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
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
DescriptionSources: https://www.drugbank.ca/drugs/DB09173Curator'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
Sources: https://www.drugbank.ca/drugs/DB09173
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.
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL233 |
2.34 nM [IC50] | ||
Target ID: CHEMBL236 |
469.0 nM [IC50] | ||
Target ID: CHEMBL237 |
429.0 nM [IC50] | ||
Target ID: CHEMBL2858 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28807672 |
18.0 nM [Ki] | ||
Target ID: CHEMBL3222 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28807672 |
286.0 nM [Ki] | ||
Target ID: CHEMBL4329 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28807672 |
3174.0 nM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26083809
0.5 mg to 3 mg
Route of Administration:
Nasal
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27736030
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 | ||
---|---|---|---|---|
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Systematic Name | English | ||
|
Systematic Name | English |
Classification Tree | Code System | Code | ||
---|---|---|---|---|
|
WIKIPEDIA |
List_of_fentanyl_analogues
Created by
admin on Sat Dec 16 11:45:12 GMT 2023 , Edited by admin on Sat Dec 16 11:45:12 GMT 2023
|
||
|
WIKIPEDIA |
Designer-drugs-Butyrfentanyl
Created by
admin on Sat Dec 16 11:45:12 GMT 2023 , Edited by admin on Sat Dec 16 11:45:12 GMT 2023
|
||
|
DEA NO. |
9822
Created by
admin on Sat Dec 16 11:45:12 GMT 2023 , Edited by admin on Sat Dec 16 11:45:12 GMT 2023
|
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
1169-70-6
Created by
admin on Sat Dec 16 11:45:12 GMT 2023 , Edited by admin on Sat Dec 16 11:45:12 GMT 2023
|
PRIMARY | |||
|
621174
Created by
admin on Sat Dec 16 11:45:12 GMT 2023 , Edited by admin on Sat Dec 16 11:45:12 GMT 2023
|
PRIMARY | |||
|
BUTYRFENTANYL
Created by
admin on Sat Dec 16 11:45:12 GMT 2023 , Edited by admin on Sat Dec 16 11:45:12 GMT 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. | ||
|
100000166697
Created by
admin on Sat Dec 16 11:45:12 GMT 2023 , Edited by admin on Sat Dec 16 11:45:12 GMT 2023
|
PRIMARY | |||
|
07V1H7R6ZN
Created by
admin on Sat Dec 16 11:45:12 GMT 2023 , Edited by admin on Sat Dec 16 11:45:12 GMT 2023
|
PRIMARY | |||
|
BUTYRFENTANYL
Created by
admin on Sat Dec 16 11:45:12 GMT 2023 , Edited by admin on Sat Dec 16 11:45:12 GMT 2023
|
PRIMARY | |||
|
DTXSID30347410
Created by
admin on Sat Dec 16 11:45:12 GMT 2023 , Edited by admin on Sat Dec 16 11:45:12 GMT 2023
|
PRIMARY | |||
|
DB09173
Created by
admin on Sat Dec 16 11:45:12 GMT 2023 , Edited by admin on Sat Dec 16 11:45:12 GMT 2023
|
PRIMARY | |||
|
SUB180956
Created by
admin on Sat Dec 16 11:45:12 GMT 2023 , Edited by admin on Sat Dec 16 11:45:12 GMT 2023
|
PRIMARY |
ACTIVE MOIETY
SALT/SOLVATE (PARENT)