84226-06-2

Usage

Uses

Used in Neurology:
BENZAMIDE, N-[(1-ETHYL-2-PYRROLIDINYL)METHYL]-2-HYDROXY-3-IODO-6-METHOXYis used as a radioligand for non-invasive quantification of D2-like dopamine receptors in brain studies for the differentiation of Parkinson's disease from other neurodegenerative diseases like Lewy Body dementia and multiple system atrophy.

InChI:InChI=1/C15H21IN2O3/c1-3-18-8-4-5-10(18)9-17-15(20)13-12(21-2)7-6-11(16)14(13)19/h6-7,10,19H,3-5,8-9H2,1-2H3,(H,17,20)/t10-/m0/s1

Upstream product

• 3147-64-6 2-hydroxy-6-methoxybenzoic acid 
• 22795-99-9 (S)-2-(Aminomethyl)-1-ethylpyrrolidine 
• 84226-04-0 (-)-BZM 
• 90347-70-9 3-iodo-2,6-dimethoxybenzoic acid 
• 113452-76-9 3-iodo-6-methoxysalicylic acid 
• 96897-88-0 N-((S)-1-Ethyl-pyrrolidin-2-ylmethyl)-3-iodo-2,6-dimethoxy-benzamide 
• 1466-76-8 2-6-dimethoxybenzoic acid 

Downstream Products

• 1574609-55-4 N-[(1-ethyl-2-pyrrolidinyl)methyl]-2-hydroxy-6-methoxy-3-tri-butylbenzamide 

Relevant academic research and scientific papers

Silver(I)-catalyzed iodination of arenes: Tuning the lewis acidity of N-iodosuccinimide activation

A mild and rapid method for the iodination of arenes that utilizes silver(I) triflimide as a catalyst for activation of N-iodosuccinimide has been developed. The transformation was found to be general for a wide range of anisole, aniline, acetanilide, and phenol derivatives and allowed the late-stage iodination of biologically active compounds such as PIMBA, a SPECT imaging agent of breast cancer, and (a?)-IBZM, a dopamine D2 receptor antagonist. The method was also modified for the radioiodination of arenes using a one-pot procedure involving the in situ generation of [125I]-N-iodosuccinimide followed by the silver(I)-catalyzed iodination.

Highly Regioselective Iodination of Arenes via Iron(III)-Catalyzed Activation of N-Iodosuccinimide

An iron(III)-catalyzed method for the rapid and highly regioselective iodination of arenes has been developed. Use of the powerful Lewis acid, iron(III) triflimide, generated in situ from iron(III) chloride and a readily available triflimide-based ionic liquid allowed activation of N-iodosuccinimide (NIS) and efficient iodination under mild conditions of a wide range of substrates including biologically active compounds and molecular imaging agents.

RADIOTRACER PRECURSOR AND METHOD FOR PREPARING THE SAME

A precursor SnBZM for a dopamine receptor radiotracer and a method for preparing the same are revealed. The precursor includes a tributyltin group (Bu3Sn) that is easy to be replaced. Thus a dopamine receptor radiotracer 123I-IBZM ca

Dopamine D-2 receptor imaging radiopharmaceuticals: Synthesis, radiolabeling, and in vitro binding of (R)-(+)- and (S)-(-)-3-iodo-2-hydroxy-6 methoxy-N-[(1-ethyl-2-pyrrolidinyl)methyl]benzamide

In developing central nervous system (CNS) dopamine D-2 receptor imaging agents, enantiomers, R-(+) and S-(-) isomers, of 3-[125I]iodo-2-hydroxy-6-methoxy-N-[(1-ethyl-2-pyrrolidinyl)methyl]d benzamide, [125I]IBZM, were synthesized, and their in vitro binding characteristics were evaluated in rat striatum tissue preparation. The (S)-(-)-[125I]IBZM showed high specific dopamine D-2 receptor binding (K(d) = 0.43 nM, B(max) = 0.48 pmol/mg of protein). Competition data of various ligands for IBZM binding displayed the following rank order of potency: spiperone > (S)-(-)-IBZM > (+)-butaclamol >> (R)-(+)-IBZM > (S)-(-)-BZM > dopamine > ketanserin > SCH23390 >> propranolol. The results indicate that [125I]IBZM binds specifically to the dopamine D-2 receptor with stereospecificity. The [123I][IBZM is potentially useful as an imaging agent for the investigation of dopamine D-2 receptors in humans.

Potential neuroleptic agents. 3. Chemistry and antidopaminergic properties of substituted 6-methoxysalicylamides

A series of substituted 6-methoxysalicylamides were synthesized from their corresponding 2,6-dimethoxybenzamides by demethylation of one methoxy group with boron tribromide. Substituted 6-methoxysalicylamides having a lipophilic aromatic substituent in the 3-position para with respect to the methoxy group, e.g. a bromo or an iodo atom or an ethyl or a propyl group, and having an (S)-N-(1-alkyl-2-pyrrolidinyl)methyl moiety as the side chain were found to be potent blockers of [3H]spiperone binding in vitro and potent inhibitors of the apomorphine syndrome in the rat. Similar to remoxipride but in contrast to haloperidol, some of the substituted salicylamides show a 10-20 fold separation between the dose that inhibits hyperactivity and that which inhibits stereotypy. It was concluded that, besides the requirement of a lipophilic substitutent in the position para to the methoxy group for antidopamine activity in vivo, the formation of a coplanar six-membered pseudoring involving the amide moiety and the methoxy group is a structural requirement for activity in vitro.