11-NOR-9-CARBOXY-.DELTA.9-TETRAHYDROCANNABINOL

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C21H28O4
Molecular Weight	344.4446
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of 11-NOR-9-CARBOXY-.DELTA.9-TETRAHYDROCANNABINOL

Structure Search

SMILES

[H][C@@]12CCC(=C[C@@]1([H])C3=C(OC2(C)C)C=C(CCCCC)C=C3O)C(O)=O

InChI

InChIKey=YOVRGSHRZRJTLZ-HZPDHXFCSA-N

InChI=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)/t15-,16-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C21H28O4
Molecular Weight	344.4446
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: http://www.cannabis-med.org/index.php?tpl=cannabinoids&id=281&lng=en&red=cannabinoidslist | https://www.ncbi.nlm.nih.gov/pubmed/17906686 | https://www.ncbi.nlm.nih.gov/pubmed/16439618 | https://www.ncbi.nlm.nih.gov/pubmed/25220020

11-NOR-9-CARBOXY-DELTA9-TETRAHYDROCANNABINOL (THC-COOH) is the main the non-psychoactive metabolite of Delta9-Tetrahydrocannabinol. Being most abundant in bodily fluids, it has become an established marker of cannabis consumption in forensic, clinical and environmental analyses. Among the cannabinoids tested as potential inhibitors of the drug efflux transporter P-glycoprotein (Pgp), which is responsible for the multidrug-resistance of a tumour and normal cells, THC-COOH behaved as a substrate and was the most active in stimulating Pgp-dependent ATPase. It displayed analgesic and anti-inflammatory properties apparently by inhibiting cyclooxygenase and 5-lipoxygenase activities. THC-COOH was not an anxiolytic or anxiogenic drug but abolished the anxiogenic behavioral effect of Delta9-Tetrahydrocannabinol.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
P-glycoprotein 1 54 Target ID: CHEMBL4302 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16439618	Activator 1430
Arachidonate 15-lipoxygenase 6 Target ID: CHEMBL2903 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20891010	Inhibitor 8297
Arachidonate 5-lipoxygenase 49 Target ID: CHEMBL215 Sources: http://www.cannabis-med.org/index.php?tpl=cannabinoids&id=281&lng=en&red=cannabinoidslist	Inhibitor 8297

Conditions

Condition	Modality	Highest Phase	Product
Cannabis abuse 1 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20465865 https://www.ncbi.nlm.nih.gov/pubmed/8889681 https://www.ncbi.nlm.nih.gov/pubmed/18695931 https://www.ncbi.nlm.nih.gov/pubmed/22151583	Diagnostic	Phase II 1132	Unknown Approved Use Unknown
Pain 614 Sources: http://www.cannabis-med.org/index.php?tpl=cannabinoids&id=281&lng=en&red=cannabinoidslist	Primary	Preclinical	Unknown Approved Use Unknown
Atherosclerosis 74 Sources: http://www.cannabis-med.org/index.php?tpl=cannabinoids&id=281&lng=en&red=cannabinoidslist https://www.ncbi.nlm.nih.gov/pubmed/20891010	Primary	Basic research	Unknown Approved Use Unknown

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	UGT2B7 389 UGT2B15 203 UGT1A7 236 UGT2B17 213 UGT1A8 283 UGT1A1 418 UGT1A9 380 UGT1A3 422 UGT1A4 347 UGT1A10 291 UGT1A6 307 UGT2B4 249

Drug as victim

Target	Modality	Activity
UGT1A1 418	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/19339377/	moderate [Km 170 uM]
UGT1A10 291	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/19339377/	no
UGT1A8 283	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/19339377/	no
UGT1A9 380	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/19339377/	no
UGT2B15 203	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/19339377/	no
UGT2B17 213	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/19339377/	no
UGT2B4 249	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/19339377/	no
UGT2B7 389	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/19339377/	no
UGT1A3 422	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/19339377/	strong [Km 68 uM]
UGT1A4 347	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/19339377/	weak
UGT1A6 307	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/19339377/	weak
UGT1A7 236	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/19339377/	weak

