4-Acetyl-1,1-dimethylpiperazinium iodide - CAS 75667-84-4
Category: Inhibitor
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Molecular Formula:
C8H17IN2O
Molecular Weight:
284.14
COA:
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Targets:
nAChR
Description:
4-Acetyl-1,1-dimethylpiperazinium iodide is a structural analog of acetylcholine, which is a nicotinic (AChR) agonist with Ki value of 29.9 nM at α4β2.
Synonyms:
1,1-Dimethyl-4-acetylpiperazinium Iodide; IEM 909
MSDS:
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InChIKey:
VXBLRKDEHGKPAC-UHFFFAOYSA-M
InChI:
InChI=1S/C8H17N2O.HI/c1-8(11)9-4-6-10(2,3)7-5-9;/h4-7H2,1-3H3;1H/q+1;/p-1
Canonical SMILES:
CC(=O)N1CC[N+](CC1)(C)C.[I-]
1.Identification of a new amino acid residue capable of modulating agonist efficacy at the homomeric nicotinic acetylcholine receptor, alpha7.
Vazquez RW;Oswald RE Mol Pharmacol. 1999 Jan;55(1):1-7.
Neuronal nicotinic receptors (nAChRs) have been implicated in pathology associated with neurological diseases and aberrant cognitive states such as addiction and schizophrenia. The design of subtype-specific cholinergic drugs is dependent on identification of key amino acids that play a significant role in determining subunit-specific agonist efficacy. 1,1-Dimethyl-4-phenylpiperazinium (DMPP) and a series of piperazium (PIP)-derived cholinergic agonists (1,1 dimethyl-4-acetylpiperizinium iodide, EthylPIP, PropylPIP, and ButylPIP) were used to identify a site (position 84) in homomeric neuronal nAChRs, which is a partial determinant of pharmacological specificity. In contrast to absolutely conserved amino acids within the nicotinic superfamily, the amino acid in position 84 can be polar or nonpolar. The addition of one methylene to PropylPIP to form ButylPIP eliminated channel activation of but not binding to the chick alpha7 homomeric nAChR (leucine in position 84). In rat alpha7 (glutamine in position 84), ButylPIP was an agonist. 1, 1-Dimethyl-4-phenylpiperazinium, a structural analog of ButylPIP, activates the rat alpha7 but is a weak partial agonist of the chick alpha7. Mutation of the chick alpha7 (L84Q) restored activation by ButylPIP, and the corresponding mutation in rat alpha7 (Q84L) abolished activation by ButylPIP.
2.Structural and electronic requirements for potent agonists at a nicotinic receptor.
Spivak CE;Gund TM;Liang RF;Waters JA Eur J Pharmacol. 1986 Jan 14;120(1):127-31.
A new agonist, isoarecolone methiodide (1,1-dimethyl-4-acetyl-1,2,3,6-tetrahydropyridinium iodide) was tested at the frog neuromuscular junction. It was 50 times more potent than carbamylcholine, making it one of the most potent nicotinic agonists known. In addition, its cyclic structure and conjugated carbonyl bond endow it with near rigidity. An analogous compound, 1,1-dimethyl-4-acetylpiperazinium iodide, was synthesized because of its similar geometry and rigidity. It was 2.6 times as potent as carbamylcholine but only 0.053 times as potent as isoarecolone methiodide. Computer assisted molecular modeling and molecular orbital calculations revealed steric and electrostatic field differences between these two compounds.
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Chemical Structure

CAS 75667-84-4 4-Acetyl-1,1-dimethylpiperazinium iodide

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