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Details

Stereochemistry ACHIRAL
Molecular Formula C23H30N2O
Molecular Weight 350.498
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BUTYRFENTANYL

SMILES

CCCC(=O)N(c1ccccc1)C2CCN(CCc3ccccc3)CC2

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

HIDE SMILES / InChI

Description
Curator's Comment:: https://www.ncbi.nlm.nih.gov/pubmed/26083809 | https://www.ncbi.nlm.nih.gov/pubmed/27289433 | https://www.ncbi.nlm.nih.gov/pubmed/26683128

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.

Approval Year

PubMed

PubMed

TitleDatePubMed
Patents

Patents

Sample Use Guides

0.5 mg to 3 mg
Route of Administration: Nasal
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
Name Type Language
BUTYRFENTANYL
Common Name English
N-(1-PHENETHYL-4-PIPERIDYL)-N-PHENYL-BUTANAMIDE
Systematic Name English
NIH-10486 FREE BASE
Code English
BUTYR-FENTANYL
Common Name English
N-BUTYRYLFENTANYL
Common Name English
BUTANAMIDE, N-PHENYL-N-(1-(2-PHENYLETHYL)-4-PIPERIDINYL)-
Systematic Name English
N-PHENYL-N-(1-(2-PHENYLETHYL)-4-PIPERIDINYL)BUTANAMIDE
Systematic Name English
Classification Tree Code System Code
WIKIPEDIA List_of_fentanyl_analogues
Created by admin on Sat Jun 26 04:46:34 UTC 2021 , Edited by admin on Sat Jun 26 04:46:34 UTC 2021
DEA NO. 9822
Created by admin on Sat Jun 26 04:46:34 UTC 2021 , Edited by admin on Sat Jun 26 04:46:34 UTC 2021
Code System Code Type Description
CAS
1169-70-6
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PRIMARY
PUBCHEM
621174
Created by admin on Sat Jun 26 04:46:34 UTC 2021 , Edited by admin on Sat Jun 26 04:46:34 UTC 2021
PRIMARY
WIKIPEDIA
BUTYRFENTANYL
Created by admin on Sat Jun 26 04:46:34 UTC 2021 , Edited by admin on Sat Jun 26 04:46:34 UTC 2021
PRIMARY Butyrfentanyl has no current legitimate clinical applications, however it is being sold as designer drug. Butyrfentanyl is illegal in the United Kingdom as it is a modification of fentanyl "by replacement of the N-propionyl group by another acyl group". One of the first mentions of this drug can be found in document written by The College on Problem of Drug Dependence, where it is mentioned as N-butyramide fentanyl analog. This document also states that the article describing its clinical effects (analgesic studies, m-, d-, k-Opioid receptor binding and in vitro measures of drug efficacy, antinociceptive and narcotic properties) was published in 1987. It is an agonist for the .MU.-opioid receptors.
FDA UNII
07V1H7R6ZN
Created by admin on Sat Jun 26 04:46:34 UTC 2021 , Edited by admin on Sat Jun 26 04:46:34 UTC 2021
PRIMARY
WEB RESOURCE
BUTYRFENTANYL
Created by admin on Sat Jun 26 04:46:34 UTC 2021 , Edited by admin on Sat Jun 26 04:46:34 UTC 2021
PRIMARY
EPA CompTox
1169-70-6
Created by admin on Sat Jun 26 04:46:34 UTC 2021 , Edited by admin on Sat Jun 26 04:46:34 UTC 2021
PRIMARY
DRUG BANK
DB09173
Created by admin on Sat Jun 26 04:46:34 UTC 2021 , Edited by admin on Sat Jun 26 04:46:34 UTC 2021
PRIMARY
EVMPD
SUB180956
Created by admin on Sat Jun 26 04:46:34 UTC 2021 , Edited by admin on Sat Jun 26 04:46:34 UTC 2021
PRIMARY