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P6500

Sigma-Aldrich

Pentylenetetrazole

≥99% (GC), powder, CNS stimulant

Synonym(s):

α,β-Cyclopentamethylenetetrazole, 1,5-Pentamethylenetetrazole, 6,7,8,9-Tetrahydro-5H-tetrazolo[1,5-a]azepine, Metrazole

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About This Item

Empirical Formula (Hill Notation):
C6H10N4
CAS Number:
54-95-5
Molecular Weight:
138.17
EC Number:
200-219-3
MDL number:
MFCD00005939
UNSPSC Code:
12352200
PubChem Substance ID:
24278643
NACRES:
NA.77

product name

Pentylenetetrazole,

form

powder

bp

194 °C/12 mmHg (lit.)

mp

59-61 °C (lit.)

storage temp.

−20°C

SMILES string

C1CCc2nnnn2CC1

InChI

1S/C6H10N4/c1-2-4-6-7-8-9-10(6)5-3-1/h1-5H2

InChI key

CWRVKFFCRWGWCS-UHFFFAOYSA-N

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General description

Pentylenetetrazole (PTZ) is a tetrazole derivative and inhibitor of the γ aminobutyric acid (GABAA) and its receptor complex. PTZ is a convulsing agent used for inducing seizures. It can traverse the blood-brain barrier.

Application

Pentylenetetrazole has been used to induce seizures in zebra fish larvae, mice, and male wistar rats.

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.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H301,H315,H319,H335

Hazard Classifications

Acute Tox. 3 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Mehwish Anwer et al.
Scientific reports, 9(1), 11819-11819 (2019-08-16)
Traumatic brain injury (TBI) causes neuroendocrine dysregulation in up to 40% of humans, which is related to impaired function of the hypothalamo-hypophyseal axis and contributes to TBI-related co-morbidities. Our objective was to investigate whether hypophyseal atrophy can be recapitulated in
Perineuronal net degradation in epilepsy
Rankin-Gee EK, et al.
Epilepsia, 56(7), 1124-1133 (2015)
Optical mapping of neuronal activity during seizures in zebrafish
Turrini L, et al.
Scientific reports, 7(1), 3025-3025 (2017)
Tatiana Afrikanova et al.
PloS one, 8(1), e54166-e54166 (2013-01-24)
Zebrafish have recently emerged as an attractive in vivo model for epilepsy. Seven-day-old zebrafish larvae exposed to the GABA(A) antagonist pentylenetetrazol (PTZ) exhibit increased locomotor activity, seizure-like behavior, and epileptiform electrographic activity. A previous study showed that 12 out of
Ervand G Paronikyan et al.
MedChemComm, 10(8), 1399-1411 (2019-09-20)
8-Hydrazino derivatives of pyrano[3,4-c]pyridines and derivatives of the new heterocyclic system 3-thioxopyrano[3,4-c][1,2,4]triazolo[4,3-a]pyridines on the basis of methanesulfonates of pyrano[3,4-c]pyridinium were synthesized by optimization of a previously used method. Derivatives of alkylsulfonyl pyrano[3,4-c][1,2,4]triazolo[4,3-a]pyridines were also synthesized. All compounds were evaluated for
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