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Details

Stereochemistry ACHIRAL
Molecular Formula C23H30N2O.ClH
Molecular Weight 386.958
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BUTYRFENTANYL HYDROCHLORIDE

SMILES

Cl.CCCC(=O)N(C1CCN(CCC2=CC=CC=C2)CC1)C3=CC=CC=C3

InChI

InChIKey=OHCXSXCINRZXIB-UHFFFAOYSA-N
InChI=1S/C23H30N2O.ClH/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;1H

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

Molecular Formula ClH
Molecular Weight 36.461
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 Sat Dec 16 11:45:15 UTC 2023
Edited
by admin
on Sat Dec 16 11:45:15 UTC 2023
Record UNII
2QEJ9R6PK4
Record Status Validated (UNII)
Record Version
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Name Type Language
BUTYRFENTANYL HYDROCHLORIDE
Common Name English
BUTYRFENTANYL MONOHYDROCHLORIDE
Common Name English
BUTANAMIDE, N-PHENYL-N-(1-(2-PHENYLETHYL)-4-PIPERIDINYL)-, MONOHYDROCHLORIDE
Systematic Name English
BUTANAMIDE, N-PHENYL-N-(1-(2-PHENYLETHYL)-4-PIPERIDINYL)-, HYDROCHLORIDE (1:1)
Systematic Name English
NIH 10486
Code English
NIH-10486
Code English
BUTYRYL FENTANYL (HYDROCHLORIDE)
Common Name English
N-(1-PHENETHYL-4-PIPERIDYL)-BUTYRANILIDE, HYDROCHLORIDE
Systematic Name English
Code System Code Type Description
CAS
1443-52-3
Created by admin on Sat Dec 16 11:45:15 UTC 2023 , Edited by admin on Sat Dec 16 11:45:15 UTC 2023
PRIMARY
FDA UNII
2QEJ9R6PK4
Created by admin on Sat Dec 16 11:45:15 UTC 2023 , Edited by admin on Sat Dec 16 11:45:15 UTC 2023
PRIMARY
EPA CompTox
DTXSID101036720
Created by admin on Sat Dec 16 11:45:15 UTC 2023 , Edited by admin on Sat Dec 16 11:45:15 UTC 2023
PRIMARY
PUBCHEM
118796521
Created by admin on Sat Dec 16 11:45:15 UTC 2023 , Edited by admin on Sat Dec 16 11:45:15 UTC 2023
PRIMARY
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