASEB Journal | volume = 2 | issue = 14 | pages = 3022–3026 | date = November 1988 | pmid = 2846397 | doi = 10.1096/fasebj.2.14.2846397 | doi-access = free | s2cid = 46552755 }}</ref><ref>{{cite journal | vauthors = Doyle SA, Burstein SH, Dewey WL, Welch SP | title = Further studies on the antinociceptive effects of delta 6-THC-7-oic acid | journal = Agents and Actions | volume = 31 | issue = 1–2 | pages = 157–163 | date = August 1990 | pmid = 2178317 | doi = 10.1007/bf02003237 | s2cid = 23310488 }}</ref><ref>{{cite journal | vauthors = Ujváry I, Grotenhermen F | title = 11-Nor-9-carboxy-Δ9-tetrahydrocannabinol – a ubiquitous yet underresearched cannabinoid. A review of the literature | journal = Cannabinoids | volume = 9 | issue = 1 | pages = 1–8 | year = 2014 | url = http://www.cannabis-med.org/data/pdf/en_2014_01_1.pdf | access-date = 2014-06-25 | archive-date = 2017-04-20 | archive-url = https://web.archive.org/web/20170420192452/http://www.cannabis-med.org/data/pdf/en_2014_01_1.pdf | url-status = dead }}</ref> 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.<ref>{{cite journal | vauthors = Burstein S, Hunter SA, Latham V, Renzulli L | title = A major metabolite of delta 1-tetrahydrocannabinol reduces its cataleptic effect in mice | journal = Experientia | volume = 43 | issue = 4 | pages = 402–403 | date = April 1987 | pmid = 3032669 | doi = 10.1007/BF01940427 | s2cid = 22153383 }}</ref><ref>{{cite journal | vauthors = Burstein S, Hunter SA, Latham V, Renzulli L | title = Prostaglandins and cannabis--XVI. Antagonism of delta 1-tetrahydrocannabinol action by its metabolites | journal = Biochemical Pharmacology | volume = 35 | issue = 15 | pages = 2553–2558 | date = August 1986 | pmid = 3017356 | doi = 10.1016/0006-2952(86)90053-5 }}</ref> |
|
|
|
|
|
== Legal status == |
|
|
The legal status of 11-nor-9-carboxy-THC varies among jurisdictions. |
|
|
|
|
|
=== Australia === |
|
|
11-COOH-THC is a ] prohibited substance in ] under the ] (July 2016).<ref name="Poisons Standard">Poisons Standard July 2016 </ref> 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.<ref name="Poisons Standard" /> |
|
|
|
|
|
===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 ]. |
|
|
|
|
|
== See also == |
|
|
* ], a synthetic analog of 11-nor-9-carboxy-THC |
|
|
* ] |
|
|
|
|
|
== References == |
|
|
{{Reflist}} |
|
|
|
|
|
{{Cannabinoids}} |
|
|
{{Cannabinoidergics}} |
|
|
|
|
|
{{DEFAULTSORT:Nor-9-carboxy-THC, 11-}} |
|
|
] |
|
|
] |
|
|
] |
|
|
] |
|
|
] |
|
|
] |
|
|
] |