Cannabis Ruderalis

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{{Short description|Chemical compound}}
⚫
{{Drugbox
{{About|the drug|the Space Shuttle mission|STS-135}}
⚫
{{Drugbox
| drug_name = STS-135
| drug_name = STS-135
| Verifiedfields =
| Verifiedfields =
| verifiedrevid =
| verifiedrevid =
| 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
| image = STS-135 structure.png
| image = 5F-APICA.svg
| width = 200
| width = 200


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


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| CAS_number_Ref =
| CAS_number_Ref =
| CAS_number = 1354631-26-7
| CAS_number = 1354631-26-7
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = E6917946XH
| ATC_prefix =
| ATC_prefix =
| ATC_suffix =
| ATC_suffix =
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<!--Chemical data-->
<!--Chemical data-->
| C=24 | H=31 | F=1 | N=2 | O=1
| C=24 | H=31 | F=1 | N=2 | O=1
| molecular_weight = 382.51 g/mol
}}
}}


'''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 utilise an understanding of [[structure-activity relationship]]s within the indole class of cannabimimetics, although its design origins are unclear.<ref>{{Cite journal | doi = 10.1071/CH14198| title = Bioisosteric Fluorine in the Clandestine Design of Synthetic Cannabinoids| journal = Australian Journal of Chemistry| volume = 68| pages = 4| year = 2015| last1 = Wilkinson | first1 = S. M. | last2 = Banister | first2 = S. D. | last3 = Kassiou | first3 = M. }}</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&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 | doi = 10.1021/acschemneuro.5b00107| 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| pages = 150508124201002| year = 2015| last1 = Banister | first1 = S. D. | last2 = Stuart | first2 = J. | last3 = Kevin | first3 = R. C. | last4 = Edington | first4 = A. | last5 = Longworth | first5 = M. | last6 = Wilkinson | first6 = S. M. | last7 = Beinat | first7 = C. | last8 = Buchanan | first8 = A. S. | last9 = Hibbs | first9 = D. E. | last10 = Glass | first10 = M. | last11 = Connor | first11 = M. | last12 = McGregor | first12 = I. S. | last13 = Kassiou | first13 = M. }}</ref> STS-135 produces bradycardia and hypothermia in rats at doses of 1–10&nbsp;mg/kg, suggesting cannabinoid-like activity.<ref name=ACS />
'''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&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 [[bradycardia]] and hypothermia in rats at doses of 1–10&nbsp;mg/kg, suggesting cannabinoid-like activity.<ref name=ACS />


==Legal Status==
==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 | accessdate=1 October 2015}}</ref>
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==
==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>
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==
== See also ==
* [[AB-001]]
* [[AB-001]]
* [[ADAMANTYL-THPINACA]]
* [[ADAMANTYL-THPINACA]]
* [[APICA]]
* [[APICA (synthetic cannabinoid drug)|APICA]]
* [[APINACA]]
* [[APINACA]]
* [[AM-2201]]
* [[AM-2201]]
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* [[XLR-11 (drug)|XLR-11]]
* [[XLR-11 (drug)|XLR-11]]


==References==
== References ==
{{reflist}}
{{reflist}}


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[[Category:Indoles]]
[[Category:Indoles]]
[[Category:Indolecarboxamides]]
[[Category:Indolecarboxamides]]



{{cannabinoid-stub}}
{{cannabinoid-stub}}

Latest revision as of 00:22, 5 May 2022

This article is about the drug. For the Space Shuttle mission, see STS-135.
STS-135
Legal status
Legal status
Identifiers
  • 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)
  • FCCCCCn1cc(c2c1cccc2)C(=O)NC12CC3CC(C2)CC(C1)C3
  • 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]

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]

  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. ^ 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.
  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
source: https://en.wikipedia.org/w/index.php?title=STS-135_(drug)&diff=1086238112&oldid=732691428

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