67198-19-0

Basic information

• Product Name: N-Methyl-N-[(1S,2S)-2-pyrrolizinocyclohexyl]-2-(3,4-dichlorophenyl)acetamide
• Synonyms: N-Methyl-N-[(1S,2S)-2-pyrrolizinocyclohexyl]-2-(3,4-dichlorophenyl)acetamide
• CAS NO: 67198-19-0
• Molecular Formula: C₁₉H₂₆Cl₂N₂O
• Molecular Weight: 369.33
• Mol File: 67198-19-0.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 496.6°C at 760 mmHg
• Flash Point: 254.1°C
• Appearance: /
• Density: 1.23±0.1 g/cm3(Predicted)
• Vapor Pressure: 5.35E-10mmHg at 25°C
• Storage Temp.: Desiccate at RT
• PKA: 9.21±0.20(Predicted)
• CAS DataBase Reference: N-Methyl-N-[(1S,2S)-2-pyrrolizinocyclohexyl]-2-(3,4-dichlorophenyl)acetamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-Methyl-N-[(1S,2S)-2-pyrrolizinocyclohexyl]-2-(3,4-dichlorophenyl)acetamide(67198-19-0)
• EPA Substance Registry System: N-Methyl-N-[(1S,2S)-2-pyrrolizinocyclohexyl]-2-(3,4-dichlorophenyl)acetamide(67198-19-0)

Safety Data

• Hazardous Substances Data: 67198-19-0(Hazardous Substances Data)

Usage

Biological Activity

More active enantiomer of (±)-U-50488 (trans-(?-3,4-Dichloro-N-methyl-N-[2-(1-pyrrolidinyl)cyclohexyl]benzeneacetamide hydrochloride ).

InChI:InChI=1/C19H26Cl2N2O.ClH/c1-22(19(24)13-14-8-9-15(20)16(21)12-14)17-6-2-3-7-18(17)23-10-4-5-11-23;/h8-9,12,17-18H,2-7,10-11,13H2,1H3;1H/t17-,18-;/m0./s1

Upstream product

• 67198-34-9 trans-(+/-)-N-methyl-2-(pyrrolidin-1-yl)cyclohexanamine 
• 6831-55-6 2-(3,4-dichlorophenyl)acetyl chloride 
• 824938-84-3 benzyl (1S,2S)-N-[2-(pyrrolidin-1-yl)cyclohexyl]carbamate 
• 67198-53-2 trans-N-methyl-2-(1-pyrrolidinyl)-cyclohexanamine 
• 137858-60-7 2-(N-t-butyloxycarbonyl-N-methylamino)cyclohexanone 
• 20431-81-6 rac-trans-2-methylamino-cyclohexanol 
• 5807-30-7 3,4-dichlorophenyl acetic acid 
• 67198-34-9 (+/-)-cis-N-methyl-2-(1-pyrrolidinyl)cyclohexylamine 
• 130993-58-7 Methanesulfonic acid (1R,2R)-2-pyrrolidin-1-yl-cyclohexyl ester 
• 286-20-4 cyclohexane-1,2-epoxide 
• 69420-67-3 (+/-)-trans-[2-(pyrrolidinyl)]cyclohexanol 

Downstream Products

• 67197-96-0 U 50488 hydrochloride 
• 135211-16-4 (1R,2R)-(-)-trans-N-<2-(3,4-dichlorophenyl)ethyl>-N-methyl-2-(1-pyrrolidinyl)cyclohexylamine 
• 135211-17-5 (1S,2S)-(+)-trans-N-<2-(3,4-dichlorophenyl)ethyl>-N-methyl-2-(1-pyrrolidinyl)cyclohexylamine 

Relevant articles and documents

Optimisation of the Anti-Trypanosoma brucei Activity of the Opioid Agonist U50488

Screening of the Sigma-Aldrich Library of Pharmacologically Active Compounds (LOPAC) against cultured Trypanosoma brucei, the causative agent of African sleeping sickness, resulted in the identification of a number of compounds with selective antiproliferative activity over mammalian cells. These included (+)-(1R,2R)-U50488, a weak opioid agonist with an EC50 value of 59nM as determined in our T.brucei invitro assay reported previously. This paper describes the modification of key structural elements of U50488 to investigate structure-activity relationships (SAR) and to optimise the antiproliferative activity and pharmacokinetic properties of this compound.

Chemoenzymatic preparation of optically active trans-cyclohexane-1,2- diamine derivatives: An efficient synthesis of the analgesic U-(-)-50,488

Stereoespecific syntheses of (±)-trans-N,N-cyclohexane-1,2-diamines ((±)-4a-g) were carried out from the corresponding (±)-trans-N,N- dialkylaminocyclohexanols by successive treatment with mesyl chloride and aqueous ammonia. The stereochemical outcome indicates the formation of a meso-aziridinium ion intermediate, Kinetic resolutions of diamines (±)-4 were efficiently accomplished in aminolysis reactions catalyzed by lipase B from Candida antarctica with ethyl acetate as the solvent and acyl donor. Acetamides and the remaining diamines, isolated as the benzyloxycarbonyl derivatives, were obtained with very high ee values (92-99%), One of the carbamates was used as a precursor of the analgesic U-(-)-50,488.

Benzeneacetamide Amines: Structurally Novel Non-mμ Opioids

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