| Stereochemistry | ACHIRAL |
| Molecular Formula | C23H30N2O |
| Molecular Weight | 350.4971 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CCCC(=O)N(C1CCN(CCC2=CC=CC=C2)CC1)C3=CC=CC=C3
InChI
InChIKey=QQOMYEQLWQJRKK-UHFFFAOYSA-N
InChI=1S/C23H30N2O/c1-2-9-23(26)25(21-12-7-4-8-13-21)22-15-18-24(19-16-22)17-14-20-10-5-3-6-11-20/h3-8,10-13,22H,2,9,14-19H2,1H3
| Molecular Formula | C23H30N2O |
| Molecular Weight | 350.4971 |
| Charge | 0 |
| Count |
MOL RATIO
1 MOL RATIO (average) |
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
DB09173 (Butyrfentanyl or butyrylfentanyl) is a potent, short-acting mu opioid receptor agonist, and an analog of fentanyl, differing by only one methyl group. It has no approved medical indications but is being used for recreational purposes, with cases of fatal overdoses reported in Europe and the United States. Pre-clinical studies of butyrfentanyl are scarce; however, the few available studies suggest that butyrfentanyl is about 30 times less potent than fentanyl itself, and has significant antinociceptive properties, as demonstrated by the acetic acid writhing test in rodents. DB09173 is being abused for its opioid effects. As with other mu-opioid agonists, it can induce respiratory depression which may lead to death and numerous deaths have been reported. No studies of butyrfentanyl dependence or cross-dependence conducted in humans could be identified.
CNS Activity
Originator
Approval Year
PubMed
Patents
Sample Use Guides
Microsomal incubation mixture (final volume, 50 μL) contained 100mMphosphate buffer (pH7.4), 200 U/mL superoxide dismutase (SOD), 100 μM butyrfentanyl, regenerating system (glucose 6-phosphate (G6P) 5mM, glucose 6-phosphate dehydrogenase (G6PD) 0.5 U/mL, nicotinamide adenine dinucleotide (NADP+) 1.2mM and MgCl2 5mM) and 1mg/mL pooled human liver microsomes (HLM, from 20 different donors). Negative control was performed with butyrfentanyl but without HLMs. Methanol concentration in the assays was always kept below 0.1%. Reactions were started by adding the enzyme. After incubating at 37 °C for 30 min, the reactions were stopped by addition of 50 μL of acetonitrile. The sample was then centrifuged (10,000 rpm, 20min), the supernatant was transferred to an autosampler vial and analyzed by LC-QTOF-MS
