View source for Chemistry:STS-135 (drug)

{{Short description|Chemical compound}}
{{Drugbox 
| drug_name = STS-135
| Verifiedfields = 
| verifiedrevid = 
| IUPAC_name = ''N''-(Adamantan-1-yl)-1-(5-fluoropentyl)-1''H''-indole-3-carboxamide
| image = 5F-APICA.svg
| width = 200

<!--Clinical data-->
| tradename =  
| pregnancy_AU = <!-- A, B1, B2, B3, C, D, X -->
| pregnancy_US = <!-- A, B, C, D, X -->
| pregnancy_category =  
| legal_AU = <!-- Unscheduled, S2, S3, S4, S5, S6, S7, S8, S9 -->
| legal_CA = Schedule II
| legal_UK = Class B
| legal_US = <!-- OTC, Rx-only, Schedule I, II, III, IV, V -->
| legal_DE = Anlage II
| legal_NZ = Temporary class
| routes_of_administration =

<!--Pharmacokinetic data-->
| bioavailability =  
| protein_bound =  
| metabolism =  
| elimination_half-life =  
| excretion =

<!--Identifiers-->
| CAS_number_Ref =
| CAS_number = 1354631-26-7 
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = E6917946XH
| ATC_prefix =  
| ATC_suffix =  
| PubChem = 57404059
| DrugBank_Ref =
| DrugBank =  
|  ChemSpiderID_Ref = 
| ChemSpiderID = 28189067
| smiles            = FCCCCCn1cc(c2c1cccc2)C(=O)NC12CC3CC(C2)CC(C1)C3
| StdInChI          = 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)
| StdInChIKey       =  	COYHGVCHRRXECF-UHFFFAOYSA-N

<!--Chemical data-->
| C=24 | H=31 | F=1 | N=2 | O=1 
}}

'''STS-135''' ('''''N''-(adamantan-1-yl)-1-(5-fluoropentyl)-1''H''-indole-3-carboxamide''', also called '''5F-APICA''') is a [[Chemistry:Designer drug|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.<ref>{{Cite journal | vauthors = Wilkinson SM, Banister SD, Kassiou M | title = Bioisosteric Fluorine in the Clandestine Design of Synthetic Cannabinoids| journal = Australian Journal of Chemistry| volume = 68| pages = 4| year = 2015 | doi = 10.1071/CH14198 }}</ref> STS-135 is the terminally-fluorinated analogue of SDB-001, just as [[Chemistry:AM-2201|AM-2201]] is the terminally-fluorinated analogue of [[Chemistry:JWH-018|JWH-018]], and XLR-11 is the terminally-fluorinated analogue of [[Chemistry:UR-144|UR-144]]. STS-135 acts a potent cannabinoid receptor agonist in vitro, with an [[Chemistry:EC50|EC<sub>50</sub>]] of 51&nbsp;nM for human CB<sub>2</sub> receptors, and 13&nbsp;nM for human CB<sub>1</sub> receptors.<ref name=ACS>{{cite journal | vauthors = Banister SD, Stuart J, Kevin RC, Edington A, Longworth M, Wilkinson SM, Beinat C, Buchanan AS, Hibbs DE, Glass M, Connor M, McGregor IS, Kassiou M | display-authors = 6 | title = 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 | journal = ACS Chemical Neuroscience | volume = 6 | issue = 8 | pages = 1445–58 | date = August 2015 | pmid = 25921407 | doi = 10.1021/acschemneuro.5b00107 | url = https://zenodo.org/record/47750 }}</ref> STS-135 produces [[Medicine:Bradycardia|bradycardia]] and hypothermia in rats at doses of 1–10&nbsp;mg/kg, suggesting cannabinoid-like activity.<ref name=ACS />

==Legal status==

As of October 2015 STS-135 is a controlled substance in China.<ref>{{cite web | url=http://www.sfda.gov.cn/WS01/CL0056/130753.html | title=关于印发《非药用类麻醉药品和精神药品列管办法》的通知 | publisher=China Food and Drug Administration | date=27 September 2015 | language=Chinese | access-date=1 October 2015}}</ref> 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.<ref>[http://forendex.southernforensic.org/index.php/detail/index/1217 Southern Association of Forensic Scientists]</ref>

== See also ==
* [[Chemistry:AB-001|AB-001]]
* ADAMANTYL-THPINACA
* [[Chemistry:APICA (synthetic cannabinoid drug)|APICA]]
* [[Chemistry:APINACA|APINACA]]
* [[Chemistry:AM-2201|AM-2201]]
* [[Chemistry:JWH-018|JWH-018]]
* [[Chemistry:UR-144|UR-144]]
* XLR-11

== References ==
{{reflist}}

{{Cannabinoids}}

[[Category:Adamantanes]]
[[Category:Cannabinoids]]
[[Category:Designer drugs]]
[[Category:Organofluorides]]
[[Category:Indoles]]


{{Sourceattribution|STS-135 (drug)}}