Identification

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Name
Butyrfentanyl
Accession Number
DB09173
Type
Small Molecule
Groups
Illicit
Description

Butyrfentanyl or butyrylfentanyl (not to be confused with 3-methylfentanyl) is a potent short-acting synthetic opioid analgesic drug.1 It is an analog of fentanyl with roughly 1/30 the potency.6 Butyrfentanyl was first synthesized in 1961 by Janssen Pharmaceuticals as a new opioid analgesic.6

Butyrfentanyl has no current legitimate clinical applications, but anecdotal reports indicate it may occasionally be surfacing on the grey-market as a recreational drug.6 This compound is a schedule I controlled substance in the USA because it is a positional isomer of 3-Methylfentanyl.7

The DEA in the United States has confirmed at least 40 fatalities involving butyrfentanyl before May 2016.6

Structure
Thumb
Synonyms
  • Butyr-fentanyl
  • Butyrylfentanyl
External IDs
NIH-10486 FREE BASE
Categories
UNII
07V1H7R6ZN
CAS number
1169-70-6
Weight
Average: 350.506
Monoisotopic: 350.235813594
Chemical Formula
C23H30N2O
InChI Key
QQOMYEQLWQJRKK-UHFFFAOYSA-N
InChI
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
IUPAC Name
N-phenyl-N-[1-(2-phenylethyl)piperidin-4-yl]butanamide
SMILES
CCCC(=O)N(C1CCN(CCC2=CC=CC=C2)CC1)C1=CC=CC=C1

Pharmacology

Indication

Butyrfentanyl was investigated as a potential opioid analgesic but is no longer used for this purpose.2 It is more often being used as a recreational drug.2

Pharmacodynamics

Data for the pharmacodynamics of butyrfentanyl are not readily available.

Mechanism of action

Butyrfentanyl is a µ opioid receptor agonist similar to fentanyl.6

TargetActionsOrganism
AMu-type opioid receptor
agonist
Humans
UKappa-type opioid receptor
agonist
Humans
UDelta-type opioid receptor
agonist
Humans
Absorption

Data for the absorption of butyrfentanyl are not readily available.

Volume of distribution

Data for the volume of distribution of butyrfentanyl are not readily available.

Protein binding

Protein binding studies for butyrfentanyl have not been performed but due to its structural similarity with fentanyl it is likely highly bound to serum albumin and alpha-1-acid glycoprotein in circulation.5

Metabolism

Butyrfentanyl can be N-dealkylated to nor-butyrfentanyl by CYP3A4 and CYP2D6, hydroxylated to (ω-1)-hydroxy-butyrfentanyl by CYP3A4, 4'-hydroxylated to 4'-hydroxy-butyrfentanyl, hydroxylated to ω-hydroxy-butyrfentanyl bye CYP2D6 or CYP3A4, or hydroxylated to β-hydroxy-butyrfentanyl by CYP3A4.1 ω-hydroxy-butyrfentanyl is further metabolized to ω-carboxy-butyrfentanyl while 4'-hydroxy-butyrfentanyl is further metabolized to 4'-hydroxy-3'-methoxy-butyrfentanyl.1 Many of these metabolites may undergo further conjugation reactions with glucuronic acid or sulfate.1

Route of elimination

The route of elimination of butyrfentanyl has not been well described in the literature but most opioids are mainly eliminated in the urine.3

Half life

Data for the half life of butyrfentanyl are not readily available.

Clearance

Data for the clearance of butyrfentanyl are not readily available.

