(R)-69

(R)-69
Clinical data
Other names	3IQ
Identifiers
	IUPAC name 3-[(5R)-5-methyl-1,2,5,6-tetrahydropyridin-3-yl]-1H-pyrrolo[2,3-b]pyridine;
PubChem CID	164513426;
Chemical and physical data
Formula	C13H15N3
Molar mass	213.284 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C[C@@H]1C=C(CNC1)c1c[NH]c2ncccc12;
	InChI InChI=1S/C13H15N3/c1-9-5-10(7-14-6-9)12-8-16-13-11(12)3-2-4-15-13/h2-5,8-9,14H,6-7H2,1H3,(H,15,16)/t9-/m1/s1; Key:HNDPIXZRQWKEFZ-SECBINFHSA-N;

(R)-69 (3IQ) is a tetrahydropyridine derivative which acts as a 5-HT_2A receptor agonist, with 4.6-fold selectivity over 5-HT_2B and 49-fold selectivity over 5-HT_2C. It has a 5-HT_2A K_i of 680 nM and an EC₅₀ of 41 nM. (R)-69 is a biased agonist selective for activation of the G_q coupled signalling pathway, with much weaker activation of the β-arrestin 2 coupled pathway. In animal studies it produces antidepressant-like activity but without producing the head-twitch response associated with psychedelic effects.^[1]

References

^ Kaplan AL, Confair DN, Kim K, Barros-Álvarez X, Rodriguiz RM, Yang Y, et al. (September 2022). "Bespoke library docking for 5-HT_2A receptor agonists with antidepressant activity". Nature. 610 (7932): 582–591. Bibcode:2022Natur.610..582K. doi:10.1038/s41586-022-05258-z. PMC 9996387. PMID 36171289. S2CID 252598838.

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[1] Kaplan AL, Confair DN, Kim K, Barros-Álvarez X, Rodriguiz RM, Yang Y, et al. (September 2022). "Bespoke library docking for 5-HT_2A receptor agonists with antidepressant activity". Nature. 610 (7932): 582–591. Bibcode:2022Natur.610..582K. doi:10.1038/s41586-022-05258-z. PMC 9996387. PMID 36171289. S2CID 252598838.

[1]

Clinical data

Other names	3IQ
Identifiers
IUPAC name 3-[(5R)-5-methyl-1,2,5,6-tetrahydropyridin-3-yl]-1H-pyrrolo[2,3-b]pyridine
PubChem CID	164513426
Chemical and physical data
Formula	C₁₃H₁₅N₃
Molar mass	213.284 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES C[C@@H]1C=C(CNC1)c1c[NH]c2ncccc12
InChI InChI=1S/C13H15N3/c1-9-5-10(7-14-6-9)12-8-16-13-11(12)3-2-4-15-13/h2-5,8-9,14H,6-7H2,1H3,(H,15,16)/t9-/m1/s1 Key:HNDPIXZRQWKEFZ-SECBINFHSA-N

(R)-69

See also

References