1400742-32-6

Basic information

• Product Name: N-(1-methyl-1-phenylethyl)-1-pentyl-1H-indole-3-carboxamide
• CAS NO: 1400742-32-6
• Molecular Weight: 348.488
• Mol File: 1400742-32-6.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: N-(1-methyl-1-phenylethyl)-1-pentyl-1H-indole-3-carboxamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-(1-methyl-1-phenylethyl)-1-pentyl-1H-indole-3-carboxamide(1400742-32-6)
• EPA Substance Registry System: N-(1-methyl-1-phenylethyl)-1-pentyl-1H-indole-3-carboxamide(1400742-32-6)

Safety Data

• Hazardous Substances Data: 1400742-32-6(Hazardous Substances Data)

Upstream product

• 59529-21-4 1-pentyl-1H-indole 
• 1338925-23-7 1-pentyl-1H-indole-3-carbonyl chloride 
• 585-32-0 2-phenyl-2-propylamine 
• 727421-73-0 1-pentyl-1H-indole-3-carboxylic acid 
• 1430634-90-4 N-pentyl-3-trifluoroacetylindole 
• 110-53-2 1-Bromopentane 
• 120-72-9 indole 

Relevant articles and documents

Exploring Stereochemical and Conformational Requirements at Cannabinoid Receptors for Synthetic Cannabinoids Related to SDB-006, 5F-SDB-006, CUMYL-PICA, and 5F-CUMYL-PICA

Synthetic cannabinoid receptor agonists (SCRAs) represent the most rapidly expanding class of new psychoactive substances (NPSs). Despite the prevalence and potency of recent chiral indole-3-carboxamide SCRAs, few pharmacological data are available regarding the enantiomeric bias of these NPSs toward human CB1 and CB2 receptors. A series of homochiral indole-3-carboxamides derived from (S)- and (R)-α-methylbenzylamine and featuring variation of the 1-alkyl substituent were prepared, pharmacologically evaluated, and compared to related achiral congeners derived from cumyl- and benzylamine. Competitive binding assays demonstrated that all analogues derived from either enantiomer of α-methylbenzylamine (14-17) showed affinities for CB1 (Ki = 47.9-813 nM) and CB2 (Ki = 47.9-347 nM) that were intermediate to that of the corresponding benzylic (10-13, CB1 Ki = 550 nM to >10 μM; CB2 Ki = 61.7 nM to >10 μM) and cumyl derivatives (6-9, CB1 Ki = 12.6-21.4 nM; CB2 Ki = 2.95-24.5 nM). In a fluorometric membrane potential assay, all α-methylbenzyl analogues (excluding 17) were potent, efficacious agonists of CB1 (EC50 = 32-464 nM; Emax = 89-104%) and low efficacy agonists of CB2 (EC50 = 54-500 nM; Emax = 52-77%), with comparable or greater potency than the benzyl analogues and much lower potency than the cumyl derivatives, consistent with binding trends. The relatively greater affinity and potency of (S)-14-17 compared to (R)-14-17 analogues at CB1 highlighted an enantiomeric bias for this series of SCRAs. Molecular dynamics simulations provided a conformational basis for the observed differences in agonist potency at CB1 pending benzylic substitution.