478-73-9

Usage

Uses

Used in Pharmaceutical Industry:
Pseudococaine is used as a potential local anesthetic and analgesic for its similar pharmacological effects to cocaine. It is being studied for its potential to provide pain relief and numbness in medical procedures, with the advantage of having a lower risk of abuse and addiction compared to traditional cocaine.
Used in Research and Development:
Pseudococaine is used as a research compound to further understand its pharmacological properties and explore its potential medical applications. It serves as a valuable tool for scientists to investigate the mechanisms of action and safety profile of methyl (1R,2S,3S,5S)-3-benzoyloxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate Pseudococaine, as well as to compare its effects with those of cocaine.

InChI:InChI=1/C17H21NO4/c1-18-12-8-9-13(18)15(17(20)21-2)14(10-12)22-16(19)11-6-4-3-5-7-11/h3-7,12-15H,8-10H2,1-2H3/t12-,13+,14-,15-/m0/s1

Upstream product

• 50-36-2 (+/-)-pseudococaine 
• 98-88-4 benzoyl chloride 
• 1393359-57-3 tert-butyl (1R,2S,3R,4R,5S)-3-hydroxy-4-iodo-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate 
• 1393359-56-2 tert-butyl (1R,2S,3S,5S)-3-hydroxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate 
• 38969-40-3 methyl (1R,2S,3S,5S)-3-hydroxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate hydrochloride 
• 65913-90-8 pseudoecgonine methyl ester 
• 93-97-0 benzoic acid anhydride 

Downstream Products

• 484-93-5 ecgonidine 
• 65913-90-8 methyl (1R,2S,3S,5S)-3-hydroxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate 
• 60305-56-8 (1R)-3exo-benzoyloxy-tropane-2endo-carboxylic acid 
• 65-85-0 benzoic acid 
• 481-38-9 (+)-pseudoecgonine 
• 53-21-4 Pseudococaine hydrochloride 
• 112574-75-1 (S)-pseudoecgonine methyl ester 
• 137360-14-6 C₁₇H₁₉NO₅ 

Relevant academic research and scientific papers

Asymmetric synthesis of the tropane alkaloid (+)-pseudococaine via ring-closing iodoamination

Ring-closing iodoamination of tert-butyl 2-hydroxy-7-[N-methyl-N-(α- methyl-p-methoxybenzyl)amino]cyclohept-3-ene-1-carboxylates proceeds with concomitant loss of the N-α-methyl-p-methoxybenzyl group to give the corresponding 8-azabicyclo[3.2.1]octane sca

Two-carbon bridge substituted cocaines: Enantioselective synthesis, attribution of the absolute configuration and biological activity of novel 6- and 7-methoxylated cocaines

In an effort to learn more about the general structure-activity relationships of cocaine with the aim to elucidate those structural features that might confer antagonistic properties to such analogues, we describe herein our synthetic efforts to prepare two-carbon bridge functionalized (methoxylated and hydroxylated) analogues. Our approach makes use of a modification of the classical Willstatter synthesis of cocaine: Mannich type cyclization of acetonedicarboxylic acid monomethyl ester with methylamine hydrochloride and 2-methoxysuccindialdehyde in a citrate buffer solution afforded the 6- and 7-substituted 2-carbomethoxy-3-tropinones 3a,b and 4a,b in approximate yields of 64%. Reduction of the (±)-tropinone derivatives was performed with sodium amalgam in a sulfuric acid solution to afford a mixture of (±)-methoxyecgonine and (±)-methoxypseudoecgonine derivatives 5, 11 and 6, 7, 12, 13. Benzoylation of these alcohols yielded the desired cocaine and pseudococaine-like compounds 8, 14 and 9, 10, 15, 16. Additionally, we show that enzymatic hydrolysis of these cocaine analogues using pig liver esterase (PLE) affords a practical means for achieving their chemical resolution. The enantiomers of the methoxycocaine analogues were also prepared starting from chiral (±)- and(-)-6-methoxytropinone. All new analogues were examined for their ability to displace [3H]mazindol binding and to inhibit high-affinity uptake of [3H]dopamine into striatal nerve ending (synaptosomes). It appeared evident that methoxylation of the cocaine two-carbon bridge provides compounds of particular interest: the K(i) for the binding of the methoxypseudococaines is about two to four times smaller than the K(i) for inhibition of dopamine uptake, thus enabling these compounds capable of countering the effects of cocaine to some extent.

A PLE-based resolution of cocaine, pseudococaine, and 6-and 7-methoxylated cocaine analogues

The enzymatic hydrolysis of racemic cocaine and cocaine analogues using pig liver esterase (PLE) is shown to afford a practical means for achieving their chemical resolution. This reaction was found to proceed not only with good enantioselectivity, but with an interesting chemoselectivity as well.

Syntheses and Conformational Analyses of Isomeric Cocaines: A Proton and Carbon-13 Nuclear Magnetic Resonance Study

The 1H and 13C NMR spectra of cocaine (1), pseudococaine (2), allococaine (3), allopseudococaine (4), and the hydrochloride salts of 1, 2, and 4 have been recorded.The conformation of the piperidine ring in all four isomers, including the orientation of the N-methyl substituent, was determined from analysis of the data.Vicinal, geminal, and long-range coupling constants strongly suggest a chair conformation for the piperidine ring of all the compounds studied.Comparison of the 1H and 13C chemical shift data suggests that 2 and 4 have a larger population of axial N-methyl substituents than 1 and 3, respectively.Improved procedures for the synthesis of 2, 3, and 4 are reported.In particular, a stereoselective route to 4 is presented.