104874-50-2

Basic information

• Product Name: (+/-)-11-NOR-9-CARBOXY-DELTA9-THC
• Synonyms: (+/-)-11-NOR-9-CARBOXY-DELTA9-THC;11-NOR-DELTA(9)-TETRAHYDROCANNABINOL-9-CARBOXYLIC ACID;11-CARBOXY-DELTA(9)-TETRAHYDROCANNABINOL;11-nor-9-carboxy-delta9-tetrahydrocannabinol;Methanol(test (±)-11-Nor-9-Carboxy-delta-9-THC,100ug/mL);(±)-11-nor-9-Carboxy-δ9-THC (Racemic mixture - not to be used for immunoassay);DL-11-NOR-9-CARBOXY-DELTA 9;(+/-)-11-Nor-Δ9-Tetrahydrocannabinol
• CAS NO: 104874-50-2
• Molecular Formula: C₂₁H₂₈O₄
• Molecular Weight: 344.44
• EINECS: 200-659-6
• Mol File: 104874-50-2.mol
• Article Data: 8

Chemical Properties

• Melting Point: 174-176 °C
• Boiling Point: 466.9±45.0 °C(Predicted)
• Flash Point: 9℃
• Appearance: /vacuum-dried powder
• Density: 1.140±0.06 g/cm3(Predicted)
• Storage Temp.: −20°C
• PKA: 4.66±0.40(Predicted)
• CAS DataBase Reference: (+/-)-11-NOR-9-CARBOXY-DELTA9-THC(CAS DataBase Reference)
• NIST Chemistry Reference: (+/-)-11-NOR-9-CARBOXY-DELTA9-THC(104874-50-2)
• EPA Substance Registry System: (+/-)-11-NOR-9-CARBOXY-DELTA9-THC(104874-50-2)

Safety Data

• Hazard Codes: F,T
• Statements: 11-23/24/25-39/23/24/25
• Safety Statements: 7-16-36/37-45
• RIDADR: UN1230 - class 3 - PG 2 - Methanol, solution
• WGK Germany: 3
• Hazardous Substances Data: 104874-50-2(Hazardous Substances Data)

Usage

Description

(+/-)-11-NOR-9-CARBOXY-DELTA9-THC, also known as THC acid or 11-nor-9-carboxy-Δ9-THC, is a certified solution standard at a higher concentration of 1.0 mg/mL. It is the main secondary metabolite of THC found in the urine or blood of Cannabis users. (+/-)-11-NOR-9-CARBOXY-DELTA9-THC is structurally categorized as a cannabinoid metabolite and is produced by the oxidation of the primary metabolite 11-hydroxy-Δ9-THC. It is suitable for use in various applications, including forensic analysis, urine drug testing, and clinical toxicology.

Uses

Used in Forensic Analysis:
(+/-)-11-NOR-9-CARBOXY-DELTA9-THC is used as a certified reference material for forensic applications. It aids in the preparation of calibrators and controls for THC testing by GC/MS or LC/MS, helping to accurately identify and quantify the presence of THC in biological samples.
Used in Urine Drug Testing:
In the application industry of urine drug testing, (+/-)-11-NOR-9-CARBOXY-DELTA9-THC is used as a starting material for the development of testing protocols and reference materials. This helps in the detection and quantification of THC metabolites in urine samples, providing valuable information for assessing an individual's cannabis use.
Used in Clinical Toxicology:
(+/-)-11-NOR-9-CARBOXY-DELTA9-THC is utilized as a certified reference material in clinical toxicology. It is essential for the development and validation of testing methods to determine the presence and concentration of THC metabolites in biological samples, which can be crucial in cases of suspected drug overdose or intoxication.
Used in Research:
In the research industry, (+/-)-11-NOR-9-CARBOXY-DELTA9-THC is used as a certified reference material for studying the properties, metabolism, and effects of THC and its metabolites. This helps researchers gain a deeper understanding of the compound's role in various physiological and psychological processes, as well as its potential therapeutic applications.

