paraherquamide

paraherquamide Structure
CAS No.
77392-58-6
Chemical Name:
paraherquamide
Synonyms
VM 29919;paraherquamide;(-)-Paraherquamide A;Spiro[4H,8H-[1,4]dioxepino[2,3-g]indole-8,7'(8'H)-[5H,6H-5a,9a](iminomethano)[1H]cyclopent[f]indolizine]-9,10'(10H)-dione, 2',3',8'a,9'-tetrahydro-1'-hydroxy-1',4,4,8',8',11'-hexamethyl-, (1'R,5'aS,7'R,8'aS,9'aR)-
CBNumber:
CB51336725
Molecular Formula:
C28H35N3O5
Molecular Weight:
493.59
MOL File:
77392-58-6.mol
Modify Date:
2023/6/8 9:03:09

paraherquamide Properties

Melting point 244-247° (dec)
alpha D22 -28° (c = 0.43 in methanol)
storage temp. Store at -20°C
solubility DMF: soluble; DMSO: soluble; Ethanol: soluble; Methanol: soluble
form White to off-white powder.

SAFETY

Risk and Safety Statements

Symbol(GHS) 
GHS06
Signal word  Danger
Hazard statements  H300
Precautionary statements  P264-P270-P301+P310-P321-P330-P405-P501
NFPA 704
0
4 0

paraherquamide Chemical Properties,Uses,Production

Description

Paraherquamide A is a mycotoxin anthelmintic originally isolated from P. paraherquei. It binds to acetylcholine receptors (IC50 = 0.5 nM for head homogenates of M. domestica) and acts as an antagonist. Paraherquamide A is toxic to C. elegans (LD50 = 2.5 μg/ml) and effective against T. colubriformis infection in gerbils when used at doses ranging from 0.39 to 200 mg/kg. It is toxic to mice (LD50 = 14.9 mg/kg).

Uses

Paraherquamide A was first reported as a mycotoxin related to the indole tremorgenic mycotoxins. Subsequent research identified a potent, non-toxic paralysis of nematodes which led to the metabolite's development as a candidate anthelmintic. Paraherquamide A is a selective, competitive, cholinergic antagonist that distinguishes subtypes of cholinergic receptors.

paraherquamide Preparation Products And Raw materials

Raw materials

Preparation Products

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paraherquamide VM 29919 Spiro[4H,8H-[1,4]dioxepino[2,3-g]indole-8,7'(8'H)-[5H,6H-5a,9a](iminomethano)[1H]cyclopent[f]indolizine]-9,10'(10H)-dione, 2',3',8'a,9'-tetrahydro-1'-hydroxy-1',4,4,8',8',11'-hexamethyl-, (1'R,5'aS,7'R,8'aS,9'aR)- (-)-Paraherquamide A 77392-58-6