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

CCCCCC1=CC(O)=C2[C@@H]3C=C(CC[C@H]3C(C)(C)OC2=C1)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 1447
Arachidonate 15-lipoxygenase 6 Target ID: CHEMBL2903 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20891010	Inhibitor 8504
Arachidonate 5-lipoxygenase 52 Target ID: CHEMBL215 Sources: http://www.cannabis-med.org/index.php?tpl=cannabinoids&id=281&lng=en&red=cannabinoidslist	Inhibitor 8504

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 1147	Unknown Approved Use Unknown
Pain 619 Sources: http://www.cannabis-med.org/index.php?tpl=cannabinoids&id=281&lng=en&red=cannabinoidslist	Primary	Preclinical	Unknown Approved Use Unknown
Atherosclerosis 76 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

C_max

Value	Dose	Analyte	Population
1.013 ng/mL CLINICAL TRIAL https://karger.com/mca/article/1/1/44/189041	1.25 mg 1 times / day multiple, rectal dose: 1.25 mg route of administration: Rectal experiment type: MULTIPLE co-administered:	DRONABINOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
0.953 ng/mL CLINICAL TRIAL https://karger.com/mca/article/1/1/44/189041	2.5 mg 1 times / day multiple, rectal dose: 2.5 mg route of administration: Rectal experiment type: MULTIPLE co-administered:	DRONABINOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
2.431 ng/mL CLINICAL TRIAL https://karger.com/mca/article/1/1/44/189041	5 mg 1 times / day multiple, rectal dose: 5 mg route of administration: Rectal experiment type: MULTIPLE co-administered:	DRONABINOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
3.977 ng/mL CLINICAL TRIAL https://karger.com/mca/article/1/1/44/189041	10 mg 1 times / day multiple, rectal dose: 10 mg route of administration: Rectal experiment type: MULTIPLE co-administered:	DRONABINOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
7.666 ng/mL CLINICAL TRIAL https://karger.com/mca/article/1/1/44/189041	20 mg 1 times / day multiple, rectal dose: 20 mg route of administration: Rectal experiment type: MULTIPLE co-administered:	DRONABINOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
6.57 ng/mL CLINICAL TRIAL https://karger.com/mca/article/1/1/44/189041	10 mg 1 times / day multiple, rectal dose: 10 mg route of administration: Rectal experiment type: MULTIPLE co-administered:	DRONABINOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
9.21 ng/mL CLINICAL TRIAL https://karger.com/mca/article/1/1/44/189041	10 mg 1 times / day multiple, oral dose: 10 mg route of administration: Oral experiment type: MULTIPLE co-administered:	DRONABINOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
1.23 ng/mL CLINICAL TRIAL https://www.tandfonline.com/doi/full/10.2147/CPAA.S119676	4.25 mg single, oral dose: 4.25 mg route of administration: Oral experiment type: SINGLE co-administered:	DRONABINOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
2.16 ng/mL CLINICAL TRIAL https://www.tandfonline.com/doi/full/10.2147/CPAA.S119676	5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered:	DRONABINOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
3.12 ng/mL CLINICAL TRIAL https://www.tandfonline.com/doi/full/10.2147/CPAA.S119676	5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered:	DRONABINOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
1.32 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/018651s029lbl.pdf	2.5 mg single, oral dose: 2.5 mg route of administration: Oral experiment type: SINGLE co-administered:	DRONABINOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
2.96 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/018651s029lbl.pdf	5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered:	DRONABINOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
7.88 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/018651s029lbl.pdf	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:	DRONABINOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

AUC

Value	Dose	Analyte	Population
20.318 ng × h/mL CLINICAL TRIAL https://karger.com/mca/article/1/1/44/189041	5 mg 1 times / day multiple, rectal dose: 5 mg route of administration: Rectal experiment type: MULTIPLE co-administered:	DRONABINOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
33.621 ng × h/mL CLINICAL TRIAL https://karger.com/mca/article/1/1/44/189041	10 mg 1 times / day multiple, rectal dose: 10 mg route of administration: Rectal experiment type: MULTIPLE co-administered:	DRONABINOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
79.954 ng × h/mL CLINICAL TRIAL https://karger.com/mca/article/1/1/44/189041	20 mg 1 times / day multiple, rectal dose: 20 mg route of administration: Rectal experiment type: MULTIPLE co-administered:	DRONABINOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
47.84 ng × h/mL CLINICAL TRIAL https://karger.com/mca/article/1/1/44/189041	10 mg 1 times / day multiple, rectal dose: 10 mg route of administration: Rectal experiment type: MULTIPLE co-administered:	DRONABINOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
19.59 ng × h/mL CLINICAL TRIAL https://karger.com/mca/article/1/1/44/189041	10 mg 1 times / day multiple, oral dose: 10 mg route of administration: Oral experiment type: MULTIPLE co-administered:	DRONABINOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
13.29 ng × h/mL CLINICAL TRIAL https://www.tandfonline.com/doi/full/10.2147/CPAA.S119676	4.25 mg single, oral dose: 4.25 mg route of administration: Oral experiment type: SINGLE co-administered:	DRONABINOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
15.59 ng × h/mL CLINICAL TRIAL https://www.tandfonline.com/doi/full/10.2147/CPAA.S119676	5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered:	DRONABINOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
11.81 ng × h/mL CLINICAL TRIAL https://www.tandfonline.com/doi/full/10.2147/CPAA.S119676	5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered:	DRONABINOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
2.88 ng × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/018651s029lbl.pdf	2.5 mg single, oral dose: 2.5 mg route of administration: Oral experiment type: SINGLE co-administered:	DRONABINOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
6.16 ng × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/018651s029lbl.pdf	5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered:	DRONABINOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
15.2 ng × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/018651s029lbl.pdf	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:	DRONABINOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

