174636-94-3

Basic information

• Product Name: (R)-N2,N2-DIMETHYL-1-PHENYL-1,2-ETHANEDIAMINE
• Synonyms: (R)-N2,N2-DIMETHYL-1-PHENYL-1,2-ETHANEDIAMINE;(R)-N2,N2-Dimethyl-1-phenyl-1,2-ethanediamine 2HCl
• CAS NO: 174636-94-3
• Molecular Formula: C₁₀H₁₆N₂
• Molecular Weight: 164.25
• Mol File: 174636-94-3.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (R)-N2,N2-DIMETHYL-1-PHENYL-1,2-ETHANEDIAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-N2,N2-DIMETHYL-1-PHENYL-1,2-ETHANEDIAMINE(174636-94-3)
• EPA Substance Registry System: (R)-N2,N2-DIMETHYL-1-PHENYL-1,2-ETHANEDIAMINE(174636-94-3)

Safety Data

• Hazardous Substances Data: 174636-94-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(R)-N2,N2-DIMETHYL-1-PHENYL-1,2-ETHANEDIAMINE is used as a key building block for the synthesis of various pharmaceuticals. Its application is due to its ability to form the backbone of numerous drugs, contributing to their overall structure and function.
Used in Organic Compounds Synthesis:
In the field of organic chemistry, (R)-N2,N2-DIMETHYL-1-PHENYL-1,2-ETHANEDIAMINE is used as a starting material for the creation of different organic compounds. Its role is attributed to its versatile molecular structure, which can be modified and functionalized to produce a wide array of products.
Used in Medicinal Chemistry:
(R)-N2,N2-DIMETHYL-1-PHENYL-1,2-ETHANEDIAMINE is employed as a crucial component in the design and development of new drugs within medicinal chemistry. Its application is based on its chiral nature, which is essential in determining the biological activity and efficacy of the resulting pharmaceuticals.
Used in Asymmetric Synthesis:
(R)-N2,N2-DIMETHYL-1-PHENYL-1,2-ETHANEDIAMINE is also used in asymmetric synthesis, a technique that allows for the creation of molecules with specific three-dimensional structures. The application of (R)-N2,N2-DIMETHYL-1-PHENYL-1,2-ETHANEDIAMINE in this field is due to its chiral properties, which are critical in controlling the stereochemistry of the synthesized molecules, ultimately influencing their biological activity and potential applications.

Upstream product

• 67341-01-9 (R)-N-(tert-butoxycarbonyl)phenylglycinol 
• 102089-75-8 (-)-(1R)-1-[(1',1'-dimethylethoxycarbonyl)amino]-2-(methylsulfonyl)oxy-1-phenylethane 
• 56613-80-0 D-2-phenylglycinol 
• 224633-14-1 (R)-N-(tert-butoxycarbonyl)-α-(dimethylaminomethyl)benzylamine 

Downstream Products

• 1229900-82-6 (4S,5RS,6R)-2-(acetoxymethyl)-6-(3-((R)-2-(dimethylamino)-1-phenylethyl)thioureido)tetrahydro-2H-pyran-3,4,5-triyl triacetate 

Relevant articles and documents

Discovery of a novel class of selective non-peptide antagonists for the human neurokinin-3 receptor. 2. Identification of (S)-N-(1-phenylpropyl)-3- hydroxy-2-phenylquinoline-4-carboxamide (SB 223412)

Optimization of the previously reported 2-phenyl-4-quinolinecarboxamide NK-3 receptor antagonist 14, with regard to potential metabolic instability of the ester moiety and affinity and selectivity for the human neurokinin-3 (hNK-3) receptor, is described. The ester functionality could be successfully replaced by the ketone (31) or by lower alkyl groups (Et, 21, or n-Pr, 24). Investigation of the substitution pattern of the quinoline ring resulted in the identification of position 3 as a key position to enhance hNK-3 binding affinity and selectivity for the hNK-3 versus the hNK-2 receptor. All of the chemical groups introduced at this position, with the exception of halogens, increased the hNK-3 binding affinity, and compounds 53 (3-OH, SB 223412, hNK- 3-CHO binding K(i) = 1.4 nM) and 55 (3-NH2, hNK-3-CHO binding K(i) = 1.2 nM) were the most potent compounds of this series. Selectivity studies versus the other neurokinin receptors (hNK-2-CHO and hNK-1-CHO) revealed that 53 is about 100-fold selective for the hNK-3 versus hNK-2 receptor, with no affinity for the hNK-1 at concentrations up to 100 μM. In vitro studies demonstrated that 53 is a potent functional antagonist of the hNK-3 receptor (reversal of senktide-induced contractions in rabbit isolated iris sphincter muscles and reversal of NKB-induced Ca2+ mobilization in CHO cells stably expressing the hNK-3 receptor), while in vive this compound showed oral and intravenous activity in NK-3 receptor-driven models (senktide-induced behavioral responses in mice and senktide-induced miosis in rabbits). Overall, the biological data indicate that (S)-N-(1-phenylpropyl)-3-hydroxy- 2-phenylquinoline-4-carboxamide (53, SB 223412) may serve as a pharmacological tool in animal models of disease to assess the functional and pathophysiological role of the NK-3 receptor and to establish therapeutic indications for non-peptide NK-3 receptor antagonists.

3-[3-(piperidin-1-yl)propyl]indoles as highly selective h5-HT(1D) receptor agonists

Several 5-HT(ID/1B) receptor agonists are now entering the marketplace as treatments for migraine. This paper describes the development of selective h5-HT(1D)receptor agonists as potential antimigraine agents which may produce fewer side effects. A series of 3-[3-(piperidin-1-yl)propyl]indoles has been synthesized which has led to the identification of 80 (L-772,405), a high- affinity h5-HT(1D) receptor full agonist having 170-fold selectivity for h5- HT(1D) receptors over h5-HT(1B) receptors. L-772,405 also shows very good selectivity over a range of other serotonin and nonserotonin receptors and has excellent bioavailability following subcutaneous administration in rats. It therefore constitutes a valuable tool to delineate the role of h5-HT(1D) receptors in migraine. Molecular modeling and physical properties have been utilized to postulate the binding conformation of these compounds in the receptor cavity.