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P3053

Sigma-Aldrich

Penitrem A

≥95% (HPLC and TLC)

Synonym(s):

Tremortin A

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₩427,620
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₩1,595,073

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1 MG
₩427,620
5 MG
₩1,595,073

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

₩427,620

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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.[1]

Biochem/physiol Actions

Penitrem A intoxication causes ataxia, polypnea, and sustained tremors and may lead to seizures and death.[2] Penitrem A affects the central and peripheral nervous system. It impairs the GABAergic neurotransmission in the cerebellum.[3]

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

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Certificates of Analysis (COA)

Lot/Batch Number
0000317540
0000317541
0000317541
0000317540
0000088368

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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)
Karen D McCloskey
The Journal of urology, 173(1), 296-301 (2004-12-14)
Outward currents were characterized from cells resembling interstitial cells of Cajal (ICCs) isolated from the detrusor of the guinea pig bladder. ICC-like cells were studied using the whole cell patch clamp technique and K+ filled pipettes. Outward currents were evoked
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