Toxicity

The LD50 of butyrfentanyl is not readily available.8

Patients experiencing an overdose may present with sedation, altered mental state, and difficulty breathing.4 Symptoms of overdose may be treated with naloxone and supportive measures.4

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
1-(2-Phenylethyl)-4-phenyl-4-acetoxypiperidineThe metabolism of Butyrfentanyl can be decreased when combined with 1-(2-Phenylethyl)-4-phenyl-4-acetoxypiperidine.
4-MethoxyamphetamineThe metabolism of Butyrfentanyl can be decreased when combined with 4-Methoxyamphetamine.
5-methoxy-N,N-dimethyltryptamineThe metabolism of 5-methoxy-N,N-dimethyltryptamine can be decreased when combined with Butyrfentanyl.
AbataceptThe metabolism of Butyrfentanyl can be increased when combined with Abatacept.
AbirateroneThe metabolism of Butyrfentanyl can be decreased when combined with Abiraterone.
AcebutololThe metabolism of Butyrfentanyl can be decreased when combined with Acebutolol.
AcetaminophenThe metabolism of Butyrfentanyl can be decreased when combined with Acetaminophen.
AdalimumabThe metabolism of Butyrfentanyl can be increased when combined with Adalimumab.
AfelimomabThe metabolism of Butyrfentanyl can be increased when combined with Afelimomab.
AlmotriptanThe metabolism of Butyrfentanyl can be decreased when combined with Almotriptan.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

    Learn more
  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
Not Available

References

Synthesis Reference

Janssen PAJ. 1-Aralkyl-4-(N-aryl-carbonyl amino)piperidines and related compounds. US Patent No. US3164600 (January 5, 1965). 1965.

General References
  1. Kanamori T, Iwata YT, Segawa H, Yamamuro T, Kuwayama K, Tsujikawa K, Inoue H: Metabolism of Butyrylfentanyl in Fresh Human Hepatocytes: Chemical Synthesis of Authentic Metabolite Standards for Definitive Identification. Biol Pharm Bull. 2019;42(4):623-630. doi: 10.1248/bpb.b18-00765. [PubMed:30930421]
  2. Baumann MH, Majumdar S, Le Rouzic V, Hunkele A, Uprety R, Huang XP, Xu J, Roth BL, Pan YX, Pasternak GW: Pharmacological characterization of novel synthetic opioids (NSO) found in the recreational drug marketplace. Neuropharmacology. 2018 May 15;134(Pt A):101-107. doi: 10.1016/j.neuropharm.2017.08.016. Epub 2017 Aug 12. [PubMed:28807672]
  3. Smith HS: Opioid metabolism. Mayo Clin Proc. 2009 Jul;84(7):613-24. doi: 10.1016/S0025-6196(11)60750-7. [PubMed:19567715]
  4. Cole JB, Dunbar JF, McIntire SA, Regelmann WE, Slusher TM: Butyrfentanyl overdose resulting in diffuse alveolar hemorrhage. Pediatrics. 2015 Mar;135(3):e740-3. doi: 10.1542/peds.2014-2878. [PubMed:25713275]
  5. Bista SR, Haywood A, Hardy J, Lobb M, Tapuni A, Norris R: Protein binding of fentanyl and its metabolite nor-fentanyl in human plasma, albumin and alpha-1 acid glycoprotein. Xenobiotica. 2015 Mar;45(3):207-12. doi: 10.3109/00498254.2014.971093. Epub 2014 Oct 14. [PubMed:25314012]
  6. World Health Organization: Butyrfentanyl Critical Review Report [Link]
  7. DEA: Temporary Placement of Butyryl Fentanyl and Beta-Hydroxythiofentanyl Into Schedule I [Link]
  8. Cayman Chemicals: Butyrylfentanyl MSDS [Link]
External Links
PubChem Compound
621174
PubChem Substance
310265082
ChemSpider
539764
Wikipedia
Butyrfentanyl

