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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 51, 2021 - Issue 5
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Articles

Synthesis of nine potential synthetic cannabinoid metabolites with a 5F-4OH pentyl side chain from a scalable key intermediate

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Pages 776-785 | Received 15 Sep 2020, Published online: 29 Dec 2020

Figures & data

Figure 1. General structural information of synthetic cannabinoids with JWH-018 as an example, where the dotted lines are connected bonds. It was adopted from European Monitoring Center for Drugs and Drug Addiction (EMCDDA) and modified.[Citation14,Citation15]

Figure 1. General structural information of synthetic cannabinoids with JWH-018 as an example, where the dotted lines are connected bonds. It was adopted from European Monitoring Center for Drugs and Drug Addiction (EMCDDA) and modified.[Citation14,Citation15]

Scheme 1. Overview of synthesis of 5F-4OH synthetic cannabinoid metabolites.

Scheme 1. Overview of synthesis of 5F-4OH synthetic cannabinoid metabolites.

Scheme 2. Synthesis of the key intermediate 1.

Scheme 2. Synthesis of the key intermediate 1.

Scheme 3. Synthesis of nine potential 5F-4OH synthetic cannabinoid metabolites from key intermediate 1. General conditions: TBTU, TEA, amine/amino acid/alcohol, rt for 2 h to two nights or 65 °C for 2 h to five nights.

Scheme 3. Synthesis of nine potential 5F-4OH synthetic cannabinoid metabolites from key intermediate 1. General conditions: TBTU, TEA, amine/amino acid/alcohol, rt for 2 h to two nights or 65 °C for 2 h to five nights.

Figure 2. Chemical structures of the studied synthetic cannabinoids.

Figure 2. Chemical structures of the studied synthetic cannabinoids.
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