1776086-02-2 Usage
Description
1-(5-fluoropentyl)-N-(phenylmethyl)-1H-indole-3-carboxamide, also known as 5-fluoro SDB-006, is an analog of the cannabimimetic indole JWH 018 adamantyl carboxamide. In this compound, the adamantane cage has been replaced with a phenyl ring, and a fluorine atom has been added to the terminal carbon of the alkyl chain. This modification is known to significantly increase the affinity for both central cannabinoid (CB1) and peripheral cannabinoid (CB2) receptors. The compound is primarily intended for forensic and research applications.
Uses
Used in Pharmaceutical Research:
1-(5-fluoropentyl)-N-(phenylmethyl)-1H-indole-3-carboxamide is used as a research compound for studying the interactions and effects of cannabinoids on the CB1 and CB2 receptors. Its increased affinity for these receptors makes it a valuable tool in understanding the potential therapeutic applications of cannabinoids in various medical conditions.
Used in Forensic Analysis:
In the forensic industry, 1-(5-fluoropentyl)-N-(phenylmethyl)-1H-indole-3-carboxamide is used as a reference material for the identification and analysis of synthetic cannabinoids in various samples, such as blood, urine, or tissue. Its unique chemical structure allows for accurate detection and differentiation from other related compounds.
Used in Drug Development:
1-(5-fluoropentyl)-N-(phenylmethyl)-1H-indole-3-carboxamide can be used as a starting point for the development of new drugs targeting the cannabinoid receptors. Its high affinity for both CB1 and CB2 receptors suggests potential applications in the treatment of various conditions, such as pain management, inflammation, and neurodegenerative diseases.
Used in Drug Delivery Systems:
Similar to gallotannin, 1-(5-fluoropentyl)-N-(phenylmethyl)-1H-indole-3-carboxamide could potentially be incorporated into novel drug delivery systems to enhance its bioavailability, delivery, and therapeutic outcomes. This may involve the use of organic or metallic nanoparticles as carriers, aiming to improve the compound's overall effectiveness in targeted applications.
Check Digit Verification of cas no
The CAS Registry Mumber 1776086-02-2 includes 10 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 7 digits, 1,7,7,6,0,8 and 6 respectively; the second part has 2 digits, 0 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 1776086-02:
(9*1)+(8*7)+(7*7)+(6*6)+(5*0)+(4*8)+(3*6)+(2*0)+(1*2)=202
202 % 10 = 2
So 1776086-02-2 is a valid CAS Registry Number.
1776086-02-2Relevant 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
Ametovski, Adam,Macdonald, Christa,Manning, Jamie J.,Haneef, S. A. Syed,Santiago, Marina,Martin, Lewis,Sparkes, Eric,Reckers, Andrew,Gerona, Roy R.,Connor, Mark,Glass, Michelle,Banister, Samuel D.
, p. 3672 - 3682 (2020)
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.