Upstream product

• 123408-92-4 (6aR,10aR)-9-[1,3]Dithian-2-yl-6,6-dimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromen-1-ol 
• 138285-36-6 (-)-11-oxo-Δ⁹-tetrahydrocannabinol tert-butyldimethylsilyl ether 
• 52663-85-1 (6aR,10aR)-1-Hydroxy-6,6-dimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromene-9-carbaldehyde 
• 124588-22-3 [(6aR,10aR)-1-(tert-Butyl-dimethyl-silanyloxy)-6,6-dimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromen-9-yl]-methanol 
• 6616-69-9 dl-6aα,7,10,10aα-Tetrahydro-1-hydroxy-6,6-dimethyl-3-pentyl-6H-dibenzo[b,d]pyran-9(8H)-on 
• 52195-11-6 (-)-9-Nor-9-oxohexahydrocannabinol 
• 124-38-9 carbon dioxide 
• 949595-94-2 C₃₅H₅₂N₂O₄S 
• 138285-38-8 (-)-11-nor-9-carboxy-Δ⁹-tetrahydrocannabinol tert-butyldimethylsilyl ether 
• 1972-08-3 dronabinol 
• 136954-91-1 (+/-)-11-oxo-Δ⁹-tetrahydrocannabiol tert-butyldimethylsilyl ether 
• 52663-85-1 11-oxo-6a,10a-trans-Δ⁹-THC 
• 16849-41-5 1-Hydroxy-3-pentyl-6,6a,7,8-tetrahydro-6,6-dimethyl-9H-dibenzopyran-9-one 
• 122700-18-9 1-(2,6-Dimethoxy-4-pentyl-phenyl)-6-(1-methoxy-1-methyl-ethyl)-cyclohex-2-enol 

Downstream Products

• 848242-78-4 C₂₅H₃₁NO₆ 

Relevant articles and documents

A concise methodology for the synthesis of (-)-Δ9-tetrahydrocannabinol and (-)-Δ9-tetrahydrocannabivarin metabolites and their regiospecifically deuterated analogs

The availability of tetrahydrocannabinols (Δ9-THC), tetrahydrocannabivarins (Δ9-THCV), and their metabolites in both their undeuterated and deuterated forms is critical for the analysis of biological and toxicological samples. We report here a concise methodology for the syntheses of (-)-Δ9-THC and (-)-Δ9-THCV metabolites in significantly improved overall yields using commercially available starting materials. Our approach allowed us to obtain the key intermediates (6aR,10aR)-9-nor-9-oxo-hexahydrocannabinols in four steps from (+)-(1R)-nopinone. This was followed by an optimized Shapiro reaction to give the (-)-11-nor-9-carboxy-metabolites, which were converted to their respective (-)-11-hydroxy analogs. The synthetic sequence involves a minimum number of steps, avoids undesirable oxidative conditions, and incorporates the costly deuterated resorcinols near the end of the synthetic sequence. This methodology enabled us to synthesize eight regiospecifically deuterated (-)-Δ9-THC and (-)-Δ9-THCV metabolites in a preparative scale and high optical purity without deuterium scrambling or loss.

Preparation of Racemic, (-)- And (+)-11-Nor-δ9-Tetrahydrocannabinol-9-carboxylic Acid

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Synthesis of (+/-)-11-Nor-9-carboxy-Δ9-tetrahydrocannabinol: New Synthetic Approaches to Cannabinoids

A completely regioselective synthesis of (+/-)-11-nor-9-carboxy-Δ9-tetrahydrocannabinol (1), a principal human metabolite of Δ9-tetrahydrocannabinol (2), has been carried out in seven steps and 14percent overall yield from apoverbene (9) and the bis-MOM ether of olivetol.Condensation of 9 with the aryllithium derived from the bis-MOM ether of olivetol gives an unstable tertiary allylic alcohol that undergoes oxidative rearrangement to give enone 42.Reaction of 42 with acid results in hydrolysis of the MOM ethers and cyclization to benzopyranone 21.Conversion to MOM ether 39 followed by Li/NH3 reduction and trapping of the enolate with N-phenyltriflimide gives vinyl triflate 40 plus the isomer with a cis ring fusion.Palladium-catalyzed carboxylation, hydrolysis of the MOM ether, and separation from cis acid 41 gives pure 1.Model experiments employing unsubstituted resorcinol derivatives that lead to ester 27 are described, as are a number of alternative approaches to acid 1.