55727-59-8

Usage

Uses

Used in Recreational Drug Industry:
2-Pyrrolidin-1-ylmethyl-phenylamine is used as a recreational drug for its hallucinogenic and euphoric properties. However, its use can lead to serious health risks and potential dependence, making it a controlled substance in many countries.

InChI:InChI=1/C11H16N2/c12-11-6-2-1-5-10(11)9-13-7-3-4-8-13/h1-2,5-6H,3-4,7-9,12H2

Upstream product

• 495-58-9 1,2,3,3a,4,9-hexahydropyrrolo<2,1-b>quinazoline 
• 39101-28-5 2,3--3,4-dihydroquinazoline 
• 530-53-0 deoxyvasicinone 
• 55581-63-0 1-(2-nitro-benzyl)-pyrrolidine 
• 495-59-0 deoxypeganine 
• 7664-93-9 sulfuric acid 
• 500896-60-6 N-(2-amino-benzyl)-succinimide 
• 1904-78-5 2-nitrobenzylamine 
• 39101-27-4 N-(o-nitrobenzyl)-succinimide 
• 872277-54-8 N-(2-amino-benzyl)-succinamic acid 
• 876492-92-1 N-(2-nitro-benzyl)-succinamic acid 
• 612-23-7 2-nitrobenzyl chloride 
• 6159-55-3 (+)-vasicinol 
• 552-89-6 2-nitro-benzaldehyde 

Relevant academic research and scientific papers

Synthetic analogs of Peganum alkaloids VIII. A quantum-mechanical investigation of the reduction of deoxypeganine and its derivatives

The alkaloid deoxypeganine and some of its derivatives have been subjected to reduction with sodium tetrahydroborate and with the complex NaBH4·BF3·Et2O. It has been shown that the structures of the reduction products depend on the presence and positions of substituent s in the benzene ring. The quantum-chemical calculations performed have confirmed the probable formation of reduced structures of the type of o-aminobenzylpyrrolidine and the type of a macrocyclic diamine.

Redox Condensations of o-Nitrobenzaldehydes with Amines under Mild Conditions: Total Synthesis of the Vasicinone Family

A total synthesis of the vasicinone family of natural products from bulk chemicals was developed. Reductive condensation of o-nitrobenzaldehydes with amines utilizing iron pentacarbonyl as a reducing agent followed by subsequent oxidation leads to a great variety of polycyclic nitrogen-containing heterocycles under mild conditions. Enantiomerically pure vasicinone, rutaecarpine, isaindigotone, and luotonin were synthesized from readily available starting materials like hydroxyproline, nitrobenzaldehyde, pyrrolidine, and piperidine in two to four operational steps without chromatography. The antifungal activity of all products was tested.

Natural (-)-vasicine as a novel source of optically pure 1-benzylpyrrolidin-3-ol

A facile and scalable methodology for the preparation of optically active (3S)-1-benzylpyrrolidin-3-ol (3), an important drug precursor, is reported. Starting from the naturally occurring alkaloid (-)-vasicine (1), a major alkaloid of the plant Adhatoda vasica, 3 was obtained in 84% overall yield (Scheme 3). Copyright