209414-07-3

Basic information

• Product Name: 1-Pentyl-3-(1-naphthoyl)indole
• Synonyms: 1-Pentyl-3-(1-naphthoyl)indole;Naphthalen-1-yl(1-Pentyl-1H-Indol-3-yl)Methanone;JWH -018;1-Naphthalenyl-(1-pentyl-1H-indol-3-yl)methanone;(1-Pentyl-1H-indol-3-yl)-1-naphthalenylmethanone;1-Pentyl-3-(1-naphthoyl)indole JWH 018;1-Naphthyl-(1-pentylindol-3-yl)Methanone;JWH-018 (Spice Cannabinoid)
• CAS NO: 209414-07-3
• Molecular Formula: C24H23NO
• Molecular Weight: 341.45
• EINECS: 200-659-6
• Product Categories: Aromatics;Heterocycles;Indole Derivatives;Intermediates & Fine Chemicals;Pharmaceuticals;Research Chemical;Chemical for Research;pharmaceutical intermediate and medicine grade
• Mol File: 209414-07-3.mol
• Article Data: 5

Chemical Properties

• Melting Point: 55-59°C
• Boiling Point: 534.2°C at 760 mmHg
• Flash Point: 9℃
• Appearance: /
• Density: 1.09g/cm³
• Vapor Pressure: 1.73E-11mmHg at 25°C
• Refractive Index: 1.605
• Storage Temp.: Desiccate at -20°C
• CAS DataBase Reference: 1-Pentyl-3-(1-naphthoyl)indole(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Pentyl-3-(1-naphthoyl)indole(209414-07-3)
• EPA Substance Registry System: 1-Pentyl-3-(1-naphthoyl)indole(209414-07-3)

Safety Data

• Hazard Codes: F,T
• Statements: 11-23/24/25-39/23/24/25-25
• Safety Statements: 7-16-36/37-45
• RIDADR: UN1230 - class 3 - PG 2 - Methanol, solution
• WGK Germany: 1
• Hazardous Substances Data: 209414-07-3(Hazardous Substances Data)

Usage

Description

JWH 018 (CRM) (Item No. 27973) is a certified reference material categorized as a synthetic cannabinoid. It has been found in Spice/K2-type herbal blends and may have neurotoxic properties. JWH 018 is regulated as a Schedule I compound in the United States. JWH 018 (CRM) (Item No. 27973) is provided as a DEA exempt preparation. This product is intended for research and forensic applications.

Chemical Properties

White Powder

Uses

Different sources of media describe the Uses of 209414-07-3 differently. You can refer to the following data:
1. Analgesic Drug
2. JWH 018 is the 18th compound synthesized in a series of more than 470 analogs and metabolites of ?9-Tetrahydro- cannabinol (THC) (T293200), the active component of marijuana. JWH 018 acts as cannabinoid receptor. Controlled substance.

Biological Activity

Potent cannabinoid receptor agonist with mild selectivity for CB 2 (K i values are 2.94 and 9.0 nM for CB 2 and CB 1 receptors respectively).

InChI:InChI=1/C24H23NO/c1-2-3-8-16-25-17-22(20-13-6-7-15-23(20)25)24(26)21-14-9-11-18-10-4-5-12-19(18)21/h4-7,9-15,17H,2-3,8,16H2,1H3

Upstream product

• 120-72-9 indole 
• 628-17-1 amyl iodide 
• 59529-21-4 1-pentyl-1H-indole 
• 879-18-5 naphthalene-1-carbonic acid chloride 
• 110-53-2 1-Bromopentane 
• 109555-87-5 (1H-indol-3-yl)(naphthalene-1-yl)methanone 
• 1226853-98-0 naphthalen-1-yl[1-(phenylsulfonyl)-1H-indol-3-yl]methanone 

Relevant articles and documents

Preparation of bivalent agonists for targeting the mu opioid and cannabinoid receptors

In order to obtain novel pharmacological tools and to investigate a multitargeting analgesic strategy, the CB1 and CB2 cannabinoid receptor agonist JWH-018 was conjugated with the opiate analgesic oxycodone or with an enkephalin related tetrapeptide. The opioid and cannabinoid pharmacophores were coupled via spacers of different length and chemical structure. In vitro radioligand binding experiments confirmed that the resulting bivalent compounds bound both to the opioid and to the cannabinoid receptors with moderate to high affinity. The highest affinity bivalent derivatives 11 and 19 exhibited agonist properties in [35S]GTPγS binding assays. These compounds activated MOR and CB (11 mainly CB2, whereas 19 mainly CB1) receptor-mediated signaling, as it was revealed by experiments using receptor specific antagonists. In rats both 11 and 19 exhibited antiallodynic effect similar to the parent drugs in 20 μg dose at spinal level. These results support the strategy of multitargeting G-protein coupled receptors to develop lead compounds with antinociceptive properties.

Visible-Light Photocatalytic Aerobic Benzylic C(sp3)?H Oxygenations with the 3DDQ*/tert-Butyl Nitrite Co-catalytic System

Photocatalytic aerobic benzylic C(sp3)?H oxygenations of aromatic hydrocarbons and C3-substituted indoles were studied by employing a co-catalytic system of 3DDQ* (DDQ=2,3-dichloro-5,6-dicyano-1,4-benzoquinone) and tert-butyl nitrite. The superior efficiency of these reaction conditions was demonstrated by comparison with the analogous thermal protocol, and a range of substrates could be oxidized catalytically and selectively in good yields.

One-pot desulfonylative alkylation of N-sulfonyl azacycles using alkoxides generated by phase-transfer catalysis

Sulfonamide heterocycles, specifically 3-acylindoles, undergo a deprotection/alkylation sequence in the presence of an appropriate alcohol when cesium carbonate or potassium carbonate and a phase-transfer catalyst are utilized. The outcome of the one-pot protocol was found to be significantly dependent on both the alcohol and sulfonamide heterocycle employed. Strictly anhydrous conditions are not necessary for this protocol. Georg Thieme Verlag Stuttgart · New York.