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

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Downstream Products

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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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Studies on the synthesis of (-)-11-nor-9-carboxy-Δ9-tetrahydrocannabinol (THC) and related compounds: An improved oxidative procedure

A facile procedure is described whereby Δ9-THC aldehydes 4, as their tert-butyldimethylsilyl derivatives, are conveniently oxidized to the corresponding acids with sodium chlorite in the presence of a large excess of 2-methyl-2-butene without isomerization of the Δ9-double bond. Deprotection of the O-protecting group with tetrabutylammonium fluoride in tetrahydrofuran gave the acids 2 in an overall yield of ≥80%. A study of other oxidizing agents and protecting groups demonstrated that this is the procedure of choice for the preparation of 9-carboxy-Δ9-tetrahydrocannabinols.