5F-SDB-006

5F-SDB-006
Legal status
Legal status	CA: Schedule II; DE: Anlage II (Authorized trade only, not prescriptible); UK: Class B;
Identifiers
	IUPAC name N-benzyl-1-(5-fluoropentyl)-1H-indole-3-carboxamide;
CAS Number	1776086-02-2;
PubChem CID	91936847;
ChemSpider	30646773;
UNII	4UP4SXX8BW;
CompTox Dashboard (EPA)	DTXSID601032523 ;
Chemical and physical data
Formula	C21H23FN2O
Molar mass	338.426 g·mol−1
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. 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.

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.

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[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.

[1]

[2]

Legal status

Legal status	CA: Schedule II DE: Anlage II (Authorized trade only, not prescriptible) UK: Class B
Identifiers
IUPAC name N-benzyl-1-(5-fluoropentyl)-1H-indole-3-carboxamide
CAS Number	1776086-02-2
PubChem CID	91936847
ChemSpider	30646773
UNII	4UP4SXX8BW
CompTox Dashboard (EPA)	DTXSID601032523
Chemical and physical data
Formula	C₂₁H₂₃FN₂O
Molar mass	338.426 g·mol⁻¹
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