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Details

Stereochemistry ACHIRAL
Molecular Formula C20H21FN2O
Molecular Weight 324.3927
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 5F-SDB-005

SMILES

c1ccc(cc1)N=C(c2cn(CCCCCF)c3ccccc23)O

InChI

InChIKey=FZYJALPWLNXEIP-UHFFFAOYSA-N
InChI=1S/C20H21FN2O/c21-13-7-2-8-14-23-15-18(17-11-5-6-12-19(17)23)20(24)22-16-9-3-1-4-10-16/h1,3-6,9-12,15H,2,7-8,13-14H2,(H,22,24)

HIDE SMILES / InChI

Molecular Formula C20H21FN2O
Molecular Weight 324.3927
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment:: The description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/25921407

SDB-006 is a cannabimimetic indole that binds the central cannabinoid (CB1) and peripheral cannabinoid (CB2) receptors with EC50 values of 19 and 134 nM, respectively. SDB-006 was discovered during research of the related compound JWH-018 adamantyl carboxamide, which has been sold illicitly in herbal blends.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
6.88 null [pEC50]
6.94 null [pEC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Effects of bioisosteric fluorine in synthetic cannabinoid designer drugs JWH-018, AM-2201, UR-144, XLR-11, PB-22, 5F-PB-22, APICA, and STS-135.
2015 Aug 19

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
Mouse AtT20 neuroblastoma cells stably transfected with human CB1 or human CB2 were used for activity evaluation. Membrane potential was measured using a FLIPR Membrane Potential Assay kit (blue) from Molecular Devices. The dye was reconstituted with assay buffer of composition (mM): NaCl 145, HEPES 22, Na2HPO4 0.338, NaHCO3 4.17, KH2PO4 0.441, MgSO4 0.407, MgCl2 0.493, CaCl2 1.26, glucose 5.56 (pH 7.4, osmolarity 315 ± 5). Prior to the assay, cells were loaded with 90 μL/well of the dye solution without removal of the L-15, giving an initial assay volume of 180 μL/well. Plates were then incubated at 37 °C at ambient CO2 for 45 min. Fluorescence was measured using a FlexStation 3 (Molecular Devices) microplate reader with cells excited at a wavelength of 530 nm and emission measured at 565 nm. Baseline readings were taken every 2 s for at least 2 min, at which time either drug (SDB-006) or vehicle was added in a volume of 20 μL. The background fluorescence of cells without dye or dye without cells was negligible. Changes in fluorescence were expressed as a percentage of baseline fluorescence after subtraction of the changes produced by vehicle addition, which was less than 2% for drugs dissolved in assay buffer or DMSO. The final concentration of DMSO was not more than 0.1%.
Substance Class Chemical
Created
by admin
on Sat Jun 26 13:00:44 UTC 2021
Edited
by admin
on Sat Jun 26 13:00:44 UTC 2021
Record UNII
3X4PHX3PGF
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
5F-SDB-005
Common Name English
N-PHENYL-1-(5-FLUOROPENTYL)-1H-INDOLE-3-CARBOXAMIDE
Systematic Name English
1H-INDOLE-3-CARBOXAMIDE, 1-(5-FLUOROPENTYL)-N-PHENYL-
Systematic Name English
Code System Code Type Description
PUBCHEM
91936840
Created by admin on Sat Jun 26 13:00:45 UTC 2021 , Edited by admin on Sat Jun 26 13:00:45 UTC 2021
PRIMARY
CAS
1776086-01-1
Created by admin on Sat Jun 26 13:00:45 UTC 2021 , Edited by admin on Sat Jun 26 13:00:45 UTC 2021
PRIMARY
FDA UNII
3X4PHX3PGF
Created by admin on Sat Jun 26 13:00:45 UTC 2021 , Edited by admin on Sat Jun 26 13:00:45 UTC 2021
PRIMARY
Related Record Type Details
TARGET -> AGONIST
Mouse AtT-20 neuroblastoma cells stably transfected with human CB2
EC50
TARGET -> AGONIST
Mouse AtT-20 neuroblastoma cells stably transfected with human CB1
EC50
Related Record Type Details
ACTIVE MOIETY