Pentetrazol

Pentetrazol Basic information
Product Name:Pentetrazol
Synonyms:CARDIAZOLE;METRAZOLE;1,5-PENTAMETHYLENETETRAZOLE;1,5-PENTAMETHYLENE-1H-TETRAZOLE;6,7,8,9-TETRAHYDRO-5H-TETRAZOLO-[1,5-A]AZEPINE;6,7,8,9-TETRAHYDRO-5H-TETRAZOLOAZEPINE;ALPHA,BETA-CYCLOPENTAMETHYLENETETRAZOLE;PENTAMETHYLENETETRAZOLE
CAS:54-95-5
MF:C6H10N4
MW:138.17
EINECS:200-219-3
Product Categories:CARDIAZOL;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
Mol File:54-95-5.mol
Pentetrazol Structure
Pentetrazol Chemical Properties
Melting point 59-61 °C (lit.)
Boiling point 194 °C/12 mmHg (lit.)
density 1.0617 (rough estimate)
refractive index 1.4910 (estimate)
Fp 194°C/12mm
storage temp. -20°C
solubility ≥15.38 mg/mL in EtOH; ≥6.3 mg/mL in DMSO; ≥83.2 mg/mL in H2O
pka1.25±0.20(Predicted)
form solid
color White, crystalline powder
Sensitive Hygroscopic
Merck 14,7141
BRN 135492
Stability:Stable. Incompatible with strong oxidizing agents.
InChIKeyCWRVKFFCRWGWCS-UHFFFAOYSA-N
CAS DataBase Reference54-95-5(CAS DataBase Reference)
NIST Chemistry ReferencePentylenetetrazol(54-95-5)
EPA Substance Registry SystemPentetrazol (54-95-5)
Safety Information
Hazard Codes T
Risk Statements 25-36/37/38-23/24/25
Safety Statements 26-36/37/39-45
RIDADR UN 2811 6.1/PG 3
WGK Germany 3
RTECS XF8225000
TSCA Yes
HazardClass 6.1
PackingGroup II
ToxicityLD50 in rats (mg/kg): 85±2 s.c., 62 i.p. (Goldenthal)
MSDS Information
ProviderLanguage
1,5-Pentamethylene-1H-tetrazole English
SigmaAldrich English
ALFA English
Pentetrazol Usage And Synthesis
DescriptionPentylenetetrazole (PTZ) is a central nervous system modulator that is used to experimentally induce seizures in animals. Subcutaneous PTZ has been used extensively to screen for compounds that block the production of nonconvulsive (absence or myoclonic) seizures. PTZ has diverse, site-specific effects in the brain. However, it is an antagonist of GABAA receptors and some drugs that block PTZ-induced seizures, including benzodiazepines, act at the GABAA receptor.
Chemical Propertieswhite crystalline powder
OriginatorPentylenetetrazole,Spectrum Chemicals and
UsesPentylenetetrazole has been used to induce seizures in zebra fish larvae, mice, and male wistar rats.
UsesNon-specific CNS stimulant; convulsant; narcotic antagonist.
Usesanaleptic, circulation stimulant
DefinitionChEBI: An organic heterobicyclic compound that is 1H-tetrazole in which the hydrogens at positions 1 and 5 are replaced by a pentane-1,5-diyl group. A central and respiratory stimulant, it was formerly used for the treatment of cough and other espiratory tract disorders, cardiovascular disorders including hypotension, and pruritis.
Manufacturing ProcessA solution of 9.8 g cyclohexanone and 8.6 g HNO3 in about 250 ml benzene were slowly added dropwise to 20 ml concentrate sulfuric acid in 100 ml benzene by ice cooling and stirring. After ending of a generation of N2 (0.1 moles) to a corresponding quantity of cyclohexane (0.1 moles). Acid layer was diluted with ice, and made neutral with strong alkaline to give a reaction product as oil. Then it was exrtacted with chloroform, all solvents were distilled and the residue was diluted with water. The desired 6,7,8,9tetrahydro-5H-tetrazoloazepine dropped. Yield was 7.5 g after recrystallization from ester or distillation. M.P: 65°C.
Brand nameCardiazol (Knoll).
Therapeutic FunctionAnaleptic, Central stimulant
General DescriptionWhite crystalline powder or granular solid with a slightly pungent odor. Bitter taste. Aqueous solutions neutral to litmus.
Air & Water ReactionsDust can be explosive when suspended in air at specific concentrations. Water soluble.
Reactivity ProfilePentetrazol is incompatible with oxidizing agents. . Azo, diazo, azido compounds can detonate. This applies in particular to organic azides that have been sensitized by the addition of metal salts or strong acids. Toxic gases are formed by mixing materials of this class with acids, aldehydes, amides, carbamates, cyanides, inorganic fluorides, halogenated organics, isocyanates, ketones, metals, nitrides, peroxides, phenols, epoxides, acyl halides, and strong oxidizing or reducing agents. Flammable gases are formed by mixing materials in this group with alkali metals. Explosive combination can occur with strong oxidizing agents, metal salts, peroxides, and sulfides. Azo dyes can be explosive when suspended in air at specific concentrations.
Fire HazardFlash point data for Pentetrazol are not available. Pentetrazol is probably combustible.
Biological ActivityCNS stimulant that induces kindling in vivo . Causes alterations in excitatory and inhibitory neurotransmitter systems.
Biochem/physiol ActionsPentylenetetrazole is a non-specific central nervous system (CNS) stimulant and convulsant. PTZ induces oxidative stress and increases cortical malondialdehyde content and affects hippocampus, resulting in seizures.
Safety ProfileA human poison by ingestion and intravenous routes. Poison experimentally by ingestion, intravenous, intraperitoneal, subcutaneous, rectal, and parenteral routes. When heated to decomposition it emits toxic fumes of NOx.
storage-20°C
Purification MethodspKEst Crystallise metrazol from diethyl ether and dry it under vacuum over P2O5, or distil it. [Schmidt Chem Ber 57 704 1924, Beilstein 26 II 213.]
Pentetrazol Preparation Products And Raw materials
Raw materialsSulfuric acid-->Cyclohexanone-->Nitric acid
Ribavirin 5-Methyl-1H-benzotriazole Penconazole Tolyltriazole 1,2,3-1H-Triazole 1-CHLOROMETHYL-1H-1,2,4-TRIAZOLE Methylene Blue trihydrate Tetrazole Pentetrazol 1H-Benzotriazole 1H-Tetrazole-1-acetic acid 1-TETRACENE Oxymetholone Pentaerythritol Dimethyl sulfoxide Tebuconazole Nitrotetrazolium blue chloride 2,3,5-Triphenyltetrazolium chloride

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