XLR-11

This article is about the recreational drug. For the rocket motor, see Reaction Motors XLR11.

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.^[2] 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,^[3][4] 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.^[2]

XLR-11

Legal status
Legal status	BR: Class F2 (Prohibited psychotropics)[1] CA: Schedule II DE: Anlage II (Authorized trade only, not prescriptible) NZ: Temporary Class UK: Class B US: Schedule I
Identifiers
IUPAC name (1-(5-fluoropentyl)-1H-indol-3-yl)(2,2,3,3-tetramethylcyclopropyl)methanone
CAS Number	1364933-54-9 Y
PubChem CID	57501498
ChemSpider	28537382
UNII	L2M8B977ZE
KEGG	C22770
CompTox Dashboard (EPA)	DTXSID00159825
Chemical and physical data
Formula	C21H28FNO
Molar mass	329.459 g·mol−1
3D model (JSmol)	Interactive image
SMILES CC1(C(C1(C)C)C(=O)c2cn(c3c2cccc3)CCCCCF)C
InChI InChI=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 Key:PXLDPUUMIHVLEC-UHFFFAOYSA-N

Detection

A forensic standard for this compound is available, and a representative mass spectrum has been posted on Forendex.^[5]

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.^[6]

Legal Status

XLR-11 was banned in New Zealand by being added to the temporary class drug schedule, as of 13 July 2012^[update].^[7]

The U.S. Drug Enforcement Administration (DEA) made XLR11 illegal under the Federal Controlled Substances act for the foreseeable future as of January 2024^[update].^[8]

It has also been banned in Florida as of 11 December 2012^[update].^[9]

Arizona banned XLR-11 on 3 April 2013.^[10]

As of October 2015^[update], XLR-11 is a controlled substance in China.^[11]

XLR-11 is banned in the Czech Republic.^{[as of?][12]}

Side effects

XLR-11 has been linked to hospitalizations due to its use.^[13]

Toxicity

XLR-11 has been linked to acute kidney injury in some users,^[14] along with AM-2201.^[15][16]

See also

• FAB-144
• JWH-018
• STS-135
• UR-144
• XLR-12