[1-(5-Fluoropentyl)-1H-indol-3-yl]-1-naphthalenylmethanone
[CAS# 335161-24-5]

Identification

• Classification: Organic raw materials >> Ketone compound
• Name: [1-(5-Fluoropentyl)-1H-indol-3-yl]-1-naphthalenylmethanone
• Synonyms: AM 2201
• Molecular Formula: C₂₄H₂₂FNO
• Molecular Weight: 359.44
• CAS Registry Number: 335161-24-5
• EC Number: 881-920-7
• SMILES: C1=CC=C2C(=C1)C=CC=C2C(=O)C3=CN(C4=CC=CC=C43)CCCCCF

Properties

• Density: 1.1±0.1 g/cm³ Calc.^*
• Boiling point: 551.1±30.0 °C 760 mmHg (Calc.)^*
• Flash point: 287.1±24.6 °C (Calc.)^*
• Index of refraction: 1.597 (Calc.)^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS06;GHS07 Danger
• Risk Statements: H301-H331-H336
• Safety Statements: P261-P264-P270-P271-P301+P316-P304+P340-P316-P319-P321-P330-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	3	H331
Acute toxicity	Acute Tox.	3	H301

Discovery and Applications

[1-(5-Fluoropentyl)-1H-indol-3-yl]-1-naphthalenylmethanone is a synthetic indole-based compound characterized by a 1H-indole core substituted at the nitrogen atom with a 5-fluoropentyl chain and at the 3-position with a naphthalenyl ketone group. Its molecular formula is C24H20FNO. The compound is lipophilic and generally appears as a solid or viscous oil, with solubility in organic solvents such as ethanol, methanol, and dimethyl sulfoxide, while being poorly soluble in water due to its hydrophobic aromatic structures.

The discovery of this compound is linked to the design of synthetic cannabinoids and related indole derivatives for research into receptor interactions and structure-activity relationships. The indole scaffold provides a versatile framework for modification, while the 5-fluoropentyl chain enhances lipophilicity and receptor binding, and the naphthalenylmethanone group contributes to electron density and steric interactions with cannabinoid receptors. Compounds of this type are used as tools in pharmacological studies of CB1 and CB2 receptors, as well as in the investigation of synthetic cannabinoid metabolism and toxicology.

Synthesis of [1-(5-fluoropentyl)-1H-indol-3-yl]-1-naphthalenylmethanone generally involves N-alkylation of indole with 5-fluoropentyl halides under basic conditions, followed by acylation at the 3-position using 1-naphthoyl chloride or equivalent reagents. Careful control of reaction conditions, including solvent choice, temperature, and reaction time, is required to achieve selective N-alkylation and 3-acylation without overreaction or side products. Purification is commonly performed by recrystallization or chromatography to isolate the target compound in high purity for experimental use.

Chemically, the compound exhibits typical reactivity of indole derivatives and ketones. The carbonyl group of the naphthalenylmethanone moiety can participate in nucleophilic addition, reduction, or condensation reactions, while the indole ring may undergo electrophilic substitution at available positions. The fluorinated pentyl chain affects both lipophilicity and metabolic stability, and it can influence receptor binding by increasing hydrophobic interactions within the active site. These chemical properties make the compound a valuable scaffold for structure-activity studies and the design of analogues with modified pharmacological profiles.

Pharmacologically, the compound functions as a cannabinoid receptor agonist. It interacts with CB1 and CB2 receptors in the central nervous system and peripheral tissues, modulating signaling pathways that affect neurotransmitter release, pain perception, and other physiological processes. Structural modifications, such as fluorination of the pentyl chain, increase receptor binding affinity and influence metabolic resistance, making it a useful model compound for studying the effects of synthetic cannabinoids on receptor selectivity and potency.

From a physical standpoint, the compound is generally stable under ambient laboratory conditions but should be protected from strong oxidizing agents and prolonged light exposure, which can lead to degradation of the indole or ketone functionalities. Handling precautions include avoiding inhalation, skin contact, and ingestion, as it may have potent biological activity.

Overall, [1-(5-fluoropentyl)-1H-indol-3-yl]-1-naphthalenylmethanone is a chemically and pharmacologically significant indole derivative. Its combination of a fluorinated pentyl chain, indole core, and naphthalenyl ketone provides a versatile scaffold for cannabinoid receptor research, structure-activity relationship studies, and the development of analogues with targeted biological properties. The compound exemplifies the use of synthetic modifications to tune receptor affinity, metabolic stability, and functional outcomes in pharmacological investigations.

References

2023. Effects of cannabinoid agonists and antagonists in male rats discriminating the synthetic cannabinoid AM2201. European Journal of Pharmacology.
DOI: 10.1016/j.ejphar.2023.176168

2023. MAM-2201 acute administration impairs motor, sensorimotor, prepulse inhibition, and memory functions in mice: a comparison with its analogue AM-2201. Psychopharmacology.
DOI: 10.1007/s00213-023-06378-8