Nitrazepam
7-nitro-5-phenyl-1,3-dihydro-1,4-benzodiazepin-2-one
Overview
Nitrazepam belongs to Depressants / Benzodiazepines.
Effects
- Drowsiness and sleep, muscle relaxation, calm and reduced anxiety.
- Impaired coordination, memory and concentration, and, because of the long half-life, grogginess, unsteadiness and slowed reactions the next day.
- With regular use: tolerance to the hypnotic effect, dependence, and rebound insomnia/anxiety and other withdrawal symptoms on stopping.
Dosing & duration
Oral (tablets), taken at night: prescribed and dose-adjusted by a clinician. Figures are therapeutic (prescribing) context, not a recreational guide.. Nitrazepam is a prescription hypnotic for short-term use. The long half-life means it accumulates and impairs the following day, so the lowest effective dose and the shortest course are used, with lower doses in the elderly. It should not be combined with alcohol, opioids or other sedatives, and users should not drive while affected (including the morning after).
Dose ranges
5–10 mg
2.5–5 mg
Duration
≈30–60 min (peak ~2 h)
Hypnotic effect overnight, sedation can persist into the next day
Next-day drowsiness/'hangover'. Rebound insomnia on stopping
Chemical & Physical Properties
| Formula | C15H11N3O3 |
| Molar mass | 281.27 g/mol |
| State | Solid |
| Melting point | 225 °C |
| Boiling point | Not reported |
| Density | Not reported |
| Vapor pressure | Not reported |
| pKa | Not reported |
| LogP | 2.25 |
| Solubility | 2.99×10⁻² g/L, >42.2 [µg/mL] (The mean of the results at pH 7.4) |
| Refractive index | Not reported |
Identifiers & Synonyms
| CAS | 146-22-5 |
| CAS (enantiomer) | |
| PubChem CID | 4506 |
| InChIKey | KJONHKAYOJNZEC-UHFFFAOYSA-N |
| InChI | InChI=1S/C15H11N3O3/c19-14-9-16-15(10-4-2-1-3-5-10)12-8-11(18(20)21)6-7-13(12)17-14/h1-8H,9H2,(H,17,19) |
| SMILES | C1C(=O)NC2=C(C=C(C=C2)[N+](=O)[O-])C(=N1)C3=CC=CC=C3 |
Synonyms
- Mogadon
Pharmacodynamics & Biochemistry
Nitrazepam (Mogadon) is a long-acting nitro-benzodiazepine hypnotic. Like other benzodiazepines it is a positive allosteric modulator at the benzodiazepine site of the GABA-A receptor (the α/γ2 subunit interface). It does not open the channel itself but, in the presence of GABA, increases the frequency of chloride-channel opening, enhancing inhibitory neurotransmission to produce sedation, hypnosis, anxiolysis, muscle relaxation and anticonvulsant effects. It binds that site with high (nanomolar) affinity and behaves as a full agonist there. It is well absorbed orally (peak ~2 h) and metabolised in the liver without clinically significant active metabolites, but it is eliminated slowly: half-life roughly 16–38 hours (mean ~26 h, longer in the elderly). This long half-life means the drug and its sedation carry over into the next day ('hangover' effect) and accumulate with nightly use, which is why it is now generally reserved for short-term use and used cautiously in older people.
Biological targets
- GABA-A
Binding & functional measurements
| Target | Measurement | Species |
|---|---|---|
| GABA-A α1β2γ2 receptor | EC50 52 nM | Human |
Pharmacokinetics
| Bioavailability | Not reported |
| Tmax | ≈2 h (range 0.5–5 h) |
| Half-life | ≈16–38 h (mean ≈26 h, longer in the elderly) |
| Vd | Not reported |
| Protein binding | Not reported |
| Metabolism | Hepatic, without clinically significant active metabolites |
| Excretion | Renal |
Toxicology & Safety
Not reported
Nitrazepam is a strong, long-acting hypnotic, and its long half-life is the main practical hazard: sedation, impaired coordination, memory and reaction time carry over into the next day and accumulate with nightly use, raising the risk of falls and hip fractures (especially in the elderly) and of impaired driving. Like all benzodiazepines it causes tolerance (its sleep-inducing effect can fade within about a week), physical dependence and, on stopping after regular use, a withdrawal syndrome (rebound insomnia, anxiety, tremor and, after high-dose or abrupt cessation, seizures), so courses are kept short and doses tapered. It can cause respiratory depression, which becomes dangerous when it is combined with opioids, alcohol or other CNS depressants: the usual mechanism of benzodiazepine-related death. It should be avoided or used with great caution in sleep apnoea, severe respiratory insufficiency, myasthenia gravis, severe hepatic impairment and in the elderly, and it is misused recreationally.[2]
Legal Status
US: Schedule IV. UK: Class C (Schedule 4). DE: BtMG Anlage III
Interactions & Contraindications
Drug interactions
Contraindications
No interactions or contraindications listed.
Usage & Context
- A hypnotic (sleeping tablet) for the short-term treatment of severe, disabling insomnia: taken at night. Its use has declined in favour of shorter-acting agents because of its next-day carry-over.
- An anticonvulsant used for myoclonic seizures and infantile spasms (West syndrome) in children, where it is reported to be at least as effective as clonazepam, and occasionally to ease alcohol withdrawal.
- Also misused recreationally as a sedative. It is a controlled prescription drug.
Sources & Evidence
- PubChem: Nitrazepam (CID 4506) — identifiers & experimental properties
- Wikipedia: Nitrazepam (Mogadon) — GABA-A benzodiazepine-site PAM, long half-life (16–38 h), uses (insomnia, West syndrome), adverse effects & legal status CC BY-SA 4.0
- DEA Diversion Control Division: Controlled Substance Schedules (nitrazepam is Schedule IV)
- GOV.UK: Controlled drugs list — nitrazepam is Class C / Schedule 4 (Misuse of Drugs legislation) OGL v3.0
- Norman C, Liin SI, Jauregi-Miguel A, Ottosson NE, Gréen H (2026). In vitro γ-aminobutyric acid A (GABAA) receptor activity and binding interactions at the α+/γ2− interface of 53 prescription and designer benzodiazepines. Commun Chem 9:155.
PMID 41946818 · doi:10.1038/s42004-026-02001-x