54-95-5 Usage
Description
Pentylenetetrazole (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 Properties
white crystalline powder
Originator
Pentylenetetrazole,Spectrum Chemicals and
Uses
Different sources of media describe the Uses of 54-95-5 differently. You can refer to the following data:
1. Pentylenetetrazole has been used to induce seizures in zebra fish larvae, mice, and male wistar rats.
2. Non-specific CNS stimulant; convulsant; narcotic antagonist.
3. analeptic, circulation stimulant
Definition
ChEBI: 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 Process
A 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 name
Cardiazol (Knoll).
Therapeutic Function
Analeptic, Central stimulant
General Description
White crystalline powder or granular solid with a slightly pungent odor. Bitter taste. Aqueous solutions neutral to litmus.
Air & Water Reactions
Dust can be explosive when suspended in air at specific concentrations. Water soluble.
Reactivity Profile
Pentetrazol 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 Hazard
Flash point data for Pentetrazol are not available. Pentetrazol is probably combustible.
Biological Activity
CNS stimulant that induces kindling in vivo . Causes alterations in excitatory and inhibitory neurotransmitter systems.
Biochem/physiol Actions
Pentylenetetrazole 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 Profile
A 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.
Purification Methods
pKEst 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.]
Check Digit Verification of cas no
The CAS Registry Mumber 54-95-5 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 5 and 4 respectively; the second part has 2 digits, 9 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 54-95:
(4*5)+(3*4)+(2*9)+(1*5)=55
55 % 10 = 5
So 54-95-5 is a valid CAS Registry Number.
InChI:InChI=1/C6H10N4/c1-2-4-6-7-8-9-10(6)5-3-1/h1-5H2
54-95-5Relevant articles and documents
Preparation of 1,5-fused tetrazoles under solvent-free conditions
Eshghi, Hossein,Hassankhani, Asadollah
, p. 1115 - 1120 (2005)
A facile and efficient procedure is developed for a one-pot synthesis of fused 1,5-disubstituted tetrazoles from cyclic ketones and sodium azide in the presence of aluminum chloride in solvent-free media. Advantages of this method are chemoselectivity, with high yields in a simple operation, and short reaction time under solvent-free conditions. Copyright Taylor & Francis, Inc.
An Interrupted Schmidt Reaction: C-C Bond Formation Arising from Nitrilium Ion Capture
Charaschanya, Manwika,Li, Kelin,Motiwala, Hashim F.,Aubé, Jeffrey
supporting information, p. 6354 - 6358 (2018/10/15)
The rerouting of the nitrilium ion formed in the Schmidt reaction of ketones and TMSN3 to encompass C-C bond formation with an electron-rich aromatic group is reported. Thus, when the reaction is carried out in HFIP using AlCl3 or Al
Convergent Three-Component Tetrazole Synthesis
Chandgude, Ajay L.,D?mling, Alexander
, p. 2383 - 2387 (2016/06/01)
A microwave-accelerated, simple, and efficient method for the construction of the 1,5-tetrazole scaffold was developed. It comprises a multicomponent reaction of an amine, a carboxylic acid derivative, and an azide source. On the basis of the availability of the archetypical starting materials, this method provided very versatile synthetic access to 1,5-disubstituted tetrazoles. The usefulness of this method was demonstrated in the synthesis of biologically important fused tetrazole scaffolds and the marketed drug cilostazol.
