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Merck

P6500

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
NACRES:
NA.77
PubChem Substance ID:
24278643
UNSPSC Code:
12352200
EC Number:
200-219-3
MDL number:
MFCD00005939
Form:
powder
Quality level:
100

Key Documents

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Product Name

Pentylenetetrazole,

InChI key

CWRVKFFCRWGWCS-UHFFFAOYSA-N

InChI

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

SMILES string

C1CCc2nnnn2CC1

form

powder

bp

194 °C/12 mmHg (lit.)

mp

59-61 °C (lit.)

storage temp.

−20°C

Quality Level

100

Related Categories

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

signalword

Danger

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

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

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

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Certificates of Analysis (COA)

Lot/Batch Number
MKCX5352
MKCW6132
MKCT1250
MKCS5163
MKCR2882

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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
Optical mapping of neuronal activity during seizures in zebrafish
Turrini L, et al.
Scientific reports, 7(1), 3025-3025 (2017)
Posterior hypothalamus glutamate infusion decreases pentylenetetrazol-induced seizures of male rats through hippocampal histamine increase
Arzhang A, et al.
Pharmacology, Biochemistry, and Behavior, 158, 7-13 (2017)
Perineuronal net degradation in epilepsy
Rankin-Gee EK, et al.
Epilepsia, 56(7), 1124-1133 (2015)
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
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