(1-(2-Morpholin-4-ylethyl)indol-3-yl)-4-methylnaphthalen-1-ylmethanone

Base Information

• Chemical Name: (1-(2-Morpholin-4-ylethyl)indol-3-yl)-4-methylnaphthalen-1-ylmethanone
• CAS No.: 133438-58-1
• Molecular Formula: C₂₆H₂₆N₂O₂
• Molecular Weight: 398.505
• UNII: WB1TIJ1IO9
• DSSTox Substance ID: DTXSID70158108
• Wikipedia: JWH-193
• Wikidata: Q6109209
• Pharos Ligand ID: XY4XU23FCCF3
• ChEMBL ID: CHEMBL80214

Synonyms:JWH-193;133438-58-1;JWH 193;UNII-WB1TIJ1IO9;WB1TIJ1IO9;(1-(2-Morpholin-4-ylethyl)indol-3-yl)-4-methylnaphthalen-1-ylmethanone;CHEMBL80214;(4-methylnaphthalen-1-yl)-[1-(2-morpholin-4-ylethyl)indol-3-yl]methanone;(4-methylnaphthalen-1-yl)(1-(2-morpholinoethyl)-1H-indol-3-yl)methanone;(4-methyl-1-naphthalenyl)[1-[2-(4-morpholinyl)ethyl]-1H-indol-3-yl]-methanone;METHANONE, (4-METHYL-1-NAPHTHALENYL)(1-(2-(4-MORPHOLINYL)ETHYL)-1H-INDOL-3-YL)-;Methanone, (4-methyl-1-naphthalenyl)[1-[2-(4-morpholinyl)ethyl]-1h-indol-3-yl]-;JWH193;SCHEMBL16922129;DTXSID70158108;CHEBI:184072;ICKWPPYMDARCKJ-UHFFFAOYSA-N;BDBM50032565;AKOS040745919;Q6109209;(4-Methyl-naphthalen-1-yl)-[1-(2-morpholin-4-yl-ethyl)-1H-indol-3-yl]-methanone

Chemical Property of (1-(2-Morpholin-4-ylethyl)indol-3-yl)-4-methylnaphthalen-1-ylmethanone

Chemical Property:

• PSA: 34.47000
• LogP: 4.60400
• XLogP3: 4.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 398.199428076
• Heavy Atom Count: 30
• Complexity: 590

Purity/Quality:

99% ^*data from raw suppliers

JWH193 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=C(C2=CC=CC=C12)C(=O)C3=CN(C4=CC=CC=C43)CCN5CCOCC5
• Description: JWH 193 is a synthetic cannabinoid (CB) which binds the central CB1 receptor with high affinity (Ki = 6 nM). This aminoalkylindole shares structural features with the antinociceptive CB1 agonists pravadoline and WIN 55,212-2. The physiological and toxicological properties of Methanone, (4-methyl-1-naphthalenyl)[1-[2-(4-morpholinyl)ethyl]-1H-indol-3-yl]- have not been investigated. This product is intended for research and forensic applications.
• Uses: JWH 193, is a synthetic cannabinoid (CB) which binds the central CB1 receptor with high affinity (Ki = 6 nM). Synthetic Cannabinoids

Technology Process of (1-(2-Morpholin-4-ylethyl)indol-3-yl)-4-methylnaphthalen-1-ylmethanone

There total 2 articles about (1-(2-Morpholin-4-ylethyl)indol-3-yl)-4-methylnaphthalen-1-ylmethanone 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:

4-methyl-1-naphthalenecarbonyl chloride (87700-67-2) + 1-<2-(4-morpholinyl)ethyl>-1H-indole (72395-48-3) → 3-(4-methylnaphthalene-1-carbonyl)-1-[2-(morpholin-4-yl)ethyl]-1H-indole (133438-58-1)

Guidance literature:

With ethylaluminum dichloride; In dichloromethane; toluene; at -78 - 20 ℃; Yield given;

DOI:10.1021/jm00016a013

Reference yield:

4-Methyl-1-naphthoic acid (4488-40-8) → 3-(4-methylnaphthalene-1-carbonyl)-1-[2-(morpholin-4-yl)ethyl]-1H-indole (133438-58-1)

Guidance literature:

Multi-step reaction with 2 steps

1: oxalyl chloride / CH₂Cl₂ / Heating

2: 0.37 g / Et₂AlCl / CH₂Cl₂; hexane / 2 h / 20 °C

With oxalyl dichloride; diethylaluminium chloride; In hexane; dichloromethane; 2: Friedel-Crafts acylation;

DOI:10.1016/S0968-0896(02)00451-0

upstream raw materials:

4-methyl-1-naphthalenecarbonyl chloride

1-<2-(4-morpholinyl)ethyl>-1H-indole

4-Methyl-1-naphthoic acid

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