Sourcing

Vendor/Aggregator	ID	URL
1PlusChem LLC	1P008RLS	https://www.1pchem.com/search?query=1P008RLS
Alfa Chemistry	64280-14-4	http://www.alfa-chemistry.com/search.aspx?q=64280-14-4
BOC Sciences	64280-14-4
Cayman Chemical	20754	http://www.caymanchem.com/app/template/Product.vm/catalog/20754
MuseChem	M117253	https://www.musechem.com/product/M117253.html
Sigma Aldrich	T-006	http://www.sigmaaldrich.com/catalog/search?term=T-006&interface=All&N=0&mode=match%20partialmax&lang=en®ion=US&focus=product
Tetrahedron	TS64436	http://www.thsci.com/search.do?q=TS64436
Toronto Research Chemicals	KIT8475	https://www.trc-canada.com/product-detail/?CatNum=KIT8475
Toronto Research Chemicals	N826250	https://www.trc-canada.com/product-detail/?CatNum=N826250

PubMed

Title	Date	PubMed
The tetrahydrocannabinol and tetrahydrocannabinolic acid content of cannabis products.	1981 Jun	6115009
Marijuana metabolites in urine of man. X. Identification of marijuana use by detection of delta 9-tetrahydrocannabinol-11-oic acid using thin-layer chromatography.	1982 Jan 1	6276425
Urinary excretion profiles of 11-nor-9-carboxy-delta 9-tetrahydrocannabinol in humans after single smoked doses of marijuana.	1996 Oct	8889681
Concentrations of delta9-tetrahydrocannabinol and 11-nor-9-carboxytetrahydrocannabinol in blood and urine after passive exposure to Cannabis smoke in a coffee shop.	2010 May	20465865
11-nor-9-carboxy-Δ(9)-tetrahydrocannabinol glucuronide exhibits acyl-migration isomers.	2017 Nov 30	28892757
Maternal marijuana use, adverse pregnancy outcomes, and neonatal morbidity.	2017 Oct	28578174
Improving wastewater-based epidemiology to estimate cannabis use: focus on the initial aspects of the analytical procedure.	2017 Oct 2	28916100
Chlorination Kinetics of 11-Nor-9-carboxy-Δ(9)-tetrahydrocannabinol: Effects of pH and Humic Acid.	2017 Sep 19	28806081

Patents

Sample Use Guides

In Vivo Use Guide

Single dose of 5 mg THCCOOH.

Route of Administration: Intravenous

In Vitro Use Guide

11-nor-9-carboxy-delta-9-tetrahydrocannabinol at concentrations 0.08, 0.4, 2, 10, 50 do not significantly increased the intracellular accumulation of the Abcg2/ABCG2 substrate, mitoxantrone (FLH-4) in the MEF3.8/ Bcrp1 A2 cell line in a dose-dependent manner.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:59:00 UTC 2023` Edited by `admin` on `Fri Dec 15 15:59:00 UTC 2023`
Record UNII	4TPC9E4A32
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

11-NOR-9-CARBOXY-.DELTA.9-TETRAHYDROCANNABINOL

Common Name

English

THC-COOH

Common Name

English

11-NOR-9-CARBOXY-9.DELTA.-TETRAHYDROCANNABINOL

Common Name

English

6H-DIBENZO(B,D)PYRAN-9-CARBOXYLIC ACID, 6A,7,8,10A-TETRAHYDRO-1-HYDROXY-6,6-DIMETHYL-3-PENTYL-, (6AR,10AR)-

Systematic Name

English

(-)-11-NOR-9-CARBOXY-.DELTA.9-THC

Common Name

English

ACIDE 11-NOR-DELTA-9-THC-CARBOXYLIQUE

Common Name

English

11-NOR-.DELTA.9-TETRAHYDROCANNABINOL-9-CARBOXYLIC ACID

Common Name

English

11-NOR-9-CARBOXY-DELTA-9-TETRAHYDROCANNABINOL

Common Name

English

ACIDE CANNABINOIQUE

Common Name

English

11-NOR-DELTA(9)-TETRAHYDROCANNABINOL-9-CARBOXYLIC ACID

Common Name

English

Code System Code Type Description

WIKIPEDIA

11-Nor-9-carboxy-THC