97635-24-0

Usage

Uses

Used in Recreational Substances:
1-(4-METHYLPHENYL)-3-(1-PYRROLIDINYL)-1& is used as a recreational substance for its euphoric and stimulant effects. It is sought after for its ability to increase dopamine and norepinephrine levels in the brain, resulting in heightened energy, alertness, and a sense of euphoria.
Used in Research and Development:
In the field of pharmaceutical research and development, 1-(4-METHYLPHENYL)-3-(1-PYRROLIDINYL)-1& may be used as a compound of interest for studying its effects on the central nervous system. This can potentially lead to the development of new medications or therapies for various conditions related to the nervous system.
Used in Controlled Substances Regulation:
Due to its classification as a controlled substance in many countries, 1-(4-METHYLPHENYL)-3-(1-PYRROLIDINYL)-1& is used in the enforcement and regulation of drug policies. Authorities may utilize 1-(4-METHYLPHENYL)-3-(1-PYRROLIDINYL)-1& as a reference in the detection, monitoring, and control of its distribution and use to prevent abuse and dependence.

InChI:InChI=1/C14H19NO.ClH/c1-12-4-6-13(7-5-12)14(16)8-11-15-9-2-3-10-15;/h4-7H,2-3,8-11H2,1H3;1H

Upstream product

• 50-00-0 formaldehyd 
• 25150-61-2 pyrrolidine hydrochloride 
• 122-00-9 para-methylacetophenone 
• 123-75-1 pyrrolidine 

Relevant academic research and scientific papers

Investigation of inhibitory properties of some hydrazone compounds on hCA I, hCA II and AChE enzymes

Recently, inhibition of carbonic anhydrase (hCA) and acetylcholinesterase (AChE) have appeared as a promising approach for pharmacological intervention in a variety of disorders such as glaucoma, epilepsy, obesity, cancer, and Alzheimer's disease. Keeping this in mind, N,N′-bis[(1-aryl-3-heteroaryl)propylidene]hydrazine dihydrochlorides, N1-N11, P1, P4-P8, and R1-R6, were synthesized to investigate their inhibitory activity against hCA I, hCA II, and AChE enzymes. All compounds in N, P, and R-series inhibited hCAs (I and II) and AChE more efficiently than the reference compounds acetazolamide (AZA), and tacrine. According to the activity results, the most effective inhibitory compounds were in R-series with the Ki values of 203 ± 55–473 ± 67 nM and 200 ± 34–419 ± 94 nM on hCA I, and hCA II, respectively. N,N′-Bis[1-(4-fluorophenyl)-3-(morpholine-4-yl)propylidene]hydrazine dihydrochlorides, N8, in N-series, N,N′-Bis[1-(4-hydroxyphenyl)-3-(piperidine-1-yl)propylidene]hydrazine dihydrochlorides, P4, in P-series, and N,N′-bis[1-(4-chlorophenyl)-3-(pyrrolidine-1-yl)propylidene]hydrazine dihydrochlorides, R5, in R-series were the most powerful compounds against hCA I with the Ki values of 438 ± 65 nM, 344 ± 64 nM, and 203 ± 55 nM, respectively. Similarly, N8, P4, and R5 efficiently inhibited hCA II isoenzyme with the Ki values of 405 ± 60 nM, 327 ± 80 nM, and 200 ± 34 nM, respectively. On the other hand, P-series compounds had notable inhibitory effect against AChE than the reference compound tacrine and the Ki values were between 66 ± 20 nM and 128 ± 36 nM. N,N′-Bis[1-(4-fluorophenyl)-3-(piperidine-1-yl)propylidene]hydrazine dihydrochlorides, P7, was the most potent compound on AChE with the Ki value of 66 ± 20 nM. The other most promising compounds, N,N′-bis[1-(4-hydroxyphenyl)-3-(morpholine-4-yl)propylidene]hydrazine dihydrochlorides, N4 in N-series and N,N′-bis[1-(4-hydroxyphenyl)-3-(pyrrolidine-1-yl)propylidene]hydrazine dihydrochlorides, R4 in R-series were againts AChE with the Ki values of 119 ± 20 nM, 88 ± 14 nM, respectively.

Cytotoxicities of novel hydrazone compounds with pyrrolidine moiety: inhibition of mitochondrial respiration may be a possible mechanism of action for the cytotoxicity of new hydrazones

N,N’-Bis[1-aryl-3-pyrrolidine-1-yl)propylidene]hydrazine dihydrochlorides (R1–R7) were synthesized by the reaction of 2 mols of 1-aryl-3-(pyrrolidine-1-yl)-1-propanone hydrochlorides with 1 mol of hydrazine hydrate and reported for the first time with their detailed spectral analysis and cytotoxicities towards human hepatoma (Huh7) and breast cancer (T47D) cell lines. Compounds R2, R6, and R7 with the IC50 values of 5.16, 6.96, and 5.96 μM, respectively, showed higher cytotoxic potency than the reference compound 5-FU with 7.0 μM against Huh7 cell line. However, all compounds did not show better cytotoxic activities than 5-FU against T47D cell line at the conditions studied. The representative compound of series, R2, inhibited the mitochondrial respiration at 90, 165, and 265 μM concentrations in a dose dependent manner in liver homogenates, suggesting that mitochondrial respiration may be one of the contributing factor to the cytotoxicity of the compounds synthesized. The compounds R2, R6, and R7 can be chosen as the leader compounds of this study for further studies.

ARALKYL DIAMINE DERIVATIVES AND USES THEREOF AS ANTIDEPRESSANTS

Aralkyl diamine derivative of the following formula, pharmaceutically acceptable salts or uses thereof as antidepressants. The derivatives have triplex inhibiting activities of the reuptake of 5-HT, dopamine and noradrenalin, which can be administered to the patients in need of such treatment in the form of compositions orally or injectedly et al.

Synthesis of hypolipidemic evaluation of β-alkylaminopropiophenone and β-alkylaminopropio-2'-naphthone derivatives in rodents

A series of β-alkylamino-(4'-alkyl)-propiophenone or β-alkylamino(7'-methyl)-propio-2'-naphthone derivatives were prepared and found to have hypolipidemic activity by lowering both serum cholesterol and triglyceride levels in rodents. The electron donating substituent at the para position of the phenyl ring seems to decrease the hypolipidemic activity when compared to non-substituted or electron withdrawing group substituted analogs as investigated previously in this laboratory. In comparison with lovastatin or clofibrate, most of these analogs showed similar or higher activity in lowering both serum cholesterol or triglyceride levels. β-Pyrrolidino-(4'-methyl)-propiophenone (1) demonstrated the best activity after 16 d, i.p. administration in mice at 8 mg/kg/d. Further detailed studies in rats indicated that β-pyrrolidino-(4'-methyl)-propiophenone also showed decreased serum cholesterol and triglyceride levels with increased HDL-cholesterol and triglyceride levels after 14 d. In hyperlipidemic mice and rats, this compound was observed to be effective in lowering serum lipid levels as well as tissue lipid levels. The activities of hepatic acetyl CoA synthetase, phosphatidylate phosphohydrolase, and hepatic lipoprotein lipase were moderately inhibited by β-pyrrolidino-(4'-methyl)-propiophenone.