DPI-3290

DPI-3290

Systematic (IUPAC) name
(+)-3-((αR)-α-((2S,5R)-4-Allyl-2,5-dimethyl-1-piperazinyl)-3-hydroxybenzyl)-N-(3-fluorophenyl)-N-methylbenzamide
Identifiers
CAS Number	182417-73-8
PubChem	CID 5242141
Chemical data
Formula	C30H34FN3O2
Molar mass	487.607 g/mol
SMILES OC1=CC=CC([C@@](C2=CC(C(N(C3=CC(F)=CC=C3)C)=O)=CC=C2)([H])N([C@@H](CN4CC=C)C)C[C@@H]4C)=C1
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DPI-3290 was discovered by Delta Pharmaceutical ^[1] and is a drug that is used in scientific research. It is a potent analgesic drug,^[2] which produces little respiratory depression.^[3]

DPI-3290 acts as an agonist at both μ- and δ-opioid receptor, with an IC50 of 6.2nM at μ and 1.0nM at δ.^[4]

References

1. US Patent 5552404 - Opioid compounds and methods for using same
2. Gengo, PJ; Pettit, HO; O'Neill, SJ; Wei, K; McNutt, R; Bishop, MJ; Chang, KJ (2003). "DPI-3290 (+)-3-((alpha-R)-alpha-((2S,5R)-4-allyl-2,5-dimethyl-1-piperazinyl)-3-hydroxybenzyl)-N-(3-fluorophenyl)-N-methylbenzamide. I. A mixed opioid agonist with potent antinociceptive activity". The Journal of Pharmacology and Experimental Therapeutics 307 (3): 1221–6. doi:10.1124/jpet.103.054361. PMID 14534368.
3. Gengo, PJ; Pettit, HO; O'Neill, SJ; Su, YF; McNutt, R; Chang, KJ (2003). "DPI-3290 (+)-3-((alpha-R)-alpha-((2S,5R)-4-Allyl-2,5-dimethyl-1-piperazinyl)-3-hydroxybenzyl)-N-(3-fluorophenyl)-N-methylbenzamide. II. A mixed opioid agonist with potent antinociceptive activity and limited effects on respiratory function". The Journal of Pharmacology and Experimental Therapeutics 307 (3): 1227–33. doi:10.1124/jpet.103.054429. PMID 14534367.
4. Ananthan, S (Mar 2006). "Opioid ligands with mixed mu/delta opioid receptor interactions: an emerging approach to novel analgesics". AAPS Journal 8 (1): E118–25. doi:10.1208/aapsj080114. PMC 2751430. PMID 16584118.