Pentetrazol

Base Information

• Chemical Name: Pentetrazol
• CAS No.: 54-95-5
• Molecular Formula: C6H10 N4
• Molecular Weight: 138.172
• Hs Code.: 2933990090
• European Community (EC) Number: 200-219-3
• NSC Number: 759592,66489,5729
• UN Number: 2811
• UNII: WM5Z385K7T
• DSSTox Substance ID: DTXSID7041091
• Nikkaji Number: J22.644K
• Wikipedia: Pentylenetetrazol
• Wikidata: Q412391
• NCI Thesaurus Code: C81054
• Metabolomics Workbench ID: 67510
• ChEMBL ID: CHEMBL116943
• Mol file: 54-95-5.mol

Synonyms:Cardiazol;Corasol;Corazol;Corazole;Korazol;Korazole;Leptazole;Metrazol;Metrazole;Pentamethylenetetrazole;Pentazol;Pentetrazole;Pentylenetetrazol;Pentylenetetrazole

Chemical Property of Pentetrazol

Chemical Property:

• Appearance/Colour: white crystalline powder
• Vapor Pressure: 9.27E-05mmHg at 25°C
• Melting Point: 59-61 ºC
• Refractive Index: 1.4910 (estimate)
• Boiling Point: 194 ºC (12 mmHg)
• PKA: 1.25±0.20(Predicted)
• Flash Point: 194°C/12mm
• PSA: 43.60000
• Density: 1.42g/cm³
• LogP: 0.39950
• Storage Temp.: −20°C
• Sensitive.: Hygroscopic
• Solubility.: ≥15.38 mg/mL in EtOH; ≥6.3 mg/mL in DMSO; ≥83.2 mg/mL in H2O
• Water Solubility.: >=10 g/100 mL at 21 C
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 138.090546336
• Heavy Atom Count: 10
• Complexity: 116
• Transport DOT Label: Poison

Purity/Quality:

99%, ^*data from raw suppliers

Pentylenetetrazole ^*data from reagent suppliers

Safty Information:

• Hazard Codes: T
• Statements: 25-36/37/38-23/24/25
• Safety Statements: 26-36/37/39-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1CCC2=NN=NN2CC1
• Recent ClinicalTrials: PMT for MDRO Decolonization
• Recent EU Clinical Trials: A PHASE 2 MONOCENTRIC PILOT STUDY TO EVALUATE THE EFFICACY AND SAFETY PROFILE OF PIOGLITAZONE IN SUBJECTS WITH ACTIVE NON-SEGMENTAL VITILIGO
• 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.
• Uses: Pentylenetetrazole has been used to induce seizures in zebra fish larvae, mice, and male wistar rats. Non-specific CNS stimulant; convulsant; narcotic antagonist. analeptic, circulation stimulant
• Therapeutic Function: Analeptic, Central stimulant

Technology Process of Pentetrazol

There total 16 articles about Pentetrazol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

cyclohexanone (108-94-1,11119-77-0,9003-41-2,9075-99-4) → pentetrazole (54-95-5)

Guidance literature:

With sodium azide; tetrachlorosilane; In acetonitrile; for 20h; Ambient temperature;

DOI:10.1016/0040-4039(95)01513-H

Reference yield: 94.0%

cyclohexanone oxime methanesulfonate (80053-69-6) → pentetrazole (54-95-5)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In acetonitrile; for 24h; Heating;

DOI:10.1246/bcsj.58.2419

Reference yield: 91.0%

cyclohexanone (108-94-1,11119-77-0,9003-41-2,9075-99-4) → pentetrazole (54-95-5) + 4,5,6,7,8,9-hexahydrotetrazolo[1,5-a][1,3]diazocine

Guidance literature:

With trifluorormethanesulfonic acid; trimethylsilylazide; at 20 ℃; for 2h; Inert atmosphere; Sealed tube;

DOI:10.1021/acs.joc.5b02764

upstream raw materials:

caprolactam

1-azacycloheptane-2-thione

O-methylcaprolactim

7-ethylsulfanyl-3,4,5,6-tetrahydro-2H-azepine

Downstream raw materials:

phenyl(6,7,8,9-tetrahydro-5H-tetrazolo[1,5-a]azepin-9-yl)methyl acetate

9-benzylidene-6,7,8,9-tetrahydro-5H-tetrazolo[1,5-a]azepine

Refernces

• 1、 Ishihara, Kotaro,Shioiri, Takayuki,Matsugi, Masato. "Stereospecific synthesis of 1,5-disubstituted tetrazoles from ketoximes via a Beckmann rearrangement facilitated by diphenyl phosphorazidate". supporting information. p. 1295 - 1298. Retrieved 2019/04/13.
• 2、 Motiwala, Hashim F.,Charaschanya, Manwika,Day, Victor W.,Aubé, Jeffrey. "Remodeling and Enhancing Schmidt Reaction Pathways in Hexafluoroisopropanol". . p. 1593 - 1609. Retrieved 2016/03/01.