5250-04-4

Usage

Class

Synthetic stimulant drug

Family

Cathinone class

Structural Relation

Related to MDPV and cathinone derivatives

Action

Selective serotonin-norepinephrine-dopamine reuptake inhibitor (SSNRI)

Usage

Recreational drug

Effects

Stimulant and hallucinogenic

Common Products

Found in "bath salts" or "legal highs"

Regulation

Use and distribution regulated in many countries due to potential for abuse and harmful health effects

Upstream product

• 50-00-0 formaldehyd 
• 10024-89-2 morpholin hydrochloride 
• 122-00-9 para-methylacetophenone 
• 110-91-8 morpholine 
• 5250-02-2 3-(dimethylamino)-4'-methyl propiophenone hydrochloride 

Downstream Products

• 788795-78-8 4-(3-Oxo-3-p-tolyl-propylamino)-benzoic acid 2-diethylamino-ethyl ester 
• 1341192-64-0 2-imino-3-(3-oxo-3-(p-tolyl)propyl)thiazolidin-4-one 

Relevant academic research and scientific papers

Synthesis of 4-(3-oxo-3-phenylpropyl)morpholin-4-ium chloride analogues and their inhibitory activities of nitric oxide production in lipopolysaccharide-induced BV2 cells

Based on our previous report that 3-morpholino-1-phenylpropan-1-one 2, one of the fluoxetine's simplified morpholino analogue, inhibited nitric oxide (NO) production, in this paper, various substituted benzene analogues with morpholine hydrochloride of 2 were synthesized and their inhibitory effects on NO production in lipopolysaccharide (LPS)-induced BV2 cells were tested. Among the synthesized compounds, 2-trifluoromethyl analogue 16n (IC50 = 8.6 μM) showed a significantly higher inhibitory activity than that of the parent compound 2a (IC50 > 50 μM) and suppressed NO production dose-dependently without cytotoxicity. Compound 16n also inhibited iNOS expression in LPS-induced BV2 cells at 2, 10 and 20 μM concentrations. These results suggest that compound 16n inhibited NO production by suppressing the expression of iNOS and can be used as a lead structure for developing new inhibitor of NO production.

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.

Synthesis of mannich bases by two different methods and evaluation of their acetylcholine esterase and carbonic anhydrase inhibitory activities

Background: Mannich bases are an important compounds in medicinal chemistry. They have wide range of biological activities including carbonic anhydrase (CA) inhibitory and acetylcholine esterase inhibitory (AChE) activities. Objective: It was aimed to synthesize Mannich bases, 1-aryl-3-(morpholin-4-yl/piperidin-1-yl)-1- propanone hydrochloride, by microwave irradiation and conventional heating methods to compare the methods in terms of reaction times and yields and to investigate their inhibitory effects on AChE enzyme and CA isoenzymes. Method: Mannich bases were synthesized using conventional heating and microwave irradiation methods under different reaction conditions. Inhibitory effects of the compounds on CA isoenzymes and AChE were evaluated according to literature procedure. Results: IC50 and Ki values of the compounds were evaluated against hCA I, II and AChE. The compounds had more potent or equal Ki values with the references used. Conclusion: This study makes an important contribution to the Mannich base library in terms of synthetic strategy. According to IC50 or Ki values the compounds 6 in Series A with morpholine and and 15 in Series B with piperidine towards both hCA I and/or II isoenzymes and the compounds 4 in Series A and 11, 13, 14, 15, 16, and 18 in Series B towards AChE seemed the leader compounds of the study.

Cytotoxicity of hydrazones of morpholine bearing mannich bases towards Huh7 and T47D cell lines and their effects on mitochondrial respiration

N,N'-bis[1-(substitutedphenyl)-3-(morpholine-4-yl)propylidene]hydrazine dihydrochlorides, N1-N11 were designed and synthesized as cytotoxic agents. These compounds were synthesized by the reaction of 2 moles of 1-(substitutedphenyl)-3-(morpholine-4-yl)-1-propanone hydrochlorides with 1 mole of hydrazine hydrate. The compounds reported here are new, except N1 and N4. The cytotoxicity of the compounds was tested against human hepatoma (Huh7) and breast cancer (T47D) cell lines. 5-Fluorouracil (5-FU) was used as a reference compound. It was found that N3, which has 4-methoxy substituent on phenyl ring, was the most cytotoxic compound towards both cell lines. Its cytotoxicity was 5.6 times higher than 5-FU. Representative compounds N2 at 144, 264 and 424 μM and N3 at 401 μM concentrations significantly inhibited mitochondrial respiration in a dose dependent manner in liver homogenates. This suggests that the inhibition of mitochondrial respiration may be one of the contributing mechanisms to the cytotoxicity of the compounds. N3 may serve as a candidate compound for further studies.

Certain substituted 1-aryl-3-morpholinopropanones to treat Alzheimer's Disease

Disclosed are compounds of formula I: STR1 wherein X is selected from oxygen, sulfur and NR; wherein R is selected from hydrogen, loweralkyl and CH2 CH2 COAr1 ; and Z is hydrogen; straight or branched chain alkyl having 1-

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.