Tetrazepam (CHEM003547)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (18)XML
Record Information
Version1.0
Creation Date2014-09-05 17:11:23 UTC
Update Date2016-11-09 01:09:10 UTC
Accession NumberCHEM003547
Identification
Common NameTetrazepam
ClassSmall Molecule
DescriptionAllergic reactions can develop to tetrazepam and it is considered to be a potential allergen. Drug rash and drug-induced eosinophilia with systemic symptoms is a known complication of tetrazepam exposure. These hypersensitive allergic reactions can be of the delayed type. Drowsiness is a common side effect of tetrazepam. A reduction in muscle force can occur. Myasthenia gravis, a condition characterised by severe muscle weakness is another potential adverse effect from tetrazepam. Cardiovascular and respiratory adverse effects can occur with tetrazepam similar to other benzodiazepines. Prolonged use, as with all benzodiazepines, should be avoided, as tolerance occurs and there is a risk of benzodiazepine dependence and a benzodiazepine withdrawal syndrome after stopping or reducing dosage. Tetrazepam (is marketed under the following brand names, Clinoxan, Epsipam, Myolastan, Musaril, Relaxam and Spasmorelax) is a benzodiazepine derivative with anticonvulsant, anxiolytic, hypnotic and muscle relaxant properties. It is used mainly in Austria, France, Belgium, Germany and Spain to treat muscle spasm, anxiety disorders such as panic attacks, or more rarely to treat depression, premenstrual syndrome or agoraphobia. Tetrazepam has relatively little sedative effect at low doses while still producing useful muscle relaxation and anxiety relief. Tetrazepam is an unusual benzodiazepine in its molecular structure as it has cyclohexenyl group which has substituted the typical 5-phenyl moiety seen in other benzodiazepines. Tetrazepam, is rapidly absorbed after oral administration, within 45 mins and reaches peak plasma levels in less than 2 hours. It is classed as an intermediate acting benzodiazepine with an elimination half-life of approximately 15 hours. It is primarily metabolised to the inactive metabolites 3-hydroxy-tetrazepam and norhydroxytetrazepam. The pharmacological effects of tetrazepam are significantly less potent when compared against diazepam, in animal studies. Tetrazepam is a benzodiazepine site agonist and binds unselectively to type 1 and type 2 benzodiazepine site types as well as to peripheral benzodiazepine receptors. The muscle relaxant properties of tetrazepam are most likely due to a reduction of calcium influx. Small amounts of diazepam as well as the active metabolites of diazepam are produced from metabolism of tetrazepam. The metabolism of tetrazepam has led to false accusations of prisoners prescribed tetrazepam of taking illicit diazepam; this can lead to increased prison sentences for prisoners. Tetrazepam, like other benzodiazepines is a drug which is very frequently used in overdoses. These overdoses are often mixed overdoses, i.e. a mixture of other benzodiazepines or other drug classes with tetrazepam.
Contaminant Sources
  • STOFF IDENT Compounds
  • T3DB toxins
Contaminant Type
  • Amide
  • Amine
  • Drug
  • Metabolite
  • Organic Compound
  • Organochloride
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
MyolastanKegg
ClinoxanHMDB
MusarilHMDB
Lichtenstein brand OF tetrazepamHMDB
MobifortonHMDB
MusapamHMDB
TetramduraHMDB
Tetrazep 1a pharmaHMDB
1a Brand OF tetrazepamHMDB
AbZ brand OF tetrazepamHMDB
Gry brand OF tetrazepamHMDB
Krewel brand OF tetrazepamHMDB
MTW-TetrazepamHMDB
PanosHMDB
Tetra-saarHMDB
MTW Brand OF tetrazepamHMDB
Merck dura brand OF tetrazepamHMDB
Sanofi synthelabo brand OF tetrazepamHMDB
TethexalHMDB
TetrarelaxHMDB
Tetrazep abzHMDB
Mibe brand OF tetrazepamHMDB
Fornet brand OF tetrazepamHMDB
Hexal brand OF tetrazepamHMDB
MIP brand OF tetrazepamHMDB
MyospasmalHMDB
RilexHMDB
TAD brand OF tetrazepamHMDB
CT-Arzneimittel brand OF tetrazepamHMDB
Tetrazep von CTHMDB
Chemical FormulaC16H17ClN2O
Average Molecular Mass288.772 g/mol
Monoisotopic Mass288.103 g/mol
CAS Registry Number10379-14-3
IUPAC Name7-chloro-5-(cyclohex-1-en-1-yl)-1-methyl-2,3-dihydro-1H-1,4-benzodiazepin-2-one
Traditional Nametetrazepam
SMILESCN1C2=C(C=C(Cl)C=C2)C(=NCC1=O)C1=CCCCC1
InChI IdentifierInChI=1S/C16H17ClN2O/c1-19-14-8-7-12(17)9-13(14)16(18-10-15(19)20)11-5-3-2-4-6-11/h5,7-9H,2-4,6,10H2,1H3
InChI KeyIQWYAQCHYZHJOS-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 1,4-benzodiazepines. These are organic compounds containing a benzene ring fused to a 1,4-azepine.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzodiazepines
Sub Class1,4-benzodiazepines
Direct Parent1,4-benzodiazepines
Alternative Parents
Substituents
  • 1,4-benzodiazepine
  • Alpha-amino acid or derivatives
  • Aryl chloride
  • Aryl halide
  • Benzenoid
  • Tertiary carboxylic acid amide
  • Carboxamide group
  • Ketimine
  • Lactam
  • Carboxylic acid derivative
  • Azacycle
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Organochloride
  • Organohalogen compound
  • Hydrocarbon derivative
  • Imine
  • Organic nitrogen compound
  • Organic oxide
  • Carbonyl group
  • Organonitrogen compound
