XLR-11
{{Short description|Chemical compound}}
{{about|the recreational drug|the rocket motor|Reaction Motors XLR11}}
{{Use dmy dates|date=January 2022}}
{{Drugbox
| drug_name =
| IUPAC_name = (1-(5-fluoropentyl)-1H-indol-3-yl)(2,2,3,3-tetramethylcyclopropyl)methanone
| image = XLR-11_structure.png
| image_class = skin-invert-image
| tradename =
| pregnancy_AU =
| pregnancy_US =
| pregnancy_category =
| legal_AU =
| legal_BR = F2
| legal_BR_comment = {{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2023-07-24 |title=RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-804-de-24-de-julho-de-2023-498447451 |url-status=live |archive-url=https://web.archive.org/web/20230827163149/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-804-de-24-de-julho-de-2023-498447451 |archive-date=2023-08-27 |access-date=2023-08-27 |publisher=Diário Oficial da União |language=pt-BR |publication-date=2023-07-25}}
| 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 =
| bioavailability =
| protein_bound =
| metabolism =
| elimination_half-life =
| excretion =
| 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
| 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 agonist for the cannabinoid receptors CB1 and CB2 with EC50 values of 98 nM and 83 nM, respectively.{{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 }} It is a 3-(tetramethylcyclopropylmethanoyl)indole derivative related to compounds such as UR-144, A-796,260 and A-834,735, but it is not specifically listed in the patent or scientific literature alongside these other similar compounds,{{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 }}{{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 }} and appears to have not previously been made by 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 mg/kg and 10 mg/kg, suggesting that it is of comparable potency to APICA and STS-135.
Detection
A forensic standard for this compound is available, and a representative mass spectrum has been posted on 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) }}
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.{{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 }}
Legal Status
XLR-11 was banned in New Zealand by being added to the temporary class drug schedule, {{as of|lc=y|2012|07|13}}.{{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 }}
The U.S. Drug Enforcement Administration (DEA) made XLR11 illegal under the Federal Controlled Substances act for the foreseeable future {{as of|lc=y|2024|01}}.{{Cite web |last=DEA |title=Lists of: Scheduling Actions, Controlled Substances, Regulated Chemicals |date=April 2024 |access-date=2024-05-13 |archive-url=https://web.archive.org/web/20240505071610/https://www.deadiversion.usdoj.gov/schedules/orangebook/orangebook.pdf |archive-date=2024-05-05 |url=https://www.deadiversion.usdoj.gov/schedules/orangebook/orangebook.pdf}}
It has also been banned in Florida {{as of|2012|12|11|lc=y}}.{{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 }}
{{As of|2015|10}}, XLR-11 is a controlled substance in China.{{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}}
XLR-11 is banned in the Czech Republic.{{as of?|date=May 2024}}{{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}}
Side effects
XLR-11 has been linked to hospitalizations due to its use.{{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 }}
Toxicity
XLR-11 has been linked to acute kidney injury in some users,{{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}} along with AM-2201.{{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 }}{{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) }}