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Details

Stereochemistry RACEMIC
Molecular Formula C16H12Cl2N2O2
Molecular Weight 335.185
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LORMETAZEPAM

SMILES

CN1C2=CC=C(Cl)C=C2C(=NC(O)C1=O)C3=CC=CC=C3Cl

InChI

InChIKey=FJIKWRGCXUCUIG-UHFFFAOYSA-N
InChI=1S/C16H12Cl2N2O2/c1-20-13-7-6-9(17)8-11(13)14(19-15(21)16(20)22)10-4-2-3-5-12(10)18/h2-8,15,21H,1H3

HIDE SMILES / InChI
Molecular Formula C16H12Cl2N2O2
Molecular Weight 335.185
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/1687574 https://www.ncbi.nlm.nih.gov/pubmed/6124982

Lormetazepam (or methyl-lorazepam), possesses hypnotic, anxiolytic, sedative and skeletal muscle relaxant properties. Lormetazepam is not approved for sale in the United States or Canada, though it is licensed in the Netherlands as 1 and 2 mg tablets, under the brand names Loramet and Noctamid and as generic, available from several different manufacturers. Lormetazepam is a short-acting benzodiazepine and is sometimes used in patients who have difficulty in maintaining sleep or falling asleep. Lormetazepam binds to the benzodiazepine receptor which in turn enhances the effect of the GABAA receptor producing its therapeutic effects as well as adverse effects. Lormetazepam appears to be more selective in the type of benzodiazepine receptor it binds to showing a higher affinity for the omega 1 receptor which is responsible for sedation. Changes in electroencephalography can therefore be used to measure the sedative sleep promoting properties of lormetazepam.

CNS Activity

CNS Active
4002
Curator's Comment: Lormetazepam acts through the central nervous system

Originator

Approval Year

Unknown
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
Binding Agent
1076
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Approved
8583
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
27.2 ng/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/1974495/
0.03 mg/kg single, oral
dose: 0.03 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
LORMETAZEPAM plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
13.9 ng/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/1974495/
0.03 mg/kg single, oral
dose: 0.03 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
LORMETAZEPAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
167 ng × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/1974495/
0.03 mg/kg single, oral
dose: 0.03 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
LORMETAZEPAM plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
64 ng × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/1974495/
0.015 mg/kg single, intravenous
dose: 0.015 mg/kg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
LORMETAZEPAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
85 ng × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/1974495/
0.015 mg/kg single, intravenous
dose: 0.015 mg/kg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
LORMETAZEPAM plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
84 ng × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/1974495/
0.03 mg/kg single, oral
dose: 0.03 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
LORMETAZEPAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
13.1 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/43806/
2 mg single, oral
dose: 2 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
LORMETAZEPAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FED
13.3 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/43806/
0.2 mg single, intravenous
dose: 0.2 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
LORMETAZEPAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
0.2 mg single, intravenous
Studied dose
Dose: 0.2 mg
Route: intravenous
Route: single
Dose: 0.2 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/43806/
healthy
Health Status: healthy
Sex: M
Food Status: FED
Sources:
https://pubmed.ncbi.nlm.nih.gov/43806/
Sources:
https://pubmed.ncbi.nlm.nih.gov/43806/
2 mg single, oral
Studied dose
Dose: 2 mg
Route: oral
Route: single
Dose: 2 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/43806/
healthy
Health Status: healthy
Sex: M
Food Status: FED
Sources:
https://pubmed.ncbi.nlm.nih.gov/43806/
Sources:
https://pubmed.ncbi.nlm.nih.gov/43806/
PubMed

