1338925-11-3

Basic information

• Product Name: 1-pentyl-N-(naphthalen-1-yl)-1H-indole-3-carboxaMide
• Synonyms: 1-pentyl-N-(naphthalen-1-yl)-1H-indole-3-carboxaMide;MN-24;NNEI;N-1-Naphthalenyl-1-pentyl-1H-indole-3-carboxamide;N-(Naphthalen-1-yl)-1-pentyl-1H-indole-3-carboxamide;MN-24 ada@tuskwei.com sky
• CAS NO: 1338925-11-3
• Molecular Formula: C₂₄H₂₄N₂O
• Molecular Weight: 356.46016
• EINECS: -0
• Product Categories: Food additives;research chemical;MN-24 ada@tuskwei.com sky;18031153937@189.cn
• Mol File: 1338925-11-3.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• Density: 1.12±0.1 g/cm3 (20 oC 760 Torr), Calc.*
• CAS DataBase Reference: 1-pentyl-N-(naphthalen-1-yl)-1H-indole-3-carboxaMide(CAS DataBase Reference)
• NIST Chemistry Reference: 1-pentyl-N-(naphthalen-1-yl)-1H-indole-3-carboxaMide(1338925-11-3)
• EPA Substance Registry System: 1-pentyl-N-(naphthalen-1-yl)-1H-indole-3-carboxaMide(1338925-11-3)

Safety Data

• Hazardous Substances Data: 1338925-11-3(Hazardous Substances Data)

Usage

Description

JWH 018 is a potent synthetic cannabinoid which has been identified in smoking mixtures. NNEI is an analog of JWH 018 which differs by having an amide linker inserted between the naphthalene and ketone groups. The physiological and toxicological properties of this compound are not known. This product is intended for forensic and research applications.

Uses

Different sources of media describe the Uses of 1338925-11-3 differently. You can refer to the following data:
1. N-1-Naphthalenyl-1-pentyl-1H-indole-3-carboxamide is a novel indole and azaindole cannabinoid receptor agonists.
2. N-1-Naphthalenyl-1-pentyl-1H-indole-3-carboxamide is a novel indole and azaindole cannabinoid receptor agonists. Synthetic Cannabinoids

Synthetic route

methyl 1-pentyl-1H-indole-3-carboxylate (1338925-20-4) + 1-amino-naphthalene (134-32-7) → N-(naphthalen-1-yl)-1-pentyl-1H-indole-3-carboxamide (1338925-11-3)

Conditions	Yield
Stage #1: 1-amino-naphthalene With trimethylaluminum In 1,2-dichloro-ethane; toluene at 20℃; for 0.166667h; Inert atmosphere; Stage #2: methyl 1-pentyl-1H-indole-3-carboxylate In 1,1,1-trichloroethane; toluene for 24h; Inert atmosphere; Reflux;	85%

3-methoxycarbonylindole (942-24-5) → N-(naphthalen-1-yl)-1-pentyl-1H-indole-3-carboxamide (1338925-11-3)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C / Inert atmosphere 1.2: 16 h / 0 - 20 °C / Inert atmosphere 2.1: trimethylaluminum / 1,2-dichloro-ethane; toluene / 0.17 h / 20 °C / Inert atmosphere 2.2: 24 h / Inert atmosphere; Reflux View Scheme

1-Bromopentane (110-53-2) → N-(naphthalen-1-yl)-1-pentyl-1H-indole-3-carboxamide (1338925-11-3)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C / Inert atmosphere 1.2: 16 h / 0 - 20 °C / Inert atmosphere 2.1: trimethylaluminum / 1,2-dichloro-ethane; toluene / 0.17 h / 20 °C / Inert atmosphere 2.2: 24 h / Inert atmosphere; Reflux View Scheme

Upstream product

• 1338925-20-4 methyl 1-pentyl-1H-indole-3-carboxylate 
• 134-32-7 1-amino-naphthalene 
• 942-24-5 3-methoxycarbonylindole 
• 110-53-2 1-Bromopentane 

Relevant articles and documents

Novel indole and azaindole (pyrrolopyridine) cannabinoid (CB) receptor agonists: Design, synthesis, structure-activity relationships, physicochemical properties and biological activity

The discovery, synthesis and structure-activity relationship (SAR) of a novel series of cannabinoid 1 (CB1) and cannabinoid 2 (CB 2) receptor ligands are reported. Based on the aminoalkylindole class of cannabinoid receptor agonists, a biphenyl moiety was introduced as novel lipophilic indole 3-acyl substituent in 11-16. Furthermore, the 3-carbonyl tether was replaced with a carboxamide linker in 17-20 and the azaindole (pyrrolopyridine) nucleus was designed as indole bioisostere with improved physicochemical properties in 21-25. Through these SAR efforts, several high affinity CB1/CB2 dual cannabinoid receptor ligands were identified. Indole-3-carboxamide 17 displayed single-digit nanomolar affinity and ～80 fold selectivity for CB1 over the CB2 receptor. The azaindoles displayed substantially improved physicochemical properties (lipophilicity; aqueous solubility). Azaindole 21 elicited potent cannabinoid activity. Cannabinoid receptor agonists 17 and 21 potently modulated excitatory synaptic transmission in an acute rat brain slice model of cannabinoid receptor-modulated neurotransmission.