5F-SDB-006

5F-SDB-006
Legal status
Legal status	CA: Schedule II ; DE: Anlage II (Authorized trade only, not prescriptible) ;
Identifiers
	IUPAC name N-benzyl-1-(5-fluoropentyl)-1H-indole-3-carboxamide;
CAS Number	1776086-02-2;
PubChem CID	91936847;
ChemSpider	30646773;
UNII	4UP4SXX8BW;
Chemical and physical data
Formula	C21H23FN2O
Molar mass	338.43 g/mol
3D model (JSmol)	Interactive image;
	SMILES FCCCCCN1C=C(C(NCC2=CC=CC=C2)=O)C3=C1C=CC=C3;
	InChI 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.

References

↑ Banister, S. D.; Stuart, J.; Kevin, R. C.; Edington, A.; Longworth, M.; Wilkinson, S. M.; Beinat, C.; Buchanan, A. S.; Hibbs, D. E.; Glass, M.; Connor, M.; McGregor, I. S.; Kassiou, M. (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): 1445–1458. doi:10.1021/acschemneuro.5b00107. PMID 25921407.
↑ Banister, S. D.; Wilkinson, S. M.; Longworth, M.; Stuart, J.; Apetz, N.; English, K.; Brooker, L.; Goebel, C.; Hibbs, D. E.; Glass, M.; Connor, M.; McGregor, I. S.; Kassiou, M. (July 2013). "The synthesis and pharmacological evaluation of adamantane-derived indoles: Novel cannabimimetic drugs of abuse". ACS Chemical Neuroscience. 4 (7): 1081–1092. doi:10.1021/cn400035r. PMC 3715837. PMID 23551277.

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[1] Banister, S. D.; Stuart, J.; Kevin, R. C.; Edington, A.; Longworth, M.; Wilkinson, S. M.; Beinat, C.; Buchanan, A. S.; Hibbs, D. E.; Glass, M.; Connor, M.; McGregor, I. S.; Kassiou, M. (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): 1445–1458. doi:10.1021/acschemneuro.5b00107. PMID 25921407.

[2] Banister, S. D.; Wilkinson, S. M.; Longworth, M.; Stuart, J.; Apetz, N.; English, K.; Brooker, L.; Goebel, C.; Hibbs, D. E.; Glass, M.; Connor, M.; McGregor, I. S.; Kassiou, M. (July 2013). "The synthesis and pharmacological evaluation of adamantane-derived indoles: Novel cannabimimetic drugs of abuse". ACS Chemical Neuroscience. 4 (7): 1081–1092. doi:10.1021/cn400035r. PMC 3715837. PMID 23551277.

Legal status

Legal status	CA: Schedule II DE: Anlage II (Authorized trade only, not prescriptible)
Identifiers
IUPAC name N-benzyl-1-(5-fluoropentyl)-1H-indole-3-carboxamide
CAS Number	1776086-02-2
PubChem CID	91936847
ChemSpider	30646773
UNII	4UP4SXX8BW
Chemical and physical data
Formula	C₂₁H₂₃FN₂O
Molar mass	338.43 g/mol
3D model (JSmol)	Interactive image
SMILES FCCCCCN1C=C(C(NCC2=CC=CC=C2)=O)C3=C1C=CC=C3
InChI 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

See also

References