Trends in LIMS

STS-135

Legal status
Legal status	CA: Schedule II DE: Anlage II (Authorized trade only, not prescriptible) NZ: Temporary Class UK: Class B
Identifiers
IUPAC name N-(Adamantan-1-yl)-1-(5-fluoropentyl)-1H-indole-3-carboxamide
CAS Number	1354631-26-7
PubChem CID	57404059
ChemSpider	28189067
UNII	E6917946XH
CompTox Dashboard (EPA)	DTXSID40725427
Chemical and physical data
Formula	C24H31FN2O
Molar mass	382.523 g·mol−1
3D model (JSmol)	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 use 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]

As of October 2015 STS-135 is a controlled substance in China.^[3] It is also illegal in the UK.

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

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