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Chemical compound
5F-SDB-006
Legal status
N -benzyl-1-(5-fluoropentyl)-1H -indole-3-carboxamide
CAS Number
PubChem
CID
ChemSpider
UNII
Formula C 21 H 23 F N 2 O
Molar mass 338.426 g·mol−1 3D model (
JSmol )
FCCCCCN1C=C(C(NCC2=CC=CC=C2)=O)C3=C1C=CC=C3
InChI=1S/C21H23FN2O/c22-13-7-2-8-14-24-16-19(18-11-5-6-12-20(18)24)21(25)23-15-17-9-3-1-4-10-17/h1,3-6,9-12,16H,2,7-8,13-15H2,(H,23,25)
Key:VFLXAWVAWXHMFB-UHFFFAOYSA-N
5F-SDB-006 is a drug that acts as a potent
agonist for the
cannabinoid receptors , with an EC50 of 50 nM for human CB1 receptors, and 123 nM for human CB2 receptors.
[1] It was discovered during research into the related compound
APICA which had been sold illicitly as "2NE1".
[2] 5F-SDB-006 is the terminally fluorinated analog of
SDB-006 , just as
STS-135 is the terminally fluorinated analog of
APICA . Given the known metabolic liberation (and presence as an impurity) of
amantadine in the related compound
APINACA , it is suspected that metabolic
hydrolysis of the amide group of 5F-SDB-006 may release
benzylamine .
See also
References
^ Banister SD, Stuart J, Kevin RC, Edington A, Longworth M, Wilkinson SM, et al. (August 2015).
"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" . ACS Chemical Neuroscience . 6 (8): 1445–58.
doi :
10.1021/acschemneuro.5b00107 .
PMID
25921407 .
^ Banister SD, Wilkinson SM, Longworth M, Stuart J, Apetz N, English K, et al. (July 2013).
"The synthesis and pharmacological evaluation of adamantane-derived indoles: cannabimimetic drugs of abuse" . ACS Chemical Neuroscience . 4 (7): 1081–92.
doi :
10.1021/cn400035r .
PMC
3715837 .
PMID
23551277 .
Phytocannabinoids (
comparison )
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Allosteric
CBR Tooltip Cannabinoid receptor
ligands
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Anticannabinoids (antagonists/inverse agonists/antibodies)