PubMed

TitleDatePubMed
Analysis of six benzodiazepines in vitreous humor by high-performance liquid chromatography-photodiode-array detection.
2010-11
Development and validation of an EI-GC-MS method for the determination of benzodiazepine drugs and their metabolites in blood: applications in clinical and forensic toxicology.
2010-08-01
A validated method for simultaneous screening and quantification of twenty-three benzodiazepines and metabolites plus zopiclone and zaleplone in whole blood by liquid-liquid extraction and ultra-performance liquid chromatography- tandem mass spectrometry.
2010-07-29
The impact of perfectionism and anxiety traits on action monitoring in major depressive disorder.
2010-07
Experimental design for optimization of microwave-assisted extraction of benzodiazepines in human plasma.
2010-05
A comparison of theoretical methods of calculation of partition coefficients for selected drugs.
2010-01-21
Conversion visual loss: a differential diagnosis in infant amblyopia.
2009-11-03
Benzodiazepine prescription and length of hospital stay at a Japanese university hospital.
2009-10-09
Psychoactive medication and traffic safety.
2009-03
Clinical review: The impact of noise on patients' sleep and the effectiveness of noise reduction strategies in intensive care units.
2009
[Paroxetine-induced severe hyponatremic rhabdomyolisis].
2008-10
Use of computerized dynamic posturography to assess balance in older adults after nighttime awakenings using zolpidem as a reference.
2008-07-15
Evaluation of anxiolytic-like effects of some short-acting benzodiazepine hypnotics in mice.
2008-07
Decrease in tobacco consumption after treatment with topiramate and aripiprazole: a case report.
2008-06-11
GABA(A) receptors in normal development and seizures: friends or foes?
2008-03
Sleep disturbances and depression: risk relationships for subsequent depression and therapeutic implications.
2008
How useful are prescribing indicators based on the DU90% method to distinguish the quality of prescribing between pharmacotherapy audit meetings with different levels of functioning?
2007-12
Eszopiclone: its use in the treatment of insomnia.
2007-08
Quantification of lorazepam and lormetazepam in human breast milk using GC-MS in the negative chemical ionization mode.
2007-05
Role of lormetazepam in the treatment of insomnia in the elderly.
2007
Quantification of benzodiazepines in whole blood and serum.
2006-11
Abusive prescription of psychostimulants: a study of two cases.
2006-03
Screening method for benzodiazepines and hypnotics in hair at pg/mg level by liquid chromatography-mass spectrometry/mass spectrometry.
2005-10-15
Next-day residual effects of hypnotics in DSM-IV primary insomnia: a driving simulator study with simultaneous electroencephalogram monitoring.
2005-10
Screening and confirmatory method for benzodiazepines and hypnotics in oral fluid by LC-MS/MS.
2005-06-10
[Benzodiazepine and hiccup: three case reports].
2005-06-03
Psychomotor performance in healthy young adult volunteers receiving lormetazepam and placebo: a single-dose, randomized, double-blind, crossover trial.
2005-01
Lormetazepam in depressive insomnia: new evidence of phase-response effects of benzodiazepines.
2004-09
[The use of anxiolytic and hypnotic drugs in Spain (1995-2002)].
2004-08-06
Screening, library-assisted identification and validated quantification of 23 benzodiazepines, flumazenil, zaleplone, zolpidem and zopiclone in plasma by liquid chromatography/mass spectrometry with atmospheric pressure chemical ionization.
2004-08
Comparative efficacy of newer hypnotic drugs for the short-term management of insomnia: a systematic review and meta-analysis.
2004-07
A randomized clinical trial comparing doses and efficacy of lormetazepam tablets or oral solution for insomnia in a general practice setting.
2004-03
Residual effects of hypnotics: epidemiology and clinical implications.
2004
The use of hypnosedative drugs in a university hospital setting.
2003-11-26
Effects on postural oscillation and memory functions of a single dose of zolpidem 5 mg, zopiclone 3.75 mg and lormetazepam 1 mg in elderly healthy subjects. A randomized, cross-over, double-blind study versus placebo.
2003-07
Effects of short-acting hypnotics on sleep latency in rats placed on grid suspended over water.
2003-01-24
Musical hallucinations during a treatment with benzodiazepine.
2002-10
Trimipramine in primary insomnia: results of a polysomnographic double-blind controlled study.
2002-09
Lormetazepam effects on daytime vigilance, psychomotor performance and simulated driving in young adult healthy volunteers.
2002-07
Determination of lormetazepam and its main metabolite in serum using micellar electrokinetic capillary chromatography with direct injection and ultraviolet absorbance detection.
2002-06-25
Immobilized halogenophenylcarbamate derivatives of cellulose as novel stationary phases for enantioselective drug analysis.
2002-01-15
Fast withdrawal from benzodiazepines in geriatric inpatients: a randomised double-blind, placebo-controlled trial.
2002-01
Simultaneous determination of fifteen low-dosed benzodiazepines in human urine by solid-phase extraction and gas chromatography-mass spectrometry.
2001-12-25
Adsorption of xenobiotics to plastic tubing incorporated into dynamic in vitro systems used in pharmacological research--limits and progress.
2001-07
[Instead of benzodiazepines. An antidepressant as sleep aid].
2001-01-18
Patents

