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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
Molecular Weight:
634.2
MDL Number:
MFCD12547934
MOL File:
12627-35-9.mol
MSDS File:
SDS
Last updated:2023-06-30 15:45:59

PENITREM A Properties

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.
EWG's Food Scores 1
FDA UNII 244AU85PR7

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS06
Signal word  Danger
Hazard statements  H300
Precautionary statements  P301+P330+P331+P310
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
NFPA 704
0
4 0

PENITREM A price More Price(16)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich P3053 Penitrem A ≥95% (HPLC and TLC) 12627-35-9 1mg $340 2024-03-01 Buy
Sigma-Aldrich P3053 Penitrem A ≥95% (HPLC and TLC) 12627-35-9 5mg $1220 2024-03-01 Buy
Cayman Chemical 11347 Penitrem A ≥98% 12627-35-9 1mg $41 2024-03-01 Buy
Cayman Chemical 11347 Penitrem A ≥98% 12627-35-9 5mg $152 2024-03-01 Buy
Cayman Chemical 11347 Penitrem A ≥98% 12627-35-9 10mg $284 2024-03-01 Buy
Product number Packaging Price Buy
P3053 1mg $340 Buy
P3053 5mg $1220 Buy
11347 1mg $41 Buy
11347 5mg $152 Buy
11347 10mg $284 Buy

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

Uses

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

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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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