en DPI-3290

DPI-3290
Identifiers
	IUPAC name 3-[(R)-[(2S,5R)-2,5-dimethyl-4-prop-2-enylpiperazin-1-yl]-(3-hydroxyphenyl)methyl]-N-(3-fluorophenyl)-N-methylbenzamide;
CAS Number	182417-73-8 ;
PubChem CID	9826770;
ChemSpider	8002513 ;
UNII	R3UO4Y068S;
ChEMBL	ChEMBL155892 ;
Chemical and physical data
Formula	C30H34FN3O2
Molar mass	487.619 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C[C@H]1CN([C@@H](CN1[C@@H](C2=CC(=CC=C2)O)C3=CC=CC(=C3)C(=O)N(C)C4=CC(=CC=C4)F)C)CC=C;
	InChI InChI=1S/C30H34FN3O2/c1-5-15-33-19-22(3)34(20-21(33)2)29(24-10-7-14-28(35)17-24)23-9-6-11-25(16-23)30(36)32(4)27-13-8-12-26(31)18-27/h5-14,16-18,21-22,29,35H,1,15,19-20H2,2-4H3/t21-,22+,29-/m1/s1 ; Key:LZXRQLIIMYJZDA-UETOGOEVSA-N ;
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DPI-3290 was discovered by scientists at Burroughs Wellcome and licensed to 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

^ US Patent 5552404 - Opioid compounds and methods for using same
^ Gengo PJ, Pettit HO, O'Neill SJ, Wei K, McNutt R, Bishop MJ, Chang KJ (December 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. S2CID 93569860.
^ Gengo PJ, Pettit HO, O'Neill SJ, Su YF, McNutt R, Chang KJ (December 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. S2CID 45159720.
^ Ananthan S (March 2006). "Opioid ligands with mixed mu/delta opioid receptor interactions: an emerging approach to novel analgesics". The AAPS Journal. 8 (1): E118-25. doi:10.1208/aapsj080114. PMC 2751430. PMID 16584118.

[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 (December 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. S2CID 93569860.

[3] Gengo PJ, Pettit HO, O'Neill SJ, Su YF, McNutt R, Chang KJ (December 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. S2CID 45159720.

[4] Ananthan S (March 2006). "Opioid ligands with mixed mu/delta opioid receptor interactions: an emerging approach to novel analgesics". The AAPS Journal. 8 (1): E118-25. doi:10.1208/aapsj080114. PMC 2751430. PMID 16584118.

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DPI-3290

See also

References