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0137 mg/mLALOGPS
logP4.44ALOGPS
logP4.26ChemAxon
logS-4.4ALOGPS
pKa (Strongest Basic)8.77ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area23.55 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity108.08 m3·mol-1ChemAxon
Polarizability42.03 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as fentanyls. These are compounds containing the fentanyl moiety or a derivative, which is based on a N-(1-(2-phenylethyl)-4-piperidinyl)-N-phenylpropanamide skeleton.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Piperidines
Sub Class
Fentanyls
Direct Parent
Fentanyls
Alternative Parents
Phenethylamines / Anilides / Aralkylamines / Tertiary carboxylic acid amides / Trialkylamines / Amino acids and derivatives / Azacyclic compounds / Organopnictogen compounds / Organic oxides / Hydrocarbon derivatives
show 1 more
Substituents
Fentanyl / Phenethylamine / Anilide / Aralkylamine / Monocyclic benzene moiety / Benzenoid / Tertiary carboxylic acid amide / Amino acid or derivatives / Carboxamide group / Tertiary amine
show 13 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Agonist
General Function
Voltage-gated calcium channel activity
Specific Function
Receptor for endogenous opioids such as beta-endorphin and endomorphin. Receptor for natural and synthetic opioids including morphine, heroin, DAMGO, fentanyl, etorphine, buprenorphin and methadone...
Gene Name
OPRM1
Uniprot ID
P35372
Uniprot Name
Mu-type opioid receptor
Molecular Weight
44778.855 Da
References
  1. Baumann MH, Majumdar S, Le Rouzic V, Hunkele A, Uprety R, Huang XP, Xu J, Roth BL, Pan YX, Pasternak GW: Pharmacological characterization of novel synthetic opioids (NSO) found in the recreational drug marketplace. Neuropharmacology. 2018 May 15;134(Pt A):101-107. doi: 10.1016/j.neuropharm.2017.08.016. Epub 2017 Aug 12. [PubMed:28807672]
  2. World Health Organization: Butyrfentanyl Critical Review Report [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Agonist
General Function
Opioid receptor activity
Specific Function
G-protein coupled opioid receptor that functions as receptor for endogenous alpha-neoendorphins and dynorphins, but has low affinity for beta-endorphins. Also functions as receptor for various synt...
Gene Name
OPRK1
Uniprot ID
P41145
Uniprot Name
Kappa-type opioid receptor
Molecular Weight
42644.665 Da
References
  1. Baumann MH, Majumdar S, Le Rouzic V, Hunkele A, Uprety R, Huang XP, Xu J, Roth BL, Pan YX, Pasternak GW: Pharmacological characterization of novel synthetic opioids (NSO) found in the recreational drug marketplace. Neuropharmacology. 2018 May 15;134(Pt A):101-107. doi: 10.1016/j.neuropharm.2017.08.016. Epub 2017 Aug 12. [PubMed:28807672]
  2. World Health Organization: Butyrfentanyl Critical Review Report [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Agonist
General Function
Opioid receptor activity
Specific Function
G-protein coupled receptor that functions as receptor for endogenous enkephalins and for a subset of other opioids. Ligand binding causes a conformation change that triggers signaling via guanine n...
Gene Name
OPRD1
Uniprot ID
P41143
Uniprot Name
Delta-type opioid receptor
Molecular Weight
40368.235 Da
References
  1. Baumann MH, Majumdar S, Le Rouzic V, Hunkele A, Uprety R, Huang XP, Xu J, Roth BL, Pan YX, Pasternak GW: Pharmacological characterization of novel synthetic opioids (NSO) found in the recreational drug marketplace. Neuropharmacology. 2018 May 15;134(Pt A):101-107. doi: 10.1016/j.neuropharm.2017.08.016. Epub 2017 Aug 12. [PubMed:28807672]
  2. World Health Organization: Butyrfentanyl Critical Review Report [Link]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Kanamori T, Iwata YT, Segawa H, Yamamuro T, Kuwayama K, Tsujikawa K, Inoue H: Metabolism of Butyrylfentanyl in Fresh Human Hepatocytes: Chemical Synthesis of Authentic Metabolite Standards for Definitive Identification. Biol Pharm Bull. 2019;42(4):623-630. doi: 10.1248/bpb.b18-00765. [PubMed:30930421]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
Molecular Weight
55768.94 Da
References
  1. Kanamori T, Iwata YT, Segawa H, Yamamuro T, Kuwayama K, Tsujikawa K, Inoue H: Metabolism of Butyrylfentanyl in Fresh Human Hepatocytes: Chemical Synthesis of Authentic Metabolite Standards for Definitive Identification. Biol Pharm Bull. 2019;42(4):623-630. doi: 10.1248/bpb.b18-00765. [PubMed:30930421]

Drug created on October 14, 2015 14:53 / Updated on September 02, 2019 19:07