F-17475

F-17475 is an NMDA receptor antagonist described as an analgesic, which was under development for the treatment of postoperative pain but was never marketed.^[1]

F-17475

Clinical data
Drug class	NMDA receptor antagonist; Analgesic; Dissociative; Hallucinogen
ATC code	None
Identifiers
IUPAC name (1R,3R)-3-amino-N,N-diethyl-1-phenylcyclobutane-1-carboxamide
CAS Number	1612885-86-5
PubChem CID	76071622
ChemSpider	70099827
Chemical and physical data
Formula	C15H22N2O
Molar mass	246.354 g·mol−1
3D model (JSmol)	Interactive image
SMILES CCN(CC)C(=O)[C@@]1(C[C@@H](N)C1)c1ccccc1
InChI InChI=1S/C15H22N2O/c1-3-17(4-2)14(18)15(10-13(16)11-15)12-8-6-5-7-9-12/h5-9,13H,3-4,10-11,16H2,1-2H3 Key:OVAIACNINHMYRO-UHFFFAOYSA-N

The drug shows similar affinity for the NMDA receptor as ketamine (K_i = 0.74 and 1.05 μM, respectively).^[1] It shows analgesic effects in rodents, with about twice the potency of ketamine, and potentiates morphine-induced analgesia.^[1] F-17475 substitutes for ketamine in rodent drug discrimination tests, suggesting that it may have dissociative hallucinogen effects in humans.^[1] However, F-17475 showed a greater margin of analgesic to dissociative-like effects than ketamine in rodents.^[1]

F-17475 was first described in the patent literature by 2012, developed by researchers at Pierre Fabre. The m-chloro derivative is slightly more potent, up to 10x stronger than ketamine, but had a less favorable side effect profile in animal tests.^[2]