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

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	MOL RATIO 1 MOL RATIO (average)

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

Description

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	Activator 1,447
Arachidonate 15-lipoxygenase 6	Inhibitor 8,504
Arachidonate 5-lipoxygenase 52	Inhibitor 8,504

Conditions

Condition	Modality	Highest Phase	Product
Cannabis abuse 1	Diagnostic	Phase II 1,147	Unknown
Pain 619	Primary	Preclinical	Unknown
Atherosclerosis 76	Primary	Basic research	Unknown

C_max

Value	Dose	Analyte	Population
1.013 ng/mL	1.25 mg 1 times / day multiple, rectal	DRONABINOL plasma	Homo sapiens
0.953 ng/mL	2.5 mg 1 times / day multiple, rectal	DRONABINOL plasma	Homo sapiens
2.431 ng/mL	5 mg 1 times / day multiple, rectal	DRONABINOL plasma	Homo sapiens
3.977 ng/mL	10 mg 1 times / day multiple, rectal	DRONABINOL plasma	Homo sapiens
7.666 ng/mL	20 mg 1 times / day multiple, rectal	DRONABINOL plasma	Homo sapiens
6.57 ng/mL	10 mg 1 times / day multiple, rectal	DRONABINOL plasma	Homo sapiens
9.21 ng/mL	10 mg 1 times / day multiple, oral	DRONABINOL plasma	Homo sapiens
1.23 ng/mL	4.25 mg single, oral	DRONABINOL plasma	Homo sapiens
2.16 ng/mL	5 mg single, oral	DRONABINOL plasma	Homo sapiens
3.12 ng/mL	5 mg single, oral	DRONABINOL plasma	Homo sapiens
1.32 ng/mL	2.5 mg single, oral	DRONABINOL plasma	Homo sapiens
2.96 ng/mL	5 mg single, oral	DRONABINOL plasma	Homo sapiens
7.88 ng/mL	10 mg single, oral	DRONABINOL plasma	Homo sapiens

AUC

Value	Dose	Analyte	Population
20.318 ng × h/mL	5 mg 1 times / day multiple, rectal	DRONABINOL plasma	Homo sapiens
33.621 ng × h/mL	10 mg 1 times / day multiple, rectal	DRONABINOL plasma	Homo sapiens
79.954 ng × h/mL	20 mg 1 times / day multiple, rectal	DRONABINOL plasma	Homo sapiens
47.84 ng × h/mL	10 mg 1 times / day multiple, rectal	DRONABINOL plasma	Homo sapiens
19.59 ng × h/mL	10 mg 1 times / day multiple, oral	DRONABINOL plasma	Homo sapiens
13.29 ng × h/mL	4.25 mg single, oral	DRONABINOL plasma	Homo sapiens
15.59 ng × h/mL	5 mg single, oral	DRONABINOL plasma	Homo sapiens
11.81 ng × h/mL	5 mg single, oral	DRONABINOL plasma	Homo sapiens
2.88 ng × h/mL	2.5 mg single, oral	DRONABINOL plasma	Homo sapiens
6.16 ng × h/mL	5 mg single, oral	DRONABINOL plasma	Homo sapiens
15.2 ng × h/mL	10 mg single, oral	DRONABINOL plasma	Homo sapiens

T_1/2

Value	Dose	Analyte	Population
11.23 h	4.25 mg single, oral	DRONABINOL plasma	Homo sapiens
11.11 h	5 mg single, oral	DRONABINOL plasma	Homo sapiens
12.47 h	5 mg single, oral	DRONABINOL plasma	Homo sapiens
64 h	7.5 mg 1 times / day multiple, oral	DRONABINOL plasma	Homo sapiens
52.1 h	14.8 mg 1 times / day multiple, oral	DRONABINOL plasma	Homo sapiens
44.2 h	0.47 mg 1 times / day multiple, oral	DRONABINOL plasma	Homo sapiens
50.3 h	0.39 mg 1 times / day multiple, oral	DRONABINOL plasma	Homo sapiens
25 h	2.5 mg single, oral	DRONABINOL plasma	Homo sapiens
36 h	5 mg single, oral	DRONABINOL plasma	Homo sapiens
36 h	10 mg single, oral	DRONABINOL plasma	Homo sapiens

F_unbound

Value	Dose	Co-administered	Analyte	Population
10%	single, unknown		DRONABINOL plasma	Homo sapiens

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

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Target	Modality	Activity
UGT1A1 479	substrate 4,014	moderate [Km 170 uM]
UGT1A10 331	substrate 4,014	no
UGT1A8 323	substrate 4,014	no
UGT1A9 423	substrate 4,014	no
UGT2B15 236	substrate 4,014	no

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Sourcing

Sourcing

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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

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PubMed

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Title	Date	PubMed
Urinary excretion profiles of 11-nor-9-carboxy-delta 9-tetrahydrocannabinol in humans after single smoked doses of marijuana.	1996 Oct	8889681
11-nor-9-carboxy-Δ(9)-tetrahydrocannabinol glucuronide exhibits acyl-migration isomers.	2017 Nov 30	28892757
Improving wastewater-based epidemiology to estimate cannabis use: focus on the initial aspects of the analytical procedure.	2017 Oct 2	28916100
The association of cannabis use on inpatient psychiatric hospital outcomes.	2018	28613973

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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
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

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Code System

Code

Type

Description

WIKIPEDIA

11-Nor-9-carboxy-THC

PRIMARY

CAS

56354-06-4

PRIMARY

SMS_ID

100000126327

PRIMARY

FDA UNII

4TPC9E4A32

PRIMARY

PUBCHEM

108207

PRIMARY

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Related Record

Type

Details


					7J8897W37S

DRONABINOL

PARENT -> METABOLITE INACTIVE

Qualification:

URINE

Amount:

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SMILES

InChI

CNS Activity

Originator

Approval Year

Targets

Conditions

Cmax

AUC

T1/2

Funbound

Overview

OverviewOther

Drug as victim

Sourcing

PubMed

Patents

Sample Use Guides

C_max

T_1/2

F_unbound