General Description
White crystalline powder or granular solid with a slightly pungent odor. Bitter taste. Aqueous solutions neutral to litmus.
Reactivity Profile
PENTETRAZOL(54-95-5) 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.
Air & Water Reactions
Dust can be explosive when suspended in air at specific concentrations. Water soluble.
Fire Hazard
Flash point data for this chemical are not available. PENTETRAZOL is probably combustible.
Description
Pentylenetetrazole (PTZ) is a central nervous system modulator that is used to experimentally induce seizures in animals.
1 Subcutaneous PTZ has been used extensively to screen for compounds that block the production of nonconvulsive (absence or myoclonic) seizures.
2,3 PTZ has diverse, site-specific effects in the brain. However, it is an antagonist of GABA
A receptors and some drugs that block PTZ-induced seizures, including benzodiazepines, act at the GABA
A receptor.
4,5
Chemical Properties
white crystalline powder
Originator
Pentylenetetrazole,Spectrum Chemicals and
Uses
analeptic, circulation stimulant
Uses
Non-specific CNS stimulant; convulsant; narcotic antagonist.
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
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.
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.]
References
[1] L?SCHER W. Critical review of current animal models of seizures and epilepsy used in the discovery and development of new antiepileptic drugs[J]. Seizure-European Journal of Epilepsy, 2011, 20 5: Pages 359-368. DOI:
10.1016/j.seizure.2011.01.003[2] NATASHA T SNIDER. A cytochrome P450-derived epoxygenated metabolite of anandamide is a potent cannabinoid receptor 2-selective agonist.[J]. Molecular Pharmacology, 2009, 75 4: 965-972. DOI:
10.1124/mol.108.053439[3] KRISTIAN KAUFMANN. ML297 (VU0456810), the First Potent and Selective Activator of the GIRK Potassium Channel, Displays Antiepileptic Properties in Mice[J]. ACS Chemical Neuroscience, 2013, 4 9: 1278-1286. DOI:
10.1021/cn400062a[4] YOHAN CHAIX. Chemoconvulsant-induced Seizure Susceptibility: Toward a Common Genetic Basis?[J]. Epilepsia, 2007, 48 s5: 48-52. DOI:
10.1111/j.1528-1167.2007.01289.x[5] WHITE H S. Clinical Significance of Animal Seizure Models and Mechanism of Action Studies of Potential Antiepileptic Drugs[J]. Epilepsia, 2007, 38 s1: S9-S17. DOI:
10.1111/j.1528-1157.1997.tb04523.x
