STS-135 (drug)

STS-135

Legal status
Legal status	CA: Schedule II DE: Anlage II (Prohibited) Temporary class drug (NZ)
Identifiers
IUPAC name N-(Adamantan-1-yl)-1-(5-fluoropentyl)-1H-indole-3-carboxamide
CAS Number	1354631-26-7
PubChem (CID)	57404059
ChemSpider	28189067
Chemical and physical data
Formula	C24H31FN2O
Molar mass	382.51 g/mol
3D model (Jmol)	Interactive image
SMILES FCCCCCn1cc(c2c1cccc2)C(=O)NC12CC3CC(C2)CC(C1)C3
InChI InChI=1S/C24H31FN2O/c25-8-4-1-5-9-27-16-21(20-6-2-3-7-22(20)27)23(28)26-24-13-17-10-18(14-24)12-19(11-17)15-24/h2-3,6-7,16-19H,1,4-5,8-15H2,(H,26,28) Key:COYHGVCHRRXECF-UHFFFAOYSA-N

STS-135 (N-(adamantan-1-yl)-1-(5-fluoropentyl)-1H-indole-3-carboxamide, also called 5F-APICA) is a designer drug offered by online vendors as a cannabimimetic agent. The structure of STS-135 appears to utilise an understanding of structure-activity relationships within the indole class of cannabimimetics, although its design origins are unclear.^[1] STS-135 is the terminally-fluorinated analogue of SDB-001, just as AM-2201 is the terminally-fluorinated analogue of JWH-018, and XLR-11 is the terminally-fluorinated analogue of UR-144. STS-135 acts a potent cannabinoid receptor agonist in vitro, with an EC₅₀ of 51 nM for human CB₂ receptors, and 13 nM for human CB₁ receptors.^[2] STS-135 produces bradycardia and hypothermia in rats at doses of 1–10 mg/kg, suggesting cannabinoid-like activity.^[2]

Legal Status

As of October 2015 STS-135 is a controlled substance in China.^[3]

Detection

A forensic standard of STS-135 is available, and the compound has been posted on the Forendex website of potential drugs of abuse.^[4]

See also

• AB-001
• ADAMANTYL-THPINACA
• APICA
• APINACA
• AM-2201
• JWH-018
• UR-144
• XLR-11

References

1. Wilkinson, S. M.; Banister, S. D.; Kassiou, M. (2015). "Bioisosteric Fluorine in the Clandestine Design of Synthetic Cannabinoids". Australian Journal of Chemistry. 68: 4. doi:10.1071/CH14198.
2. 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. (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: 150508124201002. doi:10.1021/acschemneuro.5b00107.
3. "关于印发《非药用类麻醉药品和精神药品列管办法》的通知" (in Chinese). China Food and Drug Administration. 27 September 2015. Retrieved 1 October 2015.
4. Southern Association of Forensic Scientists