ChemicalBook > CAS DataBase List > PENITREM A

PENITREM A

Product Name
PENITREM A
CAS No.
12627-35-9
Chemical Name
PENITREM A
Synonyms
PENITREM A;TREMORTIN A;JDUWHZOLEDOQSR-JKPSMKLGSA-N;Penitrem A Nsc354845;PENITREM A, PENICILLIUM PAXILLI;Penitrem A from Penicillium paxilli;penitrem A from penicillium palitans;7,8-(Epoxymethano)-2H,6H-cyclobuta[5,6]benz[1,2-e]oxireno[4',4'a]-1-benzopyrano[5',6':6,7]indeno[1,2-b]indole-3,4b,7d(5H,7H)-triol, 12-chloro-3,3a,6a,8,9,9a,10,11,14,14b,14c,15,16,16a-tetradecahydro-14b,14c,17,17-tetramethyl-10-methylene-2-(1-methylethenyl)-, (2R,3S,3aR,4aS,4bS,6aR,7S,7dR,8R,9aR,14b...;2R,3S,3aR,4aS,4bS,6aR,7S,7dR,8R,9aR,14bS,14cR,16aS)-12-chloro-3,3a,6a,8,9,9a,10,11,14,14b,14c,15,16,16a-tetradecahydro-14b,14c,17,17-tetramethyl-10-methylene-2-(1-methylethenyl)-7,8-(epoxymethano)-2H,6H-cyclobuta[5,6]benz[1,2-e]oxireno[4',4'a]-1-benzopyrano[5',6':6,7]indeno[1,2-b]indole-3,4b,7d(5H,7H)-triol
CBNumber
CB4155421
Molecular Formula
C37H44ClNO6
Formula Weight
634.2
MOL File
12627-35-9.mol
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PENITREM A Property

Melting point:
238°C
Density 
1.0241 (rough estimate)
refractive index 
1.6000 (estimate)
storage temp. 
2-8°C
solubility 
Soluble in DMSO (up to 6 mg/ml)
form 
White solid.
pka
13.22±0.70(Predicted)
color 
Amorphous solid
Stability:
Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 3 months.
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Safety

Hazard Codes 
T+,T
Risk Statements 
26/27/28
Safety Statements 
36/37/39-45
RIDADR 
UN 2811 6.1/PG 2
WGK Germany 
3
RTECS 
RY7535000
HazardClass 
6.1(a)
PackingGroup 
II
HS Code 
29349990
Toxicity
LD50 orl-mus: 10 mg/kg 41KEAL -,108,78
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H300Fatal if swallowed

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
P3053
Product name
Penitrem A
Purity
≥95% (HPLC and TLC)
Packaging
1mg
Price
$340
Updated
2024/03/01
Sigma-Aldrich
Product number
P3053
Product name
Penitrem A
Purity
≥95% (HPLC and TLC)
Packaging
5mg
Price
$1220
Updated
2024/03/01
Cayman Chemical
Product number
11347
Product name
Penitrem A
Purity
≥98%
Packaging
1mg
Price
$41
Updated
2024/03/01
Cayman Chemical
Product number
11347
Product name
Penitrem A
Purity
≥98%
Packaging
5mg
Price
$152
Updated
2024/03/01
Cayman Chemical
Product number
11347
Product name
Penitrem A
Purity
≥98%
Packaging
10mg
Price
$284
Updated
2024/03/01
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PENITREM A Chemical Properties,Usage,Production

Description

Penitrem A (12627-35-9) is a fungal mycotoxin that acts as a selective, irreversible blocker of the smooth muscle high conductance Ca2+-activated K+?(BK, KCa1.1) channel (100% block at 10 nM).1?Displays brain neurotoxicity in rats along with dose-dependent convulsions and death.2?An important tool for studying the role of BK channels in vascular function which is effective in cellular, tissue and?in vivo?experiments.3?Inhibits BK channels in inside-out and cell-attached patches, whereas iberiotoxin (considered the gold standard BK channel blocker) does not.3?May be used to partially ablate Purkinje cells in immature rat cerebellum providing a model for neural stem cell transplantation studies.4

Chemical Properties

Solid

Occurrence

A series of closely related metabolites of Penicillium crustosum has recently been isolated and the components separated chromatographically. Penitrem A forms colourless crystals from EtOH.

Uses

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

Uses

Penitrem A is a tremorgenic mycotoxin isolated from Penicillium species. Penitrem A is a selective blocker of high-conductance Ca2+-activated potassium channels.

Definition

ChEBI: Penitrem A is an organooxygen compound and an organic heterotricyclic compound.

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.

Safety Profile

Poison by ingestion and intraperitoneal routes. An experimental teratogen. When heated to decomposition it emits very toxic fumes of Clí and NOx.

storage

-20°C

References

References/Citations:

PENITREM A Preparation Products And Raw materials

Raw materials

Preparation Products

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12627-35-9, PENITREM ARelated Search:

Penicillin G potassium salt D-Penicillamine CYCLOPENT[B]INDOLE, 1,2,3,4-TETRAHYDRO-7-METHYL- 4-TERT-AMYLCYCLOHEXANOL TRANS-4-TERT-BUTYLCYCLOHEXANOL Dihydromyrcenol 4-tert-Butylcyclohexanol 5-Ethylindole (R)-(-)-Methyl glycidyl ether 4-Methylindole Ethylhexylglycerin TRANS-4-TERT-PENTYLCYCLOHEXANOL 2,5-Dimethylindole (+/-)-GEOSMIN (1R)-1-(3-CHLOROPHENYL)ETHANOL 1-Phenylcyclobutane-1-ol 1-CYCLOBUTYLETHANOL 2,4-DIMETHYL-1H-INDOLE

  • TREMORTIN A
  • Penitrem A from Penicillium paxilli
  • PENITREM A
  • PENITREM A, PENICILLIUM PAXILLI
  • penitrem A from penicillium palitans
  • Penitrem A Nsc354845
  • JDUWHZOLEDOQSR-JKPSMKLGSA-N
  • 2R,3S,3aR,4aS,4bS,6aR,7S,7dR,8R,9aR,14bS,14cR,16aS)-12-chloro-3,3a,6a,8,9,9a,10,11,14,14b,14c,15,16,16a-tetradecahydro-14b,14c,17,17-tetramethyl-10-methylene-2-(1-methylethenyl)-7,8-(epoxymethano)-2H,6H-cyclobuta[5,6]benz[1,2-e]oxireno[4',4'a]-1-benzopyrano[5',6':6,7]indeno[1,2-b]indole-3,4b,7d(5H,7H)-triol
  • 7,8-(Epoxymethano)-2H,6H-cyclobuta[5,6]benz[1,2-e]oxireno[4',4'a]-1-benzopyrano[5',6':6,7]indeno[1,2-b]indole-3,4b,7d(5H,7H)-triol, 12-chloro-3,3a,6a,8,9,9a,10,11,14,14b,14c,15,16,16a-tetradecahydro-14b,14c,17,17-tetramethyl-10-methylene-2-(1-methylethenyl)-, (2R,3S,3aR,4aS,4bS,6aR,7S,7dR,8R,9aR,14b...
  • 12627-35-9
  • C37H44ClNO6
  • BioChemical
  • Cell Signaling and Neuroscience
  • Cell Biology
  • Monovalent Ion Channels
  • Potassium Channel Modulators
  • Ion Channels
  • Voltage-gated Ion Channels
  • antibiotic