O-4310

O-4310
Clinical data
Other namesO4310; 1-Isopropyl-6-fluoropsilocin
Drug classSerotonin 5-HT2A receptor agonist
Identifiers
IUPAC name
  • 3-[2-(dimethylamino)ethyl]-6-fluoro-1-isopropyl-1H-indol-4-ol
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC15H21FN2O
Molar mass264.344 g·mol−1
3D model (JSmol)
SMILES
  • CC(C)N1C2=CC(F)=CC(O)=C2C(CCN(C)C)=C1
InChI
  • InChI=1S/C15H21FN2O/c1-10(2)18-9-11(5-6-17(3)4)15-13(18)7-12(16)8-14(15)19/h7-10,19H,5-6H2,1-4H3
  • Key:PAUIFMSQKOHMQT-UHFFFAOYSA-N

O-4310, also known as 1-isopropyl-6-fluoropsilocin, is a serotonin receptor agonist of the tryptamine family.[1][2] It is the 1-isopropylated and 6-flourinated derivative of the serotonergic psychedelic psilocin.[2]

Pharmacology

The drug is said to be a serotonin 5-HT2A receptor agonist and to be highly selective for activation of this receptor over the closely related serotonin 5-HT2B and 5-HT2C receptors.[2] Its EC50Tooltip half-maximal effective concentration at the serotonin 5-HT2A receptor was reported to be 5 nM and it was said to have an EmaxTooltip maximal efficacy of 89% relative to serotonin.[2] Conversely, O-4310 was said to be inactive at the serotonin 5-HT2B receptor, with no EC50 or Emax reported for this receptor, and was claimed to have an EC50 of 592 nM at the serotonin 5-HT2C receptor with an Emax of approximately 50%.[2] Hence, O-4310 appears to show about 118-fold selectivity for activation of the serotonin 5-HT2A receptor over the serotonin 5-HT2C receptor.[2]

The pharmacodynamic activity of O-4310 was briefly described in a patent but not in the published scientific literature.[2][1] If the reported data are accurate, O-4310, along with other drugs like 25CN-NBOH and (S,S)-DMBMPP, would be one of the most selective known agonists of the serotonin 5-HT2A receptor over the other serotonin 5-HT2 receptors.[3]

History

O-4310 was patented by Bryan Roth and colleagues in 2006 and the patent was assigned to the American pharmaceutical company Organix Inc as well as a couple of other assignees.[2] The drug was also employed in an animal study and described in the scientific literature by a group of Iranian researchers in 2017.[1]

See also

References

  1. 1 2 3 Motaghinejad O, Motaghinejad M, Motevalian M, Rahimi-Sharbaf F, Beiranvand T (October 2017). "The effect of maternal forced exercise on offspring pain perception, motor activity and anxiety disorder: the role of 5-HT2 and D2 receptors and CREB gene expression". Journal of Exercise Rehabilitation. 13 (5): 514–525. doi:10.12965/jer.1734992.496. PMC 5667597. PMID 29114525.
  2. 1 2 3 4 5 6 7 8 [url=https://patents.google.com/patent/US7655691B2/ US 7655691], Kumaran G, Morency C, Roth B, Sard HP, Shuster L Xu L, "Indole compounds useful as serotonin selective agents.", published 11 May 2006, assigned to Organix Inc and Tufts University, Case Western Reserve University
  3. ↑ Poulie CB, Jensen AA, Halberstadt AL, Kristensen JL (December 2020). "DARK Classics in Chemical Neuroscience: NBOMes". ACS Chem Neurosci. 11 (23): 3860–3869. doi:10.1021/acschemneuro.9b00528. PMC 9191638. PMID 31657895. The psychedelic phenethylamines typically exhibit less than 5–10-fold selectivity for 5-HT2A over 5-HT2C receptors.53,54 Notable exceptions include (S,S)-DMBMPP and 25CN-NBOH (Figure 3), which are the most selective 5-HT2AR agonists published to date.49,58–61 (S,S)-DMBMPP exhibits more than 100-fold higher binding affinity for the 5-HT2AR over 5-HT2CR, and 25CN-NBOH has substantially higher agonist potencies at 5-HT2AR compared to 5-HT2CR.
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