1-Pentyl-3-(1-naphthoyl)indole

Base Information

• Chemical Name: 1-Pentyl-3-(1-naphthoyl)indole
• CAS No.: 209414-07-3
• Molecular Formula: C₂₄H₂₃NO
• Molecular Weight: 341.453
• European Community (EC) Number: 635-711-0
• UNII: G391998J57
• DSSTox Substance ID: DTXSID10175117
• Nikkaji Number: J770.893I
• Wikipedia: JWH-018
• Wikidata: Q419020
• Pharos Ligand ID: VKFTDZGUTJKU
• ChEMBL ID: CHEMBL561013
• Mol file: 209414-07-3.mol

Synonyms:1-pentyl-3-(1-naphthoyl)indole;JWH 018;JWH-018;JWH018;naphthalen-1-yl-(1-pentylindol-3-yl)methanone

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Chemical Property of 1-Pentyl-3-(1-naphthoyl)indole

Chemical Property:

• Vapor Pressure: 1.73E-11mmHg at 25°C
• Melting Point: 55-59°C
• Boiling Point: 534.2±23.0 °C(Predicted)
• Flash Point: 9℃
• Density: 1.09±0.1 g/cm3(Predicted)
• Storage Temp.: Desiccate at -20°C
• XLogP3: 6.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 6
• Exact Mass: 341.177964357
• Heavy Atom Count: 26
• Complexity: 475

Purity/Quality:

Safty Information:

• Hazard Codes: F,T
• Statements: 11-23/24/25-39/23/24/25-25
• Safety Statements: 7-16-36/37-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCN1C=C(C2=CC=CC=C21)C(=O)C3=CC=CC4=CC=CC=C43
• 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.
• Uses: Analgesic Drug 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.

Technology Process of 1-Pentyl-3-(1-naphthoyl)indole

There total 8 articles about 1-Pentyl-3-(1-naphthoyl)indole which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

1-Bromopentane (110-53-2) + naphthalen-1-yl[1-(phenylsulfonyl)-1H-indol-3-yl]methanone (1226853-98-0) → 1-pentyl-3-(1-naphthoyl)indole (209414-07-3)

Guidance literature:

naphthalen-1-yl[1-(phenylsulfonyl)-1H-indol-3-yl]methanone; With pentan-1-ol; tetrabutylammomium bromide; caesium carbonate; In toluene; for 24h; Reflux; In air;

1-Bromopentane; In toluene; for 8h; Reflux; in air;

DOI:10.1055/S-0029-1218627

Reference yield: 80.0%

1-Bromopentane (110-53-2) + (1H-indol-3-yl)(naphthalene-1-yl)methanone (109555-87-5) → 1-pentyl-3-(1-naphthoyl)indole (209414-07-3)

Guidance literature:

With N,N-dimethyl-formamide; potassium hydroxide; In acetone; at 0 - 40 ℃; for 4h;

DOI:10.1016/j.neuropharm.2017.11.020

Reference yield: 72.0%

1-pentyl-1H-indole (59529-21-4) + naphthalene-1-carbonic acid chloride (879-18-5) → 1-pentyl-3-(1-naphthoyl)indole (209414-07-3)

Guidance literature:

1-pentyl-1H-indole; With diethylaluminium chloride; In hexane; dichloromethane; at 0 ℃; for 1h;

naphthalene-1-carbonic acid chloride; In hexane; dichloromethane; at 0 ℃; for 16h;

DOI:10.1016/j.ejmech.2019.05.037

upstream raw materials:

1-Bromopentane

naphthalen-1-yl[1-(phenylsulfonyl)-1H-indol-3-yl]methanone

indole

naphthalene-1-carbonic acid chloride

Refernces

• 1、 Cooper, Ziva D.,Poklis, Justin L.,Liu, Fei. "Methodology for controlled administration of smoked synthetic cannabinoids JWH-018 and JWH-073". . p. 92 - 100. Retrieved 2017/11/28.
• 2、 Lai, Qiu Yu,Liao, Rong Su,Wu, Shao Yong,Zhang, Jia Xin,Duan, Xin Hong. "A novel microwave-irradiated solvent-free 3-acylation of indoles on alumina". . p. 4069 - 4076. Retrieved 2013/12/04.