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5F-SDB-006

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
5F-SDB-006
Legal status
Legal status
Identifiers
  • N-benzyl-1-(5-fluoropentyl)-1H-indole-3-carboxamide
CAS Number
PubChemCID
ChemSpider
UNII
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC21H23FN2O
Molar mass338.426 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 potentagonist for thecannabinoid 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 compoundAPICA which had been sold illicitly as "2NE1".[2] 5F-SDB-006 is the terminally fluorinated analog ofSDB-006, just asSTS-135 is the terminally fluorinated analog ofAPICA. Given the known metabolic liberation (and presence as an impurity) ofamantadine in the related compoundAPINACA, it is suspected that metabolichydrolysis of the amide group of 5F-SDB-006 may releasebenzylamine.

See also

[edit]

References

[edit]
  1. ^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.
  2. ^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.
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