1432794-98-3

Basic information

• Product Name: 1-(5-fluoropentyl)-1H-indole-3-carboxylic acid
• Synonyms: 1-(5-fluoropentyl)-1H-indole-3-carboxylic acid;5-fluoro PB-22 3-carboxyindole metabolite
• CAS NO: 1432794-98-3
• Molecular Formula: C14H16FNO2
• Molecular Weight: 249.2807432
• EINECS: -0
• Mol File: 1432794-98-3.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• Storage Temp.: -20°C
• CAS DataBase Reference: 1-(5-fluoropentyl)-1H-indole-3-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(5-fluoropentyl)-1H-indole-3-carboxylic acid(1432794-98-3)
• EPA Substance Registry System: 1-(5-fluoropentyl)-1H-indole-3-carboxylic acid(1432794-98-3)

Safety Data

• RIDADR: UN 1648 3 / PGII
• Hazardous Substances Data: 1432794-98-3(Hazardous Substances Data)

Usage

Description

1-(5-fluoropentyl)-1H-indole-3-carboxylic acid, also known as 5-Fluoro PB-22 3-carboxyindole, is a major metabolite of the synthetic cannabinoid 5-Fluoro PB-22. It is a compound with potential applications in various fields, including drug testing, forensic analysis, and clinical toxicology.

Uses

Used in Urine Drug Testing:
1-(5-fluoropentyl)-1H-indole-3-carboxylic acid is used as a starting material for calibrators or controls in synthetic cannabinoid GC/MS or LC/MS methods for urine drug testing. It helps in the accurate detection and quantification of synthetic cannabinoids in urine samples.
Used in Forensic Analysis:
In forensic analysis, 1-(5-fluoropentyl)-1H-indole-3-carboxylic acid is used as a reference compound for the identification and quantification of synthetic cannabinoids in various samples, such as blood, tissue, or hair. This aids in criminal investigations and legal proceedings.
Used in Clinical Toxicology Applications:
1-(5-fluoropentyl)-1H-indole-3-carboxylic acid is used as a certified Snap-N-Spike solution in clinical toxicology applications. It serves as a reference material for the development and validation of analytical methods to detect and measure synthetic cannabinoids in biological samples, which is crucial for understanding their toxicological effects and potential health risks.
Used in Regulatory Compliance:
For synthetic cannabinoids that are controlled at the federal level, 1-(5-fluoropentyl)-1H-indole-3-carboxylic acid is used as a DEA-exempt certified solution standard. This allows laboratories to order and use the compound without additional regulatory paperwork, streamlining the process for research and analysis.

Upstream product

• 120-72-9 indole 
• 407-97-6 1-bromo-5-fluoropentane 
• 1859218-30-6 N-fluoropentyl indole 
• 942-24-5 3-methoxycarbonylindole 
• 776-41-0 indole-3-carboxylic acid ethyl ester 

Relevant articles and documents

Evidence of enzyme-mediated transesterification of synthetic cannabinoids with ethanol: potential toxicological impact

Purpose: Synthetic cannabinoids (SCs) represent a large proportion of novel psychoactive substances on the black market and have caused a number of deaths. Polydrug use including combination of SCs and ethanol could further complicate the toxicological impact. To the best of our knowledge, there have been no reports presenting evidence of transesterification between SCs and ethanol in vitro. Methods: The in vitro metabolism of the four carboxylate SCs PB-22, NPB-22, 5-fluoro-PB-22 (5F-PB-22), and 5-fluoro-NPB-22 (5F-NPB-22) in the presence of ethanol using human liver microsomes with and without appropriate enzyme inhibitors was studied. Newly identified SC ethyl esters were chemically synthesised and fully characterised. The activity of these SCs and their ethanol transesterification products were assessed using cannabinoid receptor (CB1 and CB2) activation assays. Results: SCs/ethanol transesterification products were detected and studied using liquid chromatography–high-resolution mass spectrometry. We have shown that the SC ethyl ester formation is mediated by human carboxyl esterase enzymes. The ethyl esters exhibited a reduced activity for the CB receptors compared with their parent compounds. Conclusions: These novel ethyl esters may be useful additional markers of cannabinoid administration, and especially so if they prove to have longer half-lives than their parent compounds.

Synthesis method of 5F-EMB-PICA

The invention discloses a synthesis method of 5F-EMB-PICA as shown in a formula I in the specification. The method comprises the following steps: 1) with indole as a precursor, adding 1-bromo-5-fluoropentane and trifluoroacetic anhydride for a reaction to obtain an intermediate 1 as shown in a formula II; 2) subjecting the intermediate shown in the formula II to reacting under the action of alkali to obtain an intermediate 2 shown in a formula III; and 3) in the presence of alkali and a condensing agent, carrying out an amide condensation reaction on the intermediate 2 shown in the formula III and valine ethyl ester to obtain the 5F-EMB-PICA. The 5F-EMB-PICA prepared by the method disclosed by the invention is subjected to column chromatography and recrystallization treatment, and has purity of greater than 97% and total yield of 38.7%.

Evaluation of carboxamide-type synthetic cannabinoids on the functional activities at cannabinoid receptors and biological effects via inhalation exposure test

Purpose: Three synthetic carboxamide-type cannabinoids (5F-MDMB-PICA, 5F-EMB-PINACA, and AMB-CHMICA) were evaluated in terms of their in vitro activities at the cannabinoid receptors CB1 and CB2 and in vivo biological effects when smoking the synthetic cannabinoids to assess their biological effects. Methods: [35S]Guanosine-5′-O-(3-thio)-triphosphate binding assays were performed to investigate the half maximal effective concentration values of the test compounds at the CB1 and CB2 receptors. Additionally, the biological effects were evaluated by observing and scoring the behavior of mice with equipment in which they inhaled smoke from a herbal mixture containing the test compounds. Results: All three synthetic cannabinoids tested in this study activated the CB1 and CB2 receptors in vitro. 5F-MDMB-PICA showed less than 1?nM of the half maximal effective concentration value for both receptors. Therefore, it was suggested that 5F-MDMB-PICA was the strongest CB1 and CB2 receptor agonist in comparison with synthetic cannabinoids evaluated in the past. The degree of the various biological effects, specifically passivity, spontaneous activity, abnormal gait, abnormal position, and grip strength, when smoking the synthetic cannabinoids corresponded to the functional activity at the CB1 receptor. However, some biological effects differed between 5F-MDMB-PICA and 5F-MDMB-PINACA, used as a positive control, and AMB-CHMICA induced some biological effects in contrast to the other tested synthetic cannabinoids. Conclusion: This study provides information regarding the biological effects when smoking synthetic cannabinoids from the functional activities at the CB1 and CB2 receptors, considering their way of inhalation and thermal degradation.