Chemistry:STS-135 (drug)

From HandWiki
Short description: Chemical compound
STS-135
5F-APICA.svg
Legal status
Legal status
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC24H31FN2O
Molar mass382.523 g·mol−1
3D model (JSmol)

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]

Legal status

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. "Bioisosteric Fluorine in the Clandestine Design of Synthetic Cannabinoids". Australian Journal of Chemistry 68: 4. 2015. doi:10.1071/CH14198. 
  2. 2.0 2.1 "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. August 2015. doi:10.1021/acschemneuro.5b00107. PMID 25921407. https://zenodo.org/record/47750. 
  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. http://www.sfda.gov.cn/WS01/CL0056/130753.html. 
  4. Southern Association of Forensic Scientists