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Details

Stereochemistry ABSOLUTE
Molecular Formula C21H28O4
Molecular Weight 344.4454
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

CCCCCc1cc(c2[C@]3([H])C=C(CC[C@@]3([H])C(C)(C)Oc2c1)C(=O)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 344.4454
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

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

Curator's Comment:: Known to be CNS penetrant in mouse. Human data not available. Only a negligible fraction (0.2%) of injected THC-COOH reached the brain.

Approval Year

PubMed

PubMed

TitleDatePubMed
The tetrahydrocannabinol and tetrahydrocannabinolic acid content of cannabis products.
1981 Jun
Patents

Sample Use Guides

Single dose of 5 mg THCCOOH.
Route of Administration: Intravenous
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 Jun 25 23:20:49 UTC 2021
Edited
by admin
on Fri Jun 25 23:20:49 UTC 2021
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
CAS
56354-06-4
Created by admin on Fri Jun 25 23:20:49 UTC 2021 , Edited by admin on Fri Jun 25 23:20:49 UTC 2021
PRIMARY
FDA UNII
4TPC9E4A32
Created by admin on Fri Jun 25 23:20:49 UTC 2021 , Edited by admin on Fri Jun 25 23:20:49 UTC 2021
PRIMARY
EPA CompTox
56354-06-4
Created by admin on Fri Jun 25 23:20:49 UTC 2021 , Edited by admin on Fri Jun 25 23:20:49 UTC 2021
PRIMARY
PUBCHEM
108207
Created by admin on Fri Jun 25 23:20:49 UTC 2021 , Edited by admin on Fri Jun 25 23:20:49 UTC 2021
PRIMARY
EVMPD
SUB33435
Created by admin on Fri Jun 25 23:20:49 UTC 2021 , Edited by admin on Fri Jun 25 23:20:49 UTC 2021
PRIMARY
CAS
64280-14-4
Created by admin on Fri Jun 25 23:20:49 UTC 2021 , Edited by admin on Fri Jun 25 23:20:49 UTC 2021
SUPERSEDED
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