(R)-69

Chemical compound From Wikipedia, the free encyclopedia

(R)-69 (3IQ) is a drug of the tetrahydropyridinylpyrrolopyridine family related to the psychedelic tryptamines which acts as a 5-HT2A receptor agonist, with 4.6-fold selectivity over 5-HT2B and 49-fold selectivity over 5-HT2C.[1][2] It has a 5-HT2A Ki of 680 nM and an EC50 of 41 nM.[1][2] (R)-69 is a biased agonist selective for activation of the Gq coupled signalling pathway, with much weaker activation of the β-arrestin 2 coupled pathway.[1][2][3] In animal studies it produces antidepressant-like activity but without producing the head-twitch response associated with psychedelic effects.[1][2] The drug was identified along with its close analogue (R)-70 via an ultra-large-scale docking campaign against the serotonin 5-HT2A receptor and was first described by Bryan L. Roth and colleagues in 2022.[1][2] A number of related derivatives have also been developed.[4][5]

Other namesR-69; 3IQ
CAS Number
Quick facts Clinical data, Other names ...
(R)-69
Clinical data
Other namesR-69; 3IQ
Drug classNon-hallucinogenic Serotonin 5-HT2A receptor agonist
Identifiers
  • 3-[(5R)-5-methyl-1,2,5,6-tetrahydropyridin-3-yl]-1H-pyrrolo[2,3-b]pyridine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
Chemical and physical data
FormulaC13H15N3
Molar mass213.284 g·mol−1
3D model (JSmol)
  • C[C@@H]1C=C(CNC1)c1c[NH]c2ncccc12
  • 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
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