P3053

Sigma-Aldrich

Penitrem A

≥95% (HPLC and TLC)

Synonym(s):
Tremortin A
Empirical Formula (Hill Notation):
C37H44ClNO6
CAS Number:
Molecular Weight:
634.20
MDL number:
PubChem Substance ID:
NACRES:
NA.77
Pricing and availability is not currently available.

Quality Level

assay

≥95% (HPLC and TLC)

storage temp.

2-8°C

SMILES string

[H][C@]12CC[C@@]3(C)[C@@](O)(CC[C@@]4([H])[C@]5([H])OC(C)(C)[C@@]6([H])C[C@]7([H])C(=C)Cc8c(Cl)cc9[nH]c(c5c9c8[C@]67O)[C@]34C)[C@]1%10O[C@]%10([H])[C@@H](O)[C@H](O2)C(C)=C

InChI

1S/C37H44ClNO6/c1-15(2)28-27(40)31-37(45-31)23(43-28)9-10-33(6)34(7)18(8-11-35(33,37)41)29-25-24-21(39-30(25)34)14-20(38)17-12-16(3)19-13-22(32(4,5)44-29)36(19,42)26(17)24/h14,18-19,22-23,27-29,31,39-42H,1,3,8-13H2,2,4-7H3/t18-,19+,22+,23-,27-,28+,29-,31+,33+,34+,35-,36+,37-/m0/s1

InChI key

JDUWHZOLEDOQSR-JKPSMKLGSA-N

Application

Penitrem A has been used as Ca2+-Activated K+ (BK) channel blocker to study its effect on BK current in bag cell neurons.

Packaging

1, 5 mg in glass bottle

Biochem/physiol Actions

Penitrem A intoxication causes ataxia, polypnea, and sustained tremors and may lead to seizures and death. Penitrem A affects the central and peripheral nervous system. It impairs the GABAergic neurotransmission in the cerebellum.

Features and Benefits

This compound is featured on the Potassium Channels page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Other Notes

Originally isolated from Penicillium palitans

Pictograms

Skull and crossbones

Signal Word

Danger

Hazard Statements

Precautionary Statements

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Hazard Codes

T+

Risk Statement

26/27/28

Safety Statement

36/37/39-45

RIDADR

UN 2811 6.1 / PGII

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis
Certificate of Origin
Silvio Uhlig et al.
Toxins, 12(5) (2020-05-08)
The tremorgenic mycotoxin penitrem A is produced by Penicillium species as a secondary metabolite on moldy food and feed. Dogs are sometimes exposed to penitrem A by consumption of spoiled food waste or fallen fruit. The lipophilic toxin crosses the...
W R Sones et al.
British journal of pharmacology, 158(2), 521-531 (2009-08-04)
Recent pharmacological studies have proposed there is a high degree of similarity between calcium-activated Cl(-) channels (CaCCs) and large conductance, calcium-gated K(+) channels (K(Ca)1.1). The goal of the present study was to ascertain whether blockers of K(Ca)1.1 inhibited calcium-activated Cl(-)...
H F Berntsen et al.
Neurotoxicology, 35, 129-136 (2013-01-15)
The fungal neurotoxin penitrem A has previously been found to cause neurological disorders in animals and humans after ingestion of contaminated food and/or feed. It penetrates the blood-brain-barrier and causes cerebellar pathology in rats, including mild effects on granule neurons....
Prolonged activation of ca2+-activated k+ current contributes to the long-lasting refractory period ofaplysia bag cell neurons
Zhang Y, et al.
The Journal of Neuroscience, 22(23), 10134-10141 (2002)
Roger D Kouyos et al.
PLoS pathogens, 7(4), e1001334-e1001334 (2011-05-03)
The evolution of drug resistant bacteria is a severe public health problem, both in hospitals and in the community. Currently, some countries aim at concentrating highly specialized services in large hospitals in order to improve patient outcomes. Emergent resistant strains...

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