Phenibut
4-amino-3-phenylbutanoic acid
Overview
Phenibut belongs to Depressants.
Effects
- Anxiolysis, relaxation, sociability, mild euphoria and improved sleep are the sought-after effects. At higher doses, sedation, disinhibition and an alcohol- or baclofen-like intoxication.
- The slow onset (often 2–4 hours) frequently leads users to redose prematurely, escalating the total dose and the risk of over-sedation.
- Tolerance develops rapidly and regular use leads to dependence. Acute overdose, usually in combination with other depressants, causes marked sedation, reduced consciousness and sometimes agitation or delirium.
Dosing & duration
Oral (powder or capsules, usually the hydrochloride salt). Occasionally rectal.. The figures below are commonly cited reference ranges, not a recommendation or a 'safe' dose. Two features make phenibut particularly risky: its onset is slow (2–4 hours), which tempts premature redosing and accidental overdose, and it produces rapid tolerance and a severe physical dependence with a dangerous withdrawal syndrome (rebound anxiety, insomnia, agitation, tremor and, in some cases, hallucinations, psychosis or seizures). Combining phenibut with alcohol, benzodiazepines, opioids or other CNS depressants adds sedation and respiratory-depression risk. Do not use daily. After regular use, taper rather than stopping abruptly.
Dose ranges
0.25 g
0.5–1 g
1–2 g
2–3.5 g
3.5 g +
Duration
1.5–4 hours (slow)
10–24 hours
6–24 hours. Rapid tolerance, and with regular use dependence and a severe withdrawal syndrome
Chemical & Physical Properties
| Formula | C10H13NO2 |
| Molar mass | 179.22 g/mol |
| State | Solid (usually the hydrochloride salt, white crystalline powder, zwitterionic amino acid) |
| Melting point | ≈253 °C (hydrochloride) |
| Boiling point | Not reported |
| Density | Not reported |
| Vapor pressure | Not reported |
| pKa | Not reported |
| LogP | -1.6 (predicted, XLogP3, free base) |
| Solubility | Not reported |
| Refractive index | Not reported |
Identifiers & Synonyms
| CAS | 1078-21-3 |
| CAS (enantiomer) | |
| PubChem CID | 14113 |
| InChIKey | DAFOCGYVTAOKAJ-UHFFFAOYSA-N |
| InChI | InChI=1S/C10H13NO2/c11-7-9(6-10(12)13)8-4-2-1-3-5-8/h1-5,9H,6-7,11H2,(H,12,13) |
| SMILES | C1=CC=C(C=C1)C(CC(=O)O)CN |
Synonyms
- Anvifen
- Noofen
- Fenibut
- β-phenyl-GABA
Pharmacodynamics & Biochemistry
Phenibut (β-phenyl-GABA) is a phenylated analogue of the neurotransmitter GABA, developed in the Soviet Union in the 1960s and used there as an anxiolytic and nootropic. Its clinically relevant activity resides almost entirely in the R-enantiomer. Its principal mechanism is agonism at GABA-B receptors, acting as a weaker, longer-acting relative of baclofen, which produces its anxiolytic, sedative and muscle-relaxant effects. The S-enantiomer does not bind GABA-B. Additional GABA-A and dopaminergic effects have been reported at higher doses. Phenibut also behaves as a gabapentinoid: R-phenibut binds the α2δ subunit of voltage-dependent calcium channels: in rat-brain membranes with an affinity (Ki ≈ 23 µM) about four times higher than its affinity for the GABA-B receptor, which contributes gabapentin-like anti-nociceptive effects. Both affinities are weak (micromolar), which is why gram-range doses are needed for an effect. Its pharmacokinetics shape its use pattern and risks: a slow oral onset (2–4 hours), a long duration (up to about 24 hours), minimal metabolism and largely unchanged renal excretion.
Biological targets
- GABA-B
- VGCC α2δ
Binding & functional measurements
Pharmacokinetics
| Bioavailability | Oral ≥63% (250 mg dose) |
| Tmax | Not reported |
| Half-life | ≈5.3 h (250 mg) |
| Vd | Not reported |
| Protein binding | Not reported |
| Metabolism | Minimal hepatic metabolism |
| Excretion | Renal, ~63% excreted unchanged in urine |
Toxicology & Safety
Not reported
Phenibut is widely sold online as a 'nootropic' or calming supplement, but it carries a serious risk of tolerance, dependence and a severe withdrawal syndrome that can include rebound anxiety, insomnia, agitation, tremor, hallucinations and, in some reports, psychosis or seizures: withdrawal has required hospital management. Its slow onset (2–4 hours) encourages premature redosing and accidental overdose. Acute toxicity, usually in combination with alcohol or other depressants, presents as heavy sedation, reduced consciousness and sometimes agitation or delirium. It should not be used daily, and after regular use it must be tapered rather than stopped suddenly. It is an unapproved drug in most Western countries and is banned outright in Australia.[3][2][6]
Legal Status
US: Unapproved / unscheduled. UK: PSA 2016 (supply banned). DE: Not a medicine (grey area)
Interactions & Contraindications
Drug interactions
Contraindications
No interactions or contraindications listed.
Usage & Context
- A prescription anxiolytic and nootropic in Russia and some post-Soviet states (as Noofen, Anvifen and Fenibut) for anxiety, insomnia, tension and related conditions. It is not an approved medicine in most Western countries.
- Widely sold online as a grey-market 'nootropic' or relaxation supplement and used recreationally for its anxiolytic, mildly euphoric, alcohol-like effects: a pattern strongly associated with tolerance, dependence and a difficult withdrawal.
Sources & Evidence
- PubChem: Phenibut (CID 14113) — identifiers & computed properties
- Lapin I (2001). Phenibut (beta-phenyl-GABA): a tranquilizer and nootropic drug. CNS Drug Rev 7:471-81.
PMID 11830761 · doi:10.1111/j.1527-3458.2001.tb00211.x
- Owen DR, Wood DM, Archer JR, et al. (2016). Phenibut (4-amino-3-phenyl-butyric acid): Availability, prevalence of use, desired effects and acute toxicity. Drug Alcohol Rev 35:591-6.
PMID 26693960 · doi:10.1111/dar.12356
- Zvejniece L, Vavers E, Svalbe B, et al. (2015). R-phenibut binds to the α2-δ subunit of voltage-dependent calcium channels and exerts gabapentin-like anti-nociceptive effects. Pharmacol Biochem Behav 137:23-9.
PMID 26234470 · doi:10.1016/j.pbb.2015.07.014
- PsychonautWiki: Phenibut — recreational dosage & duration CC BY-SA 4.0
- Wikipedia: Phenibut (pharmacokinetics, legal status, chemistry) CC BY-SA 4.0