STS-135 (drug)

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
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC24H31FN2O
Molar mass382.523 g·mol−1
3D model (JSmol)
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.

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

References

  1. ↑ Wilkinson SM, Banister SD, Kassiou M (2015). "Bioisosteric Fluorine in the Clandestine Design of Synthetic Cannabinoids". Australian Journal of Chemistry. 68: 4. doi:10.1071/CH14198.
  2. 1 2 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.
  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
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