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AB-5'F-BUTINACA

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AB-5'F-BUTINACA
Clinical data
Drug classCannabinoid CB1 receptor agonist
ATC code
  • None
Identifiers
  • N-(1-amino-3-methyl-1-oxobutan-2-yl)-1-butyl-5-fluoroindazole-3-carboxamide
PubChem CID
Chemical and physical data
FormulaC17H23FN4O2
Molar mass334.395 g·mol−1
3D model (JSmol)
  • CCCCN1C2=C(C=C(C=C2)F)C(=N1)C(=O)NC(C(C)C)C(=O)N
  • InChI=1S/C17H23FN4O2/c1-4-5-8-22-13-7-6-11(18)9-12(13)15(21-22)17(24)20-14(10(2)3)16(19)23/h6-7,9-10,14H,4-5,8H2,1-3H3,(H2,19,23)(H,20,24)
  • Key:INFPTRNVDSIRRH-UHFFFAOYSA-N

AB-5'F-BUTINACA is a synthetic cannabinoid of the indazole family.[1][2]

It is a potent full agonist of the cannabinoid CB1 receptor, with an EC50Tooltip half-maximal effective concentration of 18.7 nM and an EmaxTooltip maximal efficacy relative to JWH-018 of 107%.[1] In addition to its cannabinoid CB1 receptor agonism, AB-5'F-BUTINACA is also a very-low-potency serotonin 5-HT2A receptor partial agonist, with an EC50 of greater than 10,000 nM and an Emax relative to LSD of 67.3%.[2] The drug was the most efficacious serotonin 5-HT2A receptor agonist of a series of assessed synthetic cannabinoids.[2] However, due to its very low potency, this action may not be pharmacologically relevant.[2]

AB-5'F-BUTINACA produces effects in rodents including neurological changes, sensorimotor alterations, analgesia, hypothermia, bradypnea, hypolocomotion, convulsions, and hyperreflexia.[2] These effects can be variably reversed by the selective cannabinoid CB1 receptor antagonist NESS-0327 and by the selective serotonin 5-HT2A receptor antagonist volinanserin (MDL-100907).[2] The drug did not produce the head-twitch response, a behavioral proxy of psychedelic effects, in rodents.[2] It is said to be unclear whether the serotonin 5-HT2A receptor involvement in AB-5'F-BUTINACA's effects is due to direct interaction with this receptor or mere endocannabinoid system modulation of the serotonin system.[2]

The chemical synthesis of AB-5'F-BUTINACA has been described.[1]

AB-5'F-BUTINACA was first described in the scientific literature by 2025.[1]

See also

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References

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  1. 1 2 3 4 Green H, McKenzie C, Hamra E, Rautio T, Wu X, Juneskog E, et al. (August 2025). "In vitro CB1 receptor activity of halogenated indazole synthetic cannabinoid receptor agonists". Archives of Toxicology. 99 (8): 3343–3353. doi:10.1007/s00204-025-04082-4. PMC 12367851. PMID 40382747.
  2. 1 2 3 4 5 6 7 8 Corli G, Rudin D, Luethi D, Liechti ME, Bilel S, Marti M, et al. (May 2026). "5-HT2A receptor agonism by tert-leucinamide and valinamide synthetic cannabinoids: In vitro and in vivo evidence". British Journal of Pharmacology bph.70457. doi:10.1111/bph.70457. PMID 42086516.
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