  • Organooxygen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point144 °C
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.042 g/LALOGPS
logP3.53ALOGPS
logP3.14ChemAxon
logS-3.8ALOGPS
pKa (Strongest Basic)3.24ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area32.67 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity81.72 m³·mol⁻¹ChemAxon
Polarizability30.78 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-06z9-0190000000-e89bbe3f5be5dd2d8ef6Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-000i-0090000000-648ea07cfb54da221938Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-000i-0090000000-6fa6feb988c28cea9701Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-000i-0190000000-133e43f99f45b667ff8dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0fc0-1690000000-9b2cabcfe30f022505faSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-005a-2940000000-160b387e0e158e114ad3Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-003s-1920000000-afce32e992dcf0ffa799Spectrum
LC-MS/MSLC-MS/MS Spectrum - 15V, Positivesplash10-000i-0090000000-648ea07cfb54da221938Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-000i-0090000000-ed241329da9c26f2ad1eSpectrum
LC-MS/MSLC-MS/MS Spectrum - 60V, Positivesplash10-0fc0-1690000000-44693634010667152d40Spectrum
LC-MS/MSLC-MS/MS Spectrum - 45V, Positivesplash10-000i-0090000000-78f3056f8d14c06bdee3Spectrum
LC-MS/MSLC-MS/MS Spectrum - 90V, Positivesplash10-003s-1920000000-2eb3baa6cda1930497c8Spectrum
LC-MS/MSLC-MS/MS Spectrum - 75V, Positivesplash10-005a-2940000000-2402a3bd2d4706d4b407Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0090000000-481bd9921daf23c25723Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-1090000000-1da96f135036ef7911ebSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f6x-9330000000-4698b4ebfdf65cd11c90Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-13675d06f8c473dd2019Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0090000000-0b2235e8dd6ef6442946Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9430000000-ec79a12e3355732a7950Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-7183d771e959d0a76d02Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-1090000000-fba0c8f7d5e70241e1ffSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0019-5090000000-2a383ea900ba4439bcfbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0090000000-28b936e03152b6596fcdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0090000000-130637d1f671d168362fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01wo-1190000000-a458f36dd23549f29d15Spectrum
MSMass Spectrum (Electron Ionization)splash10-0udr-2690000000-03229b9979372af89a08Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityBenzodiazepines bind nonspecifically to benzodiazepine receptors BNZ1, which mediates sleep, and BNZ2, which affects affects muscle relaxation, anticonvulsant activity, motor coordination, and memory. As benzodiazepine receptors are thought to be coupled to gamma-aminobutyric acid-A (GABAA) receptors, this enhances the effects of GABA by increasing GABA affinity for the GABA receptor. Binding of the inhibitory neurotransmitter GABA to the site opens the chloride channel, resulting in a hyperpolarized cell membrane that prevents further excitation of the cell.
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesTetrazepam is used to treat muscle spasm, anxiety disorders such as panic attacks, or more rarely to treat depression, premenstrual syndrome or agoraphobia.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentGeneral supportive measures should be employed, along with intravenous fluids, and an adequate airway maintained. Hypotension may be combated by the use of norepinephrine or metaraminol. Dialysis is of limited value. Flumazenil (Anexate) is a competitive benzodiazepine receptor antagonist that can be used as an antidote for benzodiazepine overdose. In particular, flumazenil is very effective at reversing the CNS depression associated with benzodiazepines but is less effective at reversing respiratory depression. Its use, however, is controversial as it has numerous contraindications. It is contraindicated in patients who are on long-term benzodiazepines, those who have ingested a substance that lowers the seizure threshold, or in patients who have tachycardia or a history of seizures. As a general rule, medical observation and supportive care are the mainstay of treatment of benzodiazepine overdose. Although benzodiazepines are absorbed by activated charcoal, gastric decontamination with activated charcoal is not beneficial in pure benzodiazepine overdose as the risk of adverse effects often outweigh any potential benefit from the procedure. It is recommended only if benzodiazepines have been taken in combination with other drugs that may benefit from decontamination. Gastric lavage (stomach pumping) or whole bowel irrigation are also not recommended.
Concentrations
Not Available
DrugBank IDDB13324
HMDB IDHMDB0042029
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkTetrazepam
Chemspider ID23551
ChEBI IDNot Available
PubChem Compound ID25215
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available