RWJ-394674

RWJ-394674
Legal status
Legal status	In general: legal;
Identifiers
	IUPAC name N,N-diethyl-4-((8-phenethyl-8-azabicyclo[3.2.1]oct-3-ylidene)phenylmethyl)benzamide;
PubChem CID	10205965;
ChemSpider	23158278;
ChEMBL	ChEMBL68113;
Chemical and physical data
Formula	C33H38N2O
Molar mass	478.680 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCN(CC)C(=O)c1ccc(cc1)C(=C2C[C@H]3CC[C@@H](C2)N3CCc4ccccc4)c5ccccc5;
	InChI InChI=1S/C33H38N2O/c1-3-34(4-2)33(36)28-17-15-27(16-18-28)32(26-13-9-6-10-14-26)29-23-30-19-20-31(24-29)35(30)22-21-25-11-7-5-8-12-25/h5-18,30-31H,3-4,19-24H2,1-2H3/b32-29-/t30-,31+/m1/s1; Key:ZJOPBPNTQRUJNM-BPVGFELESA-N;
	(verify)

RWJ-394674 is a drug that is used in scientific research. It is a potent, orally active analgesic drug that produces little respiratory depression. RWJ-394674 itself is a potent and selective agonist for δ-opioid receptors, with a K_i of 0.24 nM at δ and 72 nM at μ. However once inside the body, RWJ-394674 is dealkylated to its monodesethyl metabolite RWJ-413216, which is a potent agonist at the μ-opioid receptor and has less affinity for δ (K_i of 0.26 nM at μ, 46.7 nM at δ). The effect of RWJ-394674 when administered in vivo thus produces potent agonist effects at both μ and δ receptors through the combined actions of the parent drug and its active metabolite, with the δ-agonist effects counteracting the respiratory depression from the μ-opioid effects, and the only prominent side-effect being sedation.^[1]

References

^ Codd EE, Carson JR, Colburn RW, Dax SL, Desai-Krieger D, Martinez RP, et al. (September 2006). "The novel, orally active, delta opioid RWJ-394674 is biotransformed to the potent mu opioid RWJ-413216". The Journal of Pharmacology and Experimental Therapeutics. 318 (3): 1273–9. doi:10.1124/jpet.106.104208. PMID 16766719. S2CID 13165519.

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[1] Codd EE, Carson JR, Colburn RW, Dax SL, Desai-Krieger D, Martinez RP, et al. (September 2006). "The novel, orally active, delta opioid RWJ-394674 is biotransformed to the potent mu opioid RWJ-413216". The Journal of Pharmacology and Experimental Therapeutics. 318 (3): 1273–9. doi:10.1124/jpet.106.104208. PMID 16766719. S2CID 13165519.

[1]

Legal status

Legal status	In general: legal
Identifiers
IUPAC name N,N-diethyl-4-((8-phenethyl-8-azabicyclo[3.2.1]oct-3-ylidene)phenylmethyl)benzamide
PubChem CID	10205965
ChemSpider	23158278
ChEMBL	ChEMBL68113
Chemical and physical data
Formula	C₃₃H₃₈N₂O
Molar mass	478.680 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CCN(CC)C(=O)c1ccc(cc1)C(=C2C[C@H]3CC[C@@H](C2)N3CCc4ccccc4)c5ccccc5
InChI InChI=1S/C33H38N2O/c1-3-34(4-2)33(36)28-17-15-27(16-18-28)32(26-13-9-6-10-14-26)29-23-30-19-20-31(24-29)35(30)22-21-25-11-7-5-8-12-25/h5-18,30-31H,3-4,19-24H2,1-2H3/b32-29-/t30-,31+/m1/s1 Key:ZJOPBPNTQRUJNM-BPVGFELESA-N
(verify)