T_1/2

Value	Dose	Analyte	Population
11.23 h CLINICAL TRIAL https://www.tandfonline.com/doi/full/10.2147/CPAA.S119676	4.25 mg single, oral dose: 4.25 mg route of administration: Oral experiment type: SINGLE co-administered:	DRONABINOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
11.11 h CLINICAL TRIAL https://www.tandfonline.com/doi/full/10.2147/CPAA.S119676	5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered:	DRONABINOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
12.47 h CLINICAL TRIAL https://www.tandfonline.com/doi/full/10.2147/CPAA.S119676	5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered:	DRONABINOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
64 h CLINICAL TRIAL https://watermark.silverchair.com/28-3-160.pdf	7.5 mg 1 times / day multiple, oral dose: 7.5 mg route of administration: Oral experiment type: MULTIPLE co-administered:	DRONABINOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED
52.1 h CLINICAL TRIAL https://watermark.silverchair.com/28-3-160.pdf	14.8 mg 1 times / day multiple, oral dose: 14.8 mg route of administration: Oral experiment type: MULTIPLE co-administered:	DRONABINOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED
44.2 h CLINICAL TRIAL https://watermark.silverchair.com/28-3-160.pdf	0.47 mg 1 times / day multiple, oral dose: 0.47 mg route of administration: Oral experiment type: MULTIPLE co-administered:	DRONABINOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED
50.3 h CLINICAL TRIAL https://watermark.silverchair.com/28-3-160.pdf	0.39 mg 1 times / day multiple, oral dose: 0.39 mg route of administration: Oral experiment type: MULTIPLE co-administered:	DRONABINOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED
25 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/018651s029lbl.pdf	2.5 mg single, oral dose: 2.5 mg route of administration: Oral experiment type: SINGLE co-administered:	DRONABINOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
36 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/018651s029lbl.pdf	5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered:	DRONABINOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
36 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/018651s029lbl.pdf	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:	DRONABINOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

F_unbound

Value	Dose	Co-administered	Analyte	Population
10% CLINICAL TRIAL https://www.sciencedirect.com/science/article/abs/pii/S0379073801005382	single, unknown		DRONABINOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	UGT2B7 456 UGT2B15 236 UGT1A7 249 UGT2B17 237 UGT1A8 323 UGT1A1 479 UGT1A9 423 UGT1A3 470 UGT1A4 399 UGT1A10 331 UGT1A6 343 UGT2B4 278

Drug as victim

Target	Modality	Activity
UGT1A1 479	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/19339377/	moderate [Km 170 uM]
UGT1A10 331	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/19339377/	no
UGT1A8 323	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/19339377/	no
UGT1A9 423	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/19339377/	no
UGT2B15 236	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/19339377/	no
UGT2B17 237	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/19339377/	no
UGT2B4 278	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/19339377/	no
UGT2B7 456	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/19339377/	no
UGT1A3 470	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/19339377/	strong [Km 68 uM]
UGT1A4 399	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/19339377/	weak
UGT1A6 343	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/19339377/	weak
UGT1A7 249	substrate 4014 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 association of cannabis use on inpatient psychiatric hospital outcomes.	2018	28613973
11-nor-9-carboxy-Δ9-tetrahydrocannabinol glucuronide exhibits acyl-migration isomers.	2017-11-30	28892757
Improving wastewater-based epidemiology to estimate cannabis use: focus on the initial aspects of the analytical procedure.	2017-10-02	28916100
Maternal marijuana use, adverse pregnancy outcomes, and neonatal morbidity.	2017-10	28578174
Chlorination Kinetics of 11-Nor-9-carboxy-Δ9-tetrahydrocannabinol: Effects of pH and Humic Acid.	2017-09-19	28806081
Concentrations of delta9-tetrahydrocannabinol and 11-nor-9-carboxytetrahydrocannabinol in blood and urine after passive exposure to Cannabis smoke in a coffee shop.	2010-05	20465865
Urinary excretion profiles of 11-nor-9-carboxy-delta 9-tetrahydrocannabinol in humans after single smoked doses of marijuana.	1996-10	8889681
Marijuana metabolites in urine of man. X. Identification of marijuana use by detection of delta 9-tetrahydrocannabinol-11-oic acid using thin-layer chromatography.	1982-01-01	6276425
The tetrahydrocannabinol and tetrahydrocannabinolic acid content of cannabis products.	1981-06	6115009

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 `Mon Mar 31 18:15:21 GMT 2025` Edited by `admin` on `Mon Mar 31 18:15:21 GMT 2025`
Record UNII	4TPC9E4A32
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

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

Preferred Name

English

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

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