View source for Chemistry:XLR-11

{{Short description|Chemical compound}}
{{Drugbox
| drug_name =
| IUPAC_name = (1-(5-fluoropentyl)-1H-indol-3-yl)(2,2,3,3-tetramethylcyclopropyl)methanone
| image = XLR-11_structure.png

<!--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_BR = F2
| legal_CA = Schedule II
| legal_UK = Class B
| legal_US = Schedule I
| legal_US_comment =
| legal_NZ = Temporary Class
| legal_DE = Anlage II
| routes_of_administration =

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

<!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 1364933-54-9
| ATC_prefix =  
| ATC_suffix =  
| PubChem = 57501498
| KEGG = C22770
| ChemSpiderID      = 28537382
| UNII = L2M8B977ZE
| smiles            = CC1(C(C1(C)C)C(=O)c2cn(c3c2cccc3)CCCCCF)C
| StdInChI          = 1S/C21H28FNO/c1-20(2)19(21(20,3)4)18(24)16-14-23(13-9-5-8-12-22)17-11-7-6-10-15(16)17/h6-7,10-11,14,19H,5,8-9,12-13H2,1-4H3
| StdInChIKey       = PXLDPUUMIHVLEC-UHFFFAOYSA-N

<!--Chemical data-->
| C=21 | H=28 | F=1 | N=1 | O=1 
}}

'''XLR-11''' ('''5"-fluoro-UR-144''' or '''5F-UR-144''') is a drug that acts as a potent [[Biology:Agonist|agonist]] for the [[Biology:Cannabinoid receptor|cannabinoid receptor]]s [[Biology:Cannabinoid receptor type 1|CB<sub>1</sub>]] and [[Biology:Cannabinoid receptor type 2|CB<sub>2</sub>]] with EC<sub>50</sub> values of 98 nM and 83 nM, respectively.<ref name="doi10.1021/acschemneuro.5b00107">{{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 = 1445–1458 | date = August 2015 | pmid = 25921407 | doi = 10.1021/acschemneuro.5b00107 | url = https://zenodo.org/record/47750 }}</ref> It is a 3-(tetramethylcyclopropylmethanoyl)indole derivative related to compounds such as [[Chemistry:UR-144|UR-144]], [[Chemistry:A-796,260|A-796,260]] and [[Chemistry:A-834,735|A-834,735]], but it is not specifically listed in the patent or scientific literature alongside these other similar compounds,<ref name = "WO2006/069196">{{cite patent |country= WO |number= 2006069196 |status= application |title= 3-Cycloalkylcarbonyl indoles as cannabinoid receptor ligands |pubdate= 2006-06-29 |inventor= Pace JM, Tietje K, Dart MJ, Meyer MD |assign1= Abbott Laboratories }}</ref><ref name="pmid19921781">{{cite journal | vauthors = Frost JM, Dart MJ, Tietje KR, Garrison TR, Grayson GK, Daza AV, El-Kouhen OF, Yao BB, Hsieh GC, Pai M, Zhu CZ, Chandran P, Meyer MD | display-authors = 6 | title = Indol-3-ylcycloalkyl ketones: effects of N1 substituted indole side chain variations on CB(2) cannabinoid receptor activity | journal = Journal of Medicinal Chemistry | volume = 53 | issue = 1 | pages = 295–315 | date = January 2010 | pmid = 19921781 | doi = 10.1021/jm901214q }}</ref> and appears to have not previously been made by [[Organization:Abbott Laboratories|Abbott Laboratories]], despite falling within the claims of patent WO 2006/069196. XLR-11 was found to produce rapid, short-lived hypothermic effects in rats at doses of 3&nbsp;mg/kg and 10&nbsp;mg/kg, suggesting that it is of comparable potency to [[Chemistry:APICA (synthetic cannabinoid drug)|APICA]] and [[Chemistry:STS-135 (drug)|STS-135]].<ref name="doi10.1021/acschemneuro.5b00107"/>

==Detection==

A forensic standard for this compound is available, and a representative mass spectrum has been posted on Forendex.<ref name="url__forendex">{{cite web | url = http://forendex.southernforensic.org/index.php/detail/index/1219%20XLR-11 | title =XLR-11 | work = Structural, chemical, and analytical data on controlled substances | publisher = Southern Association of Forensic Scientists (SAFS)  }}</ref>

==Recreational use==
XLR-11 was instead first identified by laboratories in 2012 as an ingredient in synthetic cannabis smoking blends, and appears to be a novel compound invented specifically for grey-market recreational use.<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| vauthors = Wilkinson SM, Banister SD, Kassiou M }}</ref>

