1353995-07-9

Basic information

• Product Name: Benzyl-Methyl-(S)-pyrrolidin-3-yl-aMine
• Synonyms: Benzyl-Methyl-(S)-pyrrolidin-3-yl-aMine;(3S)-N-benzyl-N-methylpyrrolidin-3-amine
• CAS NO: 1353995-07-9
• Molecular Formula: C12H18N2
• Molecular Weight: 190.28472
• Mol File: 1353995-07-9.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Benzyl-Methyl-(S)-pyrrolidin-3-yl-aMine(CAS DataBase Reference)
• NIST Chemistry Reference: Benzyl-Methyl-(S)-pyrrolidin-3-yl-aMine(1353995-07-9)
• EPA Substance Registry System: Benzyl-Methyl-(S)-pyrrolidin-3-yl-aMine(1353995-07-9)

Safety Data

• Hazardous Substances Data: 1353995-07-9(Hazardous Substances Data)

Upstream product

• 862906-27-2 tert-butyl 3-(benzyl(methyl)amino)pyrrolidine-1-carboxylate 
• 177947-77-2 (S)-3-[(Benzyl-methyl-amino)-methyl]-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 199336-82-8 (R)-3-(N-Benzyl-N-methylamino)pyrrolidine-1-carboxylic acid tert-butyl ester 

Relevant articles and documents

TETRAHYDROPYRAN AND THIOPYRAN DERIVATIVES HAVING MULTIMODAL ACTIVITY AGAINST PAIN

The present invention relates to tetrahydropyran derivatives of formula (I) having dual pharmacological activity towards both the sigma (ο) receptor, and the μ-opioid receptor, to processes of preparation of such compounds, to pharmaceutical compositions comprising them, and to their use in therapy, in particular for the treatment of pain.

Synthesis and serotonergic activity of 3-[2-(pyrrolidin-1- yl)ethyl]indoles: Potent agonists for the h5-HT(1D) receptor with high selectivity over the h5-HT(1B) receptor

The design, synthesis, and biological evaluation of a novel series of 3- [2-(pyrrolidin-1-yl)ethyl]-indoles with excellent selectivity for h5-HT(1D) (formerly 5-HT(1Dα)) receptors over h5-HT(1B) (formerly 5-HT(1Dβ)) receptors are described. Clinically effective antimigraine drugs such as Sumatriptan show little selectivity between h5-HT(1D) and h5-HT(1B) receptors. The differential expression of h5-HT(1D) and h5-HT(1B) receptors in neural and vascular tissue prompted an investigation of whether a compound selective for the h5-HT(1D) subtype would have the same clinical efficacy but with reduced side effects. The pyrrolidine 3b was initially identified as having 9-fold selectivity for h5-HT(1D) over h5-HT(1B) receptors. Substitution of the pyrrolidine ring of 3b with methylbenzylamine groups gave compounds with nanomolar affinity for the h5-HT(1D) receptor and 100-fold selectivity with respect to h5-HT(1B) receptors. Modification of the indole 5-substituent led to the oxazolidinones 24a,b with up to 163-fold selectivity for the h5-HT(1D) subtype and improved selectivity over other serotonin receptors. The compounds were shown to be full agonists by measurement of agonist-induced [35S]GTPγS binding in CHO cells expressed with h5-HT receptors. This study suggests that the h5-HT(1D) and h5-HT(1B) receptors can be differentiated by appropriate substitution of the ligand in the region which binds to the aspartate residue and reveals a large binding pocket in the h5-HT(1D) receptor domain which is absent for the h5-HT(1B) receptor. The compounds described herein will be important tools to delineate the role of h5-HT(1D) receptors in migraine.