Metabolite thc

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Metabolite THC: A Comprehensive Overview

Introduction to THC Metabolism

Delta-9-tetrahydrocannabinol (THC) is the primary psychoactive component of cannabis. Upon consumption, THC undergoes extensive metabolism, resulting in various metabolites that can be detected in different biological matrices. Understanding the metabolism of THC is crucial for both clinical and forensic applications.

Key Metabolites of THC

11-Hydroxy-THC (11-OH-THC)

11-Hydroxy-THC (11-OH-THC) is a significant psychoactive metabolite of THC. It is formed primarily through the action of the enzyme CYP2C9 in the liver 19. This metabolite is known for its potent psychoactive effects, which are comparable to those of THC itself. The formation and clearance of 11-OH-THC have been extensively studied, revealing that it is metabolized by both cytochrome P450 enzymes and UDP-glucuronosyltransferases (UGTs) 19.

THC-COOH and THC-COOH-Glucuronide

Another major metabolite is 11-nor-9-carboxy-THC (THC-COOH), which is inactive and is further conjugated to form THC-COOH-glucuronide (THC-COOH-Gluc). THC-COOH is the primary metabolite detected in urine and is used as a biomarker for cannabis consumption 26. The cross-reactivity of THC-COOH-Gluc in immunoassays is significant, as it can affect the accuracy of drug testing .

Metabolism in Different Tissues

Hepatic Metabolism

The liver is the primary site for THC metabolism. Enzymes such as CYP2C9, CYP3A4, and UGTs play crucial roles in the biotransformation of THC and its metabolites 19. The hepatic metabolism of THC involves both oxidative and conjugative pathways, leading to the formation of various metabolites, including 11-OH-THC and THC-COOH .

Extrahepatic Metabolism

THC and its metabolites are also metabolized in extrahepatic tissues such as the intestine, lung, and fetal liver. For instance, in the intestine, THC is primarily metabolized by CYP2C9 and CYP3A, while 11-OH-THC is metabolized by CYP3A and UGT2B7 . In fetal liver microsomes, CYP3A plays a dominant role in the metabolism of both THC and 11-OH-THC .

Detection and Analysis of THC Metabolites

Blood and Urine

The detection of THC and its metabolites in blood and urine is essential for understanding the pharmacokinetics and pharmacodynamics of cannabis. Studies have shown that THC levels peak rapidly after smoking and decline quickly, while metabolites like 11-OH-THC and THC-COOH have longer detection windows . Immunoaffinity extraction and gas chromatography-mass spectrometry (GC-MS) are commonly used techniques for analyzing these metabolites .

Hair and Oral Fluid

Hair analysis provides a long-term detection window for THC metabolites, with 11-nor-9-carboxy-THC (THC-COOH) being a key marker for cannabis use . In oral fluid, THC-COOH can also be detected, providing a non-invasive method for monitoring recent cannabis consumption .

Conclusion

The metabolism of THC involves complex pathways and results in various metabolites that can be detected in different biological matrices. Understanding these metabolic processes is crucial for both clinical and forensic applications, as it aids in the accurate detection and interpretation of cannabis use. Advances in analytical techniques continue to enhance our ability to study and understand the pharmacokinetics of THC and its metabolites.

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Most relevant research papers on this topic

Characterizing and Quantifying Extrahepatic Metabolism of (−)-Δ9-Tetrahydrocannabinol (THC) and Its Psychoactive Metabolite, (±)-11-Hydroxy-Δ9-THC (11-OH-THC)

THC and its psychoactive metabolite 11-OH-THC are metabolized in the intestinal and fetal liver, but not in adult lung, first trimester, or second trimester.

In Vitro Study

2022·

9citations

·Aditya R. Kumaret al.

Drug Metabolism and Disposition

Determination of the Cross-Reactivity of the Biological Metabolite (-)-trans-Δ9-Tetrahydrocannabinol-Carboxylic Acid-Glucuronide (THC-COOH-Gluc) for Cannabinoid Immunoassays.

The major metabolite of THC in urine is (-)-trans-THC-COOH-Gluc, with a cross-reactivity of 106-131% for cannabinoid immunoassays.

2020·

4citations

·K. E. Grafingeret al.

Journal of analytical toxicology

Synthesis of the Major Mammalian Metabolites of THCV.

This study successfully synthesized the major oxidized metabolites of THCV, including two new compounds and known compounds, without affecting the natural precursor's stereogenic center.

2020·

0citations

·Francesco Tintoet al.

Journal of natural products

Identification of in vivo liver metabolites of delta 6-tetrahydrocannabinol produced by the mouse.

Delta 6-tetrahydrocannabinol (THC) is metabolized in the mouse liver mainly through allylic and side-chain hydroxylation, with more extensive epoxide-diol pathway than delta 1-isomer.

In Vitro Study

1980·

10citations

·D. Harveyet al.

Drug metabolism and disposition: the biological fate of chemicals

Fast and highly sensitive determination of tetrahydrocannabinol (THC) metabolites in hair using liquid chromatography-multistage mass spectrometry (LC-MS3 ).

The developed LC-MS3 method effectively detects THC-COOH and 11-OH-THC in hair samples, providing reliable proof of cannabis consumption.

2022·

6citations

·Petra Hehetet al.

Drug testing and analysis

Detection of THCA in oral fluid by GC-MS-MS.

THCA is detectable in oral fluid samples from donors previously tested positive for THC, with concentrations ranging from 10 to 142 pg/mL.

2006·

53citations

·David Dayet al.

Journal of analytical toxicology

Simultaneous analysis of delta9-THC and its major metabolites in urine, plasma, and meconium by GC-MS using an immunoaffinity extraction procedure.

This study developed a simple extraction procedure for delta9-THC and its major metabolites in urine, plasma, and meconium, with high extraction recovery and linearity up to 100 ng/mL.

2000·

50citations

·S. Fenget al.

Journal of analytical toxicology

Blood cannabinoids. I. Absorption of THC and formation of 11-OH-THC and THCCOOH during and after smoking marijuana.

THC absorption during marijuana smoking leads to rapid peak levels of 11-OH-THC and slow peak levels of THCCOOH, impacting understanding of performance-impairing effects and aiding forensic interpretation of cannabinoid blood levels.

RCTHighly Cited

1992·

490citations

·M. Huestiset al.

Journal of analytical toxicology

Quantifying Hepatic Enzyme Kinetics of (-)-∆9-Tetrahydrocannabinol (THC) and Its Psychoactive Metabolite, 11-OH-THC, through In Vitro Modeling

The CYP2C9 pathway is the major pathway for depletion of THC and formation of 11-OH-THC, which can be used to predict THC and 11-OH-THC exposure in healthy and special populations.

In Vitro Study

2019·

23citations

·Gabriela I. Patilea-Vranaet al.

Drug Metabolism and Disposition

Comparative Metabolomic Profiling of the Metabolic Differences of Δ9-Tetrahydrocannabinol and Cannabidiol

Metabolomics reveals that THC metabolism differs from CBD metabolism, potentially impacting our understanding of THC-induced toxicity and drug safety.

In Vitro Study

2022·

3citations

·Qianru Raoet al.

Molecules

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