==Legal Status==

XLR-11 was banned in New Zealand by being added to the [[Medicine:Temporary class drug|temporary class drug]] schedule, effective from 13 July 2012.<ref name="url_New_Zealand_Gazette">{{cite web | url = http://www.dia.govt.nz/MSOS118/On-Line/NZGazette.nsf/6cee7698a9bbc7cfcc256d510059ed0b/1800482ea20e00f8cc257a32005ae9f8!OpenDocument | title = CB-13, MAM-2201, AKB48, and XLR11 are classified as temporary class drugs | date = 2012-07-05 | work = Temporary Class Drug Notice | publisher = The Department of Internal Affairs: New Zealand Gazette }}</ref>

The U.S. Drug Enforcement Administration (DEA) made XLR11 illegal under the Federal Controlled Substances act for the foreseeable future as of January 2024.<ref>{{Cite web |last=DEA |title= |url=https://www.deadiversion.usdoj.gov/schedules/orangebook/orangebook.pdf}}</ref>

It has also been banned in Florida as of 11 December 2012.<ref name="urlNews Release – Attorney General Pam Bondi Outlaws Additional Synthetic Drugs">{{cite press release | url = http://www.myfloridalegal.com/newsrel.nsf/newsreleases/C2FED4E8849E737685257AD1006EED54!OpenDocument | title = Attorney General Pam Bondi Outlaws Additional Synthetic Drugs | date = 2012-12-11 | publisher = State of Florida }}</ref>

Arizona banned XLR-11 on 3 April 2013.<ref>{{cite press release|publisher=Office of the Governor, State of Arizona |url=http://azgovernor.gov/dms/upload/PR_040313_SyntheticDrugs.pdf |title=Governor Jan Brewer Signs Legislation to Combat Production, Use of Dangerous Drugs |access-date=2014-08-27 |url-status=dead |archive-url=https://web.archive.org/web/20130607171024/http://azgovernor.gov/dms/upload/PR_040313_SyntheticDrugs.pdf |archive-date=7 June 2013 }}</ref>

As of October 2015 XLR-11 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=zh | access-date=1 October 2015}}</ref>

XLR-11 is banned in the Czech Republic.<ref>{{cite web | url=http://www.mzcr.cz/Admin/_upload/files/3/Nov%C3%A9%20PL.pdf | title=Látky, o které byl doplněn seznam č. 4 psychotropních látek (příloha č. 4 k nařízení vlády č. 463/2013 Sb.) | publisher=Ministerstvo zdravotnictví | language=cs}}</ref>

==Side effects==

XLR-11 has been linked to hospitalizations due to its use.<ref>{{cite journal | vauthors = Trecki J, Gerona RR, Schwartz MD | title = Synthetic Cannabinoid-Related Illnesses and Deaths | journal = The New England Journal of Medicine | volume = 373 | issue = 2 | pages = 103–107 | date = July 2015 | pmid = 26154784 | doi = 10.1056/NEJMp1505328 }}</ref>

==Toxicity==
XLR-11 has been linked to [[Medicine:Acute kidney injury|acute kidney injury]] in some users,<ref>{{cite web | url=http://dosemakespoison.blogspot.co.uk/2013/12/alphabet-soup-or-newer-synthetic.html | title=Alphabet Soup, or the newer synthetic cannabinoids... | publisher=The Dose Makes The Poison Blog | date=11 December 2013 | access-date=18 September 2014}}</ref> along with [[Chemistry:AM-2201|AM-2201]].<ref name="pmid23243266">{{cite journal | vauthors = Bhanushali GK, Jain G, Fatima H, Leisch LJ, Thornley-Brown D | title = AKI associated with synthetic cannabinoids: a case series | journal = Clinical Journal of the American Society of Nephrology | volume = 8 | issue = 4 | pages = 523–526 | date = April 2013 | pmid = 23243266 | pmc = 3613952 | doi = 10.2215/CJN.05690612 }}</ref><ref name="url_CDC">{{cite web | url = https://www.cdc.gov/mmwr/preview/mmwrhtml/mm6206a1.htm?s_cid=mm6206a1_x | title = Acute Kidney Injury Associated with Synthetic Cannabinoid Use – Multiple States, 2012 | date = 2013-02-15 | access-date = 2013-02-15 | work = Morbidity and Mortality Weekly Report | publisher = U.S. Centers for Disease Control and Prevention (CDC) }}</ref>

== See also ==
* [[Chemistry:FAB-144|FAB-144]]
* [[Chemistry:JWH-018|JWH-018]]
* [[Chemistry:STS-135 (drug)|STS-135]]
* [[Chemistry:UR-144|UR-144]]
* [[Chemistry:XLR-12|XLR-12]]

== References ==
{{reflist}}

{{Cannabinoids}}

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

{{Sourceattribution|XLR-11}}