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{{Short description|Chemical compound}} |
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{{About|the drug|the Space Shuttle mission|STS-135}} |
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| drug_name = STS-135 |
| drug_name = STS-135 |
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| Verifiedfields = |
| Verifiedfields = |
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| verifiedrevid = |
| verifiedrevid = |
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| IUPAC_name = ''N''-(Adamantan-1-yl)-1-(5-fluoropentyl)-1''H''-indole-3-carboxamide |
| IUPAC_name = ''N''-(Adamantan-1-yl)-1-(5-fluoropentyl)-1''H''-indole-3-carboxamide |
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| image = |
| image = 5F-APICA.svg |
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| width = 200 |
| width = 200 |
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<!--Clinical data--> |
<!--Clinical data--> |
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| tradename = |
| tradename = |
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| pregnancy_AU = <!-- A |
| pregnancy_AU = <!-- A, B1, B2, B3, C, D, X --> |
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| pregnancy_US = <!-- A |
| pregnancy_US = <!-- A, B, C, D, X --> |
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| pregnancy_category = |
| pregnancy_category = |
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| legal_AU = <!-- Unscheduled |
| legal_AU = <!-- Unscheduled, S2, S3, S4, S5, S6, S7, S8, S9 --> |
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| legal_CA = |
| legal_CA = Schedule II |
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| legal_UK = |
| legal_UK = Class B |
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| legal_US = <!-- OTC |
| legal_US = <!-- OTC, Rx-only, Schedule I, II, III, IV, V --> |
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| legal_DE = Anlage II |
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| |
| legal_NZ = Temporary class |
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| routes_of_administration = |
| routes_of_administration = |
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<!--Pharmacokinetic data--> |
<!--Pharmacokinetic data--> |
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| metabolism = |
| metabolism = |
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| elimination_half-life = |
| elimination_half-life = |
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| excretion = |
| excretion = |
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<!--Identifiers--> |
<!--Identifiers--> |
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| CAS_number_Ref = |
| CAS_number_Ref = |
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| CAS_number = 1354631-26-7 |
| CAS_number = 1354631-26-7 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = E6917946XH |
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| ATC_prefix = |
| ATC_prefix = |
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| ATC_suffix = |
| ATC_suffix = |
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| PubChem = |
| PubChem = 57404059 |
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| DrugBank_Ref = |
| DrugBank_Ref = |
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| DrugBank = |
| DrugBank = |
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| ChemSpiderID_Ref = |
| ChemSpiderID_Ref = |
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| ChemSpiderID = |
| ChemSpiderID = 28189067 |
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| smiles = FCCCCCn1cc(c2c1cccc2)C(=O)NC12CC3CC(C2)CC(C1)C3 |
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| smiles = |
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| 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) |
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| StdInChIKey = COYHGVCHRRXECF-UHFFFAOYSA-N |
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<!--Chemical data--> |
<!--Chemical data--> |
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| C=24 | H=31 | F=1 | N=2 | O=1 |
| C=24 | H=31 | F=1 | N=2 | O=1 |
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| molecular_weight = 382.51 g/mol |
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}} |
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'''STS-135''' ('''''N''-(adamantan-1-yl)-1-(5-fluoropentyl)-1''H''-indole-3-carboxamide''') is a [[designer drug]] offered by online vendors as a cannabimimetic agent. The structure of STS-135 appears to |
'''STS-135''' ('''''N''-(adamantan-1-yl)-1-(5-fluoropentyl)-1''H''-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 relationship]]s 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 [[AM-2201]] is the terminally-fluorinated analogue of [[JWH-018]], and [[XLR-11 (drug)|XLR-11]] is the terminally-fluorinated analogue of [[UR-144]]. STS-135 acts a potent cannabinoid receptor agonist in vitro, with an [[EC50|EC<sub>50</sub>]] of 51 nM for human CB<sub>2</sub> receptors, and 13 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 [[bradycardia]] and hypothermia in rats at doses of 1–10 mg/kg, suggesting cannabinoid-like activity.<ref name=ACS /> |
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==Legal status== |
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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. |
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==Detection== |
==Detection== |
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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> |
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> |
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==See also== |
== See also == |
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* [[AB-001]] |
* [[AB-001]] |
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* [[ADAMANTYL-THPINACA]] |
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* [[APICA (synthetic cannabinoid drug)|APICA]] |
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* [[APINACA]] |
* [[APINACA]] |
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* [[AM-2201]] |
* [[AM-2201]] |
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* [[JWH-018]] |
* [[JWH-018]] |
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* [[ |
* [[UR-144]] |
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* [[XLR-11 (drug)|XLR-11]] |
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==References== |
== References == |
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{{reflist}} |
{{reflist}} |
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{{Cannabinoids}} |
{{Cannabinoids}} |
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[[Category:Adamantanes]] |
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[[Category:Cannabinoids]] |
[[Category:Cannabinoids]] |
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[[Category:Designer drugs]] |
[[Category:Designer drugs]] |
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[[Category: |
[[Category:Organofluorides]] |
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[[Category:Indoles]] |
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[[Category:Indolecarboxamides]] |
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{{cannabinoid-stub}} |
{{cannabinoid-stub}} |
Latest revision as of 00:22, 5 May 2022
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Chemical and physical data | |
Formula | C24H31FN2O |
Molar mass | 382.523 g·mol−1 |
3D model (JSmol) | |
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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[edit]
As of October 2015 STS-135 is a controlled substance in China.[3] It is also illegal in the UK.
Detection[edit]
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[edit]
References[edit]
- ^ 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.
- ^ a b 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.
- ^ "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.
- ^ Southern Association of Forensic Scientists