Patents

JP2012500248A
3

Sample Use Guides

In Vivo Use Guide
1 tablet Noctamid (lormetazepam) (1 mg) as a single dose. Elderly and debilitated patients take half a tablet (0,5 mg).
Route of Administration: Oral
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Mon Mar 31 17:57:41 GMT 2025
Edited
by admin
on Mon Mar 31 17:57:41 GMT 2025
Record UNII
GU56C842ZA
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LORMETAZEPAM
INN   JAN   MART.   MI   USAN   WHO-DD  
USAN   INN  
Official Name English
LORAMET
Preferred Name English
LORMETAZEPAM [USAN]
Common Name English
7-Chloro-5-(O-chlorophenyl)-1,3-dihydro-3-hydroxy-1-methyl-2H-1,4-benzodiazepin-2-one
Common Name English
LORMETAZEPAM [MART.]
Common Name English
2H-1,4-BENZODIAZEPIN-2-ONE, 7-CHLORO-5-(2-CHLOROPHENYL)-1,3-DIHYDRO-3-HYDROXY-1-METHYL-
Systematic Name English
Lormetazepam [WHO-DD]
Common Name English
7-CHLORO-5-(2-CHLOROPHENYL)-1,3-DIHYDRO-3-HYDROXY-1-METHYL-2H-1,4-BENZODIAZEPIN-2-ONE
Systematic Name English
LORMETAZEPAM [MI]
Common Name English
WY-4082
Code English
LORMETAZEPAM [JAN]
Common Name English
lormetazepam [INN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C1012
Created by admin on Mon Mar 31 17:57:41 GMT 2025 , Edited by admin on Mon Mar 31 17:57:41 GMT 2025
WHO-ATC N05CD06
Created by admin on Mon Mar 31 17:57:41 GMT 2025 , Edited by admin on Mon Mar 31 17:57:41 GMT 2025
DEA NO. 2774
Created by admin on Mon Mar 31 17:57:41 GMT 2025 , Edited by admin on Mon Mar 31 17:57:41 GMT 2025
WHO-VATC QN05CD06
Created by admin on Mon Mar 31 17:57:41 GMT 2025 , Edited by admin on Mon Mar 31 17:57:41 GMT 2025
Code System Code Type Description
ChEMBL
CHEMBL22097
Created by admin on Mon Mar 31 17:57:41 GMT 2025 , Edited by admin on Mon Mar 31 17:57:41 GMT 2025
PRIMARY
MESH
C023842
Created by admin on Mon Mar 31 17:57:41 GMT 2025 , Edited by admin on Mon Mar 31 17:57:41 GMT 2025
PRIMARY
MERCK INDEX
m6909
Created by admin on Mon Mar 31 17:57:41 GMT 2025 , Edited by admin on Mon Mar 31 17:57:41 GMT 2025
PRIMARY Merck Index
EPA CompTox
DTXSID40862442
Created by admin on Mon Mar 31 17:57:41 GMT 2025 , Edited by admin on Mon Mar 31 17:57:41 GMT 2025
PRIMARY
ECHA (EC/EINECS)
212-700-5
Created by admin on Mon Mar 31 17:57:41 GMT 2025 , Edited by admin on Mon Mar 31 17:57:41 GMT 2025
PRIMARY
CAS
848-75-9
Created by admin on Mon Mar 31 17:57:41 GMT 2025 , Edited by admin on Mon Mar 31 17:57:41 GMT 2025
PRIMARY
CHEBI
52993
Created by admin on Mon Mar 31 17:57:41 GMT 2025 , Edited by admin on Mon Mar 31 17:57:41 GMT 2025
PRIMARY
WIKIPEDIA
LORMETAZEPAM
Created by admin on Mon Mar 31 17:57:41 GMT 2025 , Edited by admin on Mon Mar 31 17:57:41 GMT 2025
PRIMARY
PUBCHEM
13314
Created by admin on Mon Mar 31 17:57:41 GMT 2025 , Edited by admin on Mon Mar 31 17:57:41 GMT 2025
PRIMARY
FDA UNII
GU56C842ZA
Created by admin on Mon Mar 31 17:57:41 GMT 2025 , Edited by admin on Mon Mar 31 17:57:41 GMT 2025
PRIMARY
INN
4339
Created by admin on Mon Mar 31 17:57:41 GMT 2025 , Edited by admin on Mon Mar 31 17:57:41 GMT 2025
PRIMARY
EVMPD
SUB08588MIG
Created by admin on Mon Mar 31 17:57:41 GMT 2025 , Edited by admin on Mon Mar 31 17:57:41 GMT 2025
PRIMARY
DRUG BANK
DB13872
Created by admin on Mon Mar 31 17:57:41 GMT 2025 , Edited by admin on Mon Mar 31 17:57:41 GMT 2025
PRIMARY
LACTMED
Lormetazepam
Created by admin on Mon Mar 31 17:57:41 GMT 2025 , Edited by admin on Mon Mar 31 17:57:41 GMT 2025
PRIMARY
RXCUI
28894
Created by admin on Mon Mar 31 17:57:41 GMT 2025 , Edited by admin on Mon Mar 31 17:57:41 GMT 2025
PRIMARY RxNorm
SMS_ID
100000091985
Created by admin on Mon Mar 31 17:57:41 GMT 2025 , Edited by admin on Mon Mar 31 17:57:41 GMT 2025
PRIMARY
NCI_THESAURUS
C87673
Created by admin on Mon Mar 31 17:57:41 GMT 2025 , Edited by admin on Mon Mar 31 17:57:41 GMT 2025
PRIMARY
DRUG CENTRAL
1608
Created by admin on Mon Mar 31 17:57:41 GMT 2025 , Edited by admin on Mon Mar 31 17:57:41 GMT 2025
PRIMARY
Related Record Type Details
Structure of 2-CHLORODIAZEPAM
PARENT -> METABOLITE
URINE
Related Record Type Details
Structure of LORMETAZEPAM
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