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Details

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
Structure of BUTYRFENTANYL

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

HIDE SMILES / InChI

Molecular Formula C23H30N2O
Molecular Weight 350.4971
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: The description was created based on several sources, including 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
Time-dependent postmortem redistribution of butyrfentanyl and its metabolites in blood and alternative matrices in a case of butyrfentanyl intoxication.
2016 Sep
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
Substance Class Chemical
Created
by admin
on Thu Jul 06 17:22:03 UTC 2023
Edited
by admin
on Thu Jul 06 17:22:03 UTC 2023
Record UNII
07V1H7R6ZN
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BUTYRFENTANYL
Common Name English
FENTANYL BUTYRYL ANALOG
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
BUTYRLFENTANYL
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
N-(1-PHENETHYLPIPERIDIN-4-YL)-N-PHENYLBUTYRAMIDE
Systematic Name English
Classification Tree Code System Code
WIKIPEDIA List_of_fentanyl_analogues
Created by admin on Thu Jul 06 17:22:03 UTC 2023 , Edited by admin on Thu Jul 06 17:22:03 UTC 2023
WIKIPEDIA Designer-drugs-Butyrfentanyl
Created by admin on Thu Jul 06 17:22:03 UTC 2023 , Edited by admin on Thu Jul 06 17:22:03 UTC 2023
DEA NO. 9822
Created by admin on Thu Jul 06 17:22:03 UTC 2023 , Edited by admin on Thu Jul 06 17:22:03 UTC 2023
Code System Code Type Description
CAS
1169-70-6
Created by admin on Thu Jul 06 17:22:03 UTC 2023 , Edited by admin on Thu Jul 06 17:22:03 UTC 2023
PRIMARY
PUBCHEM
621174
Created by admin on Thu Jul 06 17:22:03 UTC 2023 , Edited by admin on Thu Jul 06 17:22:03 UTC 2023
PRIMARY
WIKIPEDIA
BUTYRFENTANYL
Created by admin on Thu Jul 06 17:22:03 UTC 2023 , Edited by admin on Thu Jul 06 17:22:03 UTC 2023
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.
SMS_ID
100000166697
Created by admin on Thu Jul 06 17:22:03 UTC 2023 , Edited by admin on Thu Jul 06 17:22:03 UTC 2023
PRIMARY
FDA UNII
07V1H7R6ZN
Created by admin on Thu Jul 06 17:22:03 UTC 2023 , Edited by admin on Thu Jul 06 17:22:03 UTC 2023
PRIMARY
WEB RESOURCE
BUTYRFENTANYL
Created by admin on Thu Jul 06 17:22:03 UTC 2023 , Edited by admin on Thu Jul 06 17:22:03 UTC 2023
PRIMARY
EPA CompTox
DTXSID30347410
Created by admin on Thu Jul 06 17:22:03 UTC 2023 , Edited by admin on Thu Jul 06 17:22:03 UTC 2023
PRIMARY
DRUG BANK
DB09173
Created by admin on Thu Jul 06 17:22:03 UTC 2023 , Edited by admin on Thu Jul 06 17:22:03 UTC 2023
PRIMARY
EVMPD
SUB180956
Created by admin on Thu Jul 06 17:22:03 UTC 2023 , Edited by admin on Thu Jul 06 17:22:03 UTC 2023
PRIMARY
Related Record Type Details
TARGET -> AGONIST
BINDING
Ki
TARGET -> AGONIST
EC50
SALT/SOLVATE -> PARENT
Related Record Type Details
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Related Record Type Details
ACTIVE MOIETY
ED50(mg/kg) = 0.047, Potency ratio to morphine = 7.0, Potency ratio to fentanyl = 0.13