Thc chemical structure

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Chemical Structure of THC: A Comprehensive Overview

Introduction to THC Chemical Structure

Tetrahydrocannabinol (THC) is the primary psychoactive compound found in the Cannabis plant. The chemical structure of THC is crucial for understanding its pharmacological effects and interactions with cannabinoid receptors in the human body. This article synthesizes the latest research on the chemical structure of THC and its various isomers.

Delta-9-Tetrahydrocannabinol (Δ9-THC)

Molecular Structure and Crystallography

Delta-9-tetrahydrocannabinol (Δ9-THC) is the most well-known and studied isomer of THC. Its molecular structure is characterized by a tricyclic 21-carbon ring system with a pentyl side chain. The systematic name for Δ9-THC is (6aR,10aR)-6,6,9-trimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromen-1-ol . The crystal structure of Δ9-THC has been elucidated, revealing important details about its binding to cannabinoid receptors .

Receptor Binding and Activation

Δ9-THC binds to the cannabinoid receptor 1 (CB1), causing psychoactive effects. The binding induces significant conformational changes in the receptor, including a reduction in the volume of the ligand-binding pocket and an increase in the surface area of the G-protein-binding region . These structural changes are essential for receptor activation and the psychoactive effects of Δ9-THC.

Delta-8-Tetrahydrocannabinol (Δ8-THC)

Chemical Structure and Impurities

Delta-8-tetrahydrocannabinol (Δ8-THC) is another isomer of THC, differing from Δ9-THC by the position of a double bond. Δ8-THC has been identified in various commercial products, often containing several impurities. These impurities include Δ4,8-iso-tetrahydrocannabinol, Δ4-iso-tetrahydrocannabinol, and 8-hydroxy-iso-tetrahydrocannabinol, among others . The chemical structures of these impurities were determined using advanced spectroscopic methods such as NMR and GC-MS .

Synthesis and Usage

Δ8-THC is synthesized from cannabidiol (CBD) and is known for its less potent psychoactive effects compared to Δ9-THC. It is often used as a substitute for other substances and is readily accessible online . However, the lack of regulation in its synthesis can lead to contamination and inconsistent effects .

Other THC Isomers

Delta-10-Tetrahydrocannabinol (Δ10-THC)

Delta-10-tetrahydrocannabinol (Δ10-THC) is another isomer with distinct properties. Both trans- and cis-Δ10-THC isomers have been synthesized and studied for their receptor binding affinities. These isomers show strong affinity towards the CB1 receptor but do not exhibit the same psychoactive properties as Δ9-THC . Instead, they act as antagonists of the CB1 receptor, which is a unique functional property not observed in other THC isomers .

Hexahydrocannabinol (HHC) and Cannabinol (CBN)

Hexahydrocannabinol (HHC) and cannabinol (CBN) are other cannabinoids structurally related to THC. HHC is a hydrogenated derivative of THC, while CBN is a degradation product of THC. Both compounds have been studied for their structural and conformational properties, which influence their pharmacological activities .

Conclusion

The chemical structure of THC and its isomers plays a crucial role in their pharmacological effects and interactions with cannabinoid receptors. Δ9-THC remains the most studied isomer due to its potent psychoactive effects, while Δ8-THC and Δ10-THC offer alternative properties and potential therapeutic applications. Understanding the structural nuances of these compounds is essential for advancing cannabinoid research and developing new therapeutic agents.

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Most relevant research papers on this topic

Isolation and Characterization of Impurities in Commercially Marketed Δ8-THC Products.

This study identified 11 impurities in commercial 8-THC products, including 8-THCV, as well as other naturally occurring cannabinoids, as potential contaminants.

2023·

8citations

·M. Radwan et al.

Molecular structure and thermodynamic properties of the gaseous ThC2 and ThC4 species

The gaseous ThC2 and ThC4 molecules have asymmetric L-type structures and planar fan-type structures, respectively, with entropies comparable to experimental values.

2008·

15citations

·A. Kovács et al.

Structural studies of cannabinoids. A theoretical and proton magnetic resonance analysis.

This study provides structural information on cannabinoids, which may help understand their biological mode of action and potential therapeutic applications.

Highly Cited

1970·

76citations

·R. A. Archer et al.

Δ9-Tetrahydrocannabinolic acid A, the precursor to Δ9-tetrahydrocannabinol (THC).

THCA-A, the precursor to THC, has been successfully crystallized in the orthorhombic space group P212121, providing a standard point of departure for chemical and medical experiments.

2021·

1citation

·J. Skell et al.

The crystal structure of Th3B2C3

The crystal structure of Th3B2C3 reveals octahedra, tetrahedra, and trigonal prisms of Th-atoms, with boron atoms centered on Th-octahedra and carbon atoms Cl forming oc

1979·

25citations

·P. Rogl

A theoretical study for thorium monocarbide (ThC)

The study confirms that thorium monocarbide (ThC) with NaCl-type structure is mechanically stable and metallic, with consistent results from first-principles calculations and experimental results.

2012·

25citations

·S. Aydin et al.

Delta-8 tetrahydrocannabinol: A Scoping Review and Commentary.

Delta-8 THC is a less potent psychoactive substance, but its legality, accessibility, and marketing make it a potential risk to public health and safety.

Systematic Review

2023·

31citations

·C. LoParco et al.

Theoretical study of the structure and bonding in ThC2 and UC2.

The actinide dicarbides ThC2 and UC2 have energetically more favorable triangular structures, while linear and bent CAnC geometries are higher-energy structures.

2012·

29citations

·P. Pogány et al.

Crystal structures of agonist-bound human cannabinoid receptor CB1

The crystal structures of human CB1 reveal conformational changes and a 'twin toggle switch' essential for receptor activation, providing insights into the binding modes of 9-THC and other cannabinoids.

Very Rigorous JournalHighly Cited

2017·

378citations

·T. Hua et al.

Chemistry, Crystal Structure, and In Vitro Receptor Binding of Δ10-THC Isomers.

10-THC isomers show strong affinity for the CB1 receptor but lack THC-like psychoactivity, suggesting they are among antagonists of this receptor.

In Vitro Study

2023·

1citation

·Mehdi Haghdoost et al.

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