Structure via PubChem · Public domain (PubChem)
phenibut
Sign in to saveAlso known as 4-amino-3-phenylbutyric acid, aminophenylbutyric acid, β-phenyl-γ-aminobutyric acid, β-phenyl-GABA, PhGABA, PHG, phenylgamma
Phenibut, sold under the brand name Anvifen among others, is a central nervous system (CNS) depressant with anxiolytic effects, and is used to treat anxiety, insomnia, and for a variety of other indications. It is usually taken orally (swallowed by mouth), but may be given intravenously.
Key facts
- Drug.Verifiedfields
- verified
- Drug.Watchedfields
- verified
- Drug.verifiedrevid
- 464373947
- Drug.IUPAC_name
- 4-Amino-3-phenylbutanoic acid
- Drug.image
- Phenibut skeletal formula.svg
- Drug.image_class
- skin-invert-image
- Drug.width
- 200px
- Drug.image2
- Phenibut ball-and-stick model.png
- Drug.image_class2
- bg-transparent
- Drug.width2
- 200px
- Drug.tradename
- Anvifen, Fenibut, Noofen, others
- Drug.legal_AU
- S9
- Drug.legal_CA
- Unscheduled
- Drug.legal_DE
- NPSG
- Drug.legal_US
- Unapproved drug; use in dietary supplements, food, or medicine is unlawful.
- Drug.legal_UN
- Unscheduled
- Drug.legal_status
- RU: Rx-only
- Drug.routes_of_administration
- Common: OralUncommon: Rectal
via Wikipedia infobox
Chemical data
- Formula
- C10H13NO2
- Molecular weight
- 179.22 g/mol
- IUPAC name
- 4-azaniumyl-3-phenylbutanoate
- SMILES
- C1=CC=C(C=C1)C(CC(=O)[O-])C[NH3+]
- InChIKey
- DAFOCGYVTAOKAJ-UHFFFAOYSA-N
- XLogP
- -0.9
- Polar surface area
- 67.8 Ų
- H-bond donors
- 1
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Research
295 papers- Phenibut: A drug with one too many "buts".Basic & clinical pharmacology & toxicology · 2024
- Phenibut: Review and Pharmacologic Approaches to Treating Withdrawal.Journal of clinical pharmacology · 2024
- A Systematic Review of Phenibut Withdrawals.Cureus · 2024
- Clinical Presentations and Treatment of Phenibut Toxicity and Withdrawal: A Systematic Literature Review.Journal of addiction medicine · 2023
- Phenibut (β-Phenyl-γ-Aminobutyric Acid): an Easily Obtainable "Dietary Supplement" With Propensities for Physical Dependence and Addiction.Current psychiatry reports · 2019
via PubMed
Wikidata facts
- Mass
- 179.095
Show 3 more facts
- chemical formula
- C₁₀H₁₃NO₂
- canonical SMILES
- C1=CC=C(C=C1)C(CC(=O)O)CN
- Commons category
- Phenibut
via Wikidata · CC0
~13 min read
Article
22 sectionsContents
- Medical uses
- Available forms
- Contraindications
- Side effects
- Dependence and withdrawal
- Overdose
- Interactions
- Pharmacology
- Pharmacodynamics
- Pharmacokinetics
- Chemistry
- Structure and analogues
- Synthesis
- History
- Society and culture
- Other names
- Brand names
- Availability
- Recreational use
- Legal status
- See also
- References
Phenibut, sold under the brand name Anvifen among others, is a central nervous system (CNS) depressant with anxiolytic effects, and is used to treat anxiety, insomnia, and for a variety of other indications. It is usually taken orally (swallowed by mouth), but may be given intravenously.
Side effects of phenibut can include sedation, sleepiness, nausea, irritability, agitation, dizziness, euphoria, and sometimes headache, among others. Overdose of phenibut can produce marked central nervous system depression including unconsciousness. The medication is structurally related to the neurotransmitter γ-aminobutyric acid (GABA), and hence is a GABA analogue. Phenibut is thought to act as a GABAB receptor agonist, similarly to baclofen and γ-hydroxybutyrate (GHB). However, at low concentrations, phenibut mildly increases the concentration of dopamine in the brain, providing stimulatory effects in addition to the anxiolysis.