141393-93-3

Basic information

• Product Name: (S)-α-methyl-N-(1,2,2-trimethylpropylidene)benzenemethanamine
• Synonyms: (S)-α-methyl-N-(1,2,2-trimethylpropylidene)benzenemethanamine
• CAS NO: 141393-93-3
• Molecular Weight: 203.327
• Mol File: 141393-93-3.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (S)-α-methyl-N-(1,2,2-trimethylpropylidene)benzenemethanamine(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-α-methyl-N-(1,2,2-trimethylpropylidene)benzenemethanamine(141393-93-3)
• EPA Substance Registry System: (S)-α-methyl-N-(1,2,2-trimethylpropylidene)benzenemethanamine(141393-93-3)

Safety Data

• Hazardous Substances Data: 141393-93-3(Hazardous Substances Data)

Upstream product

• 75-97-8 3,3-dimethyl-butan-2-one 
• 618-36-0 rac-methylbenzylamine 
• 2627-86-3 (S)-1-phenyl-ethylamine 

Downstream Products

• 3850-30-4 (S)-1,2,2-trimethylpropylamine 
• 141294-38-4 (S,S)-N-(1,2,2-trimethylpropyl)phenylethyl-1-amine α-methylbenzylamine 
• 141294-37-3 Trimethyl-1,2,2-propyl-phenylaethylamin 

Relevant articles and documents

Influence of bulky substituents on histamine H3 receptor agonist/antagonist properties

Novel derivatives of 3-(1H-imidazol-4-yl)propanol were designed on the basis of lead compounds belonging to the carbamate or ether series possessing (partial) agonist properties on screening assays of the histamine H3 receptor. One pair of enantiomers in the series of α-methyl-branched chiral carbamates was stereoselectively prepared in high optical yields. Enantiomeric purity was checked by Mosher amide derivatives of precursors and capillary electrophoresis of the final compounds with trimethyl-β-cyclodextrin as chiral selector, and was determined to be ≥95%. The novel compounds were investigated in various histamine H3 receptor assays in vitro and in vivo. Some compounds displayed partial agonist activity on synaptosomes of rat brain cortex, whereas others exhibited antagonist properties only. Selected compounds were investigated in [125I]iodoproxyfan binding studies on the human histamine H3 receptor and showed high affinity in the nanomolar concentration range. Under in vivo conditions after oral administration to mice, some of the compounds exhibited partial or full agonist activity in the brain at low dosages. The (S)-enantiomer of one pair of chiral carbamates (9) proved to be the eutomer; thus, the (S)-enantiomer was selected for further pharmacological studies. In a peripheral in vivo test model in rats, measuring the level of inhibition of capsaicin-induced plasma extravasation, (S)-9 again proved its high oral agonist potency with full intrinsic activity (ED50 values of 0.07-0.1 mg/kg depending on tissue).