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P3053

Sigma-Aldrich

Penitrem A

≥95% (HPLC and TLC)

Synonym(s):

Tremortin A

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About This Item

Empirical Formula (Hill Notation):
C37H44ClNO6
CAS Number:
12627-35-9
Molecular Weight:
634.20
MDL number:
MFCD00083465
UNSPSC Code:
12352200
PubChem Substance ID:
24898385
NACRES:
NA.77

Quality Level

200

Assay

≥95% (HPLC and TLC)

form

powder

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.

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
GHS06

Signal Word

Danger

Hazard Statements

H300

Precautionary Statements

P301 + P330 + P331 + P310

Hazard Classifications

Acute Tox. 2 Oral

Storage Class Code

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

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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Peter R Lewis et al.
The Medical journal of Australia, 182(11), 582-584 (2005-06-09)
We report on an elderly couple who presented with a syndrome that included severe generalised tremor and incoordination after eating soup from a damaged can. Black mould contaminating the can was subcultured and the fungus Penicillium crustosum was identified. This
Claudia Welz et al.
PLoS pathogens, 7(4), e1001330-e1001330 (2011-04-15)
The calcium-gated potassium channel SLO-1 in Caenorhabditis elegans was recently identified as key component for action of emodepside, a new anthelmintic drug with broad spectrum activity. In this study we identified orthologues of slo-1 in Ancylostoma caninum, Cooperia oncophora, and
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.
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(-)
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