DPI-3290

{{Short description|Chemical compound}}

{{Drugbox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 430788679

| IUPAC_name = 3-[(R)-[(2S,5R)-2,5-dimethyl-4-prop-2-enylpiperazin-1-yl]-(3-hydroxyphenyl)methyl]-N-(3-fluorophenyl)-N-methylbenzamide

| image = DPI-3290.svg

| image_class = skin-invert-image

| tradename =

| legal_status =

| CAS_number_Ref = {{cascite|changed|??}}

| CAS_number = 182417-73-8

| PubChem = 9826770

| UNII_Ref = {{fdacite|changed|FDA}}

| UNII = R3UO4Y068S

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 8002513

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 155892

| C=30 | H=34 | F=1 | N=3 | O=2

| 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

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = LZXRQLIIMYJZDA-UETOGOEVSA-N

}}

DPI-3290 was discovered by scientists at Burroughs Wellcome and licensed to Delta Pharmaceutical US Patent 5552404 - Opioid compounds and methods for using same and is a drug that is used in scientific research. It is a potent analgesic drug,{{cite journal | vauthors = Gengo PJ, Pettit HO, O'Neill SJ, Wei K, McNutt R, Bishop MJ, Chang KJ | title = 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 | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 307 | issue = 3 | pages = 1221–6 | date = December 2003 | pmid = 14534368 | doi = 10.1124/jpet.103.054361 | s2cid = 93569860 }} which produces little respiratory depression.{{cite journal | vauthors = Gengo PJ, Pettit HO, O'Neill SJ, Su YF, McNutt R, Chang KJ | title = 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 | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 307 | issue = 3 | pages = 1227–33 | date = December 2003 | pmid = 14534367 | doi = 10.1124/jpet.103.054429 | s2cid = 45159720 }}

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.{{cite journal | vauthors = Ananthan S | title = Opioid ligands with mixed mu/delta opioid receptor interactions: an emerging approach to novel analgesics | journal = The AAPS Journal | volume = 8 | issue = 1 | pages = E118-25 | date = March 2006 | pmid = 16584118 | pmc = 2751430 | doi = 10.1208/aapsj080114 }}