22263-68-9

Usage

Uses

Used in Pharmaceutical Industry:
Ethyl (S)-2-(1-PhenylethylaMino)acetate is used as a medication for treating low blood pressure during spinal anesthesia, as it helps to increase blood pressure by stimulating the sympathetic nervous system.
Used as a Stimulant:
Ephedrine is used as a stimulant due to its effects on the central nervous system, providing increased alertness and energy.
Used as an Appetite Suppressant:
Ethyl (S)-2-(1-PhenylethylaMino)acetate is used as an appetite suppressant, helping to reduce food intake and promote weight loss.
Used to Improve Athletic Performance:
Ephedrine is used by athletes to enhance performance by increasing energy levels, alertness, and endurance.
Used in Illicit Drug Production:
Although not a legitimate use, Ethyl (S)-2-(1-PhenylethylaMino)acetate is used in the production of illicit drugs such as methamphetamine, which has led to its classification as a controlled substance in many countries.
Due to its potential for abuse and adverse effects, the use of Ethyl (S)-2-(1-PhenylethylaMino)acetate is strictly regulated in various countries to ensure its safe and appropriate application in medical and pharmaceutical settings.

Upstream product

• 2627-86-3 (S)-1-phenyl-ethylamine 
• 105-36-2 ethyl bromoacetate 
• 1381968-65-5 (S)-ethyl 2-(allyl(1-phenylethyl)amino)ethanoate 
• 160865-32-7 (S)-N-allyl-N-(1-phenylethyl)prop-2-en-1-amine 

Downstream Products

• 186586-65-2 [but-3-enyl-((S)-1-phenyl-ethyl)amino]acetic acid ethyl ester 
• 225377-18-4 1,1-dimethylethyl N-(2-ethoxy-2-oxoethyl)-N-<1(S)-phenylethyl>carbamate 
• 211506-85-3 Boc-Phe-(S)-βMeNphe-OEt 
• 799783-05-4 (1'S,3S)-3-methyl-1-(1-phenylethyl)piperazine-2,5-dione 
• 1315564-26-1 (S)-ethyl (2-bromo-N-(1-phenylethyl)acetamido)acetate 
• 1378014-75-5 (S)-ethyl 2-((2-oxopropyl)(1-phenylethyl)amino)acetate 
• 1378014-65-3 2-amino-5-oxo-4-phenyl-7-((S)-1-phenylethyl)-5,6,7,8-tetrahydro-4H-pyrano[2,3-c]pyridine-3-carbonitrile 
• 1378014-79-9 C₂₃H₂₁N₃O₂ 
• 1350815-39-2 (2R,4S)-ethyl 4-methyl-1-((S)-1-phenylethyl)piperidine-2-carboxylate 

Relevant academic research and scientific papers

Diastereoselective approach to cis-4-methyl/thiol-pipecolic esters based on RCM reaction and conjugate michael addition

A synthetic route for the access to enantiopure cis-4-methyl/thiol- pipecolic esters is presented. It is based on the ring-closing metathesis reaction to build the β-unsaturated piperidin-2-one derived from (S)-(-)-phenylethylamine, followed by either diastereoselective conjugate addition of methylorganocuprate allowing access to cis-4-methyl pipecolic ester or by tandem diastereoselective hydrosulforization-thionization reaction providing access to cis-4-thiol pipecolic ethyl esters.

Structure-activity relationship study of selective excitatory amino acid transporter subtype 1 (EAAT1) inhibitor 2-amino-4-(4-methoxyphenyl)-7- (naphthalen-1-yl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile (UCPH-101) and absolute configurational assignment using infrared and vibrational circular dichroism spectroscopy in combination with ab initio hartree-fock calculations

The excitatory amino acid transporters (EAATs) play essential roles in regulating the synaptic concentration of the neurotransmitter glutamate in the mammalian central nervous system. To date, five subtypes have been identified, named EAAT1-5 in humans, and GLAST, GLT-1, EAAC1, EAAT4, and EAAT5 in rodents, respectively. In this paper, we present the design, synthesis, and pharmacological evaluation of seven 7-N-substituted analogues of UCPH-101/102. Analogue 9 inhibited EAAT1 in the micromolar range (IC50 value 20 μM), whereas analogues 8 and 10 were inactive (IC50 values >100 μM). The diastereomeric pairs 11a/11b and 12a/12b were separated by HPLC and the absolute configuration assigned by VCD technique in combination with ab initio Hartree-Fock calculations. Analogues 11a (RS-isomer) and 12b (RR-isomer) inhibited EAAT1 (IC50 values 5.5 and 3.8 μM, respectively), whereas analogues 11b (SS-isomer) and 12a (SR-isomer) failed to inhibit EAAT1 uptake (IC50 values >300 μM).

Direct chemical method for preparing 2,3-epoxyamides using sodium chlorite

A direct method for preparing 2,3-epoxyamides from tertiary allylamines via a tandem C-H oxidation/double bond epoxidation using sodium chlorite is reported. Apparently, the reaction course consists of two steps: (i) allylic oxidation of the starting allylamine to corresponding unsaturated allylamide with sodium chlorite followed by (ii) epoxidation of the allylamide to the 2,3-epoxyamide mediated by hypochlorite ion, which is formed in situ by reduction of sodium chlorite. The reaction conditions tolerate the presence of free hydroxyl groups and typical functional groups such as TBS, aryl, alkyl, allyl, acetyl, and benzyl groups; however, when an activated aromatic ring (e.g., sesamol) is present in the substrate, the use of a scavenger is necessary.

The amide bond rotation controlled by an unusual C- H···O hydrogen bonding that favors the 1,4-phenyl radical migration

Experimental evidence in support of the presence of a weak C-H···O hydrogen bonding that favors 1,4-phenyl radical migration in a chiral amide is provided.

Amino-zinc-enolate carbometalation reactions: Application to ring closure of terminally substituted olefin for the asymmetric synthesis of cis- and trans-3-prolinoleucine

The amino-zinc-enolate cyclization reaction is a straightforward route for the synthesis of 3-substituted prolines. As classical intramolecular carbometalation reactions, the applicability of the addition of zinc to a double bond was limited to a substrat

Discovery of non-peptidic P2-P3 butanediamide renin inhibitors with high oral efficacy

A new series of non-peptidic renin inhibitors having a 2-substituted butanediamide moiety at the P2 and P3 positions has been identified. The optimized inhibitors have IC50 values of 0.8 to 1.4nM and 2.5 to 7.6nM in plasma renin assays at pH 6.0 and 7.4, respectively. When evaluated in the normotensive cynomolgus monkey model, two of the most potent inhibitors were orally active at a dose as low as 3mg/kg. These potent renin inhibitors are characterized by oral bioavailabilities of 40 and 89% in the cynomolgus monkey. Inhibitor 3z (BILA 2157 BS) was selected as candidate for pre-development. Copyright (C) 1999 Elsevier Science Ltd.

New strategy for the synthesis of 3-substituted prolines

Ring formation involving a 5-exo trig cyclization between a zinc enolate and a non activated double bond led to cis diastereoisomer of 3-substituted prolines. This cyclization was achieved with transfer of chirality onto the C-2 carbon when nitrogen was protected by an α-methylbenzyl group. Reprotonation of the lithium enolate of cis derivative yielded the trans diastereoisomer.

Enantioselective Synthesis of (R)- and (S)-α-Aminoacids using (6S)- and (6R)-6-Methyl-morpholine-2,5-dione Derivatives

The alkylation of both 3 and 4 gives exclusively the trans derivatives 5 and 6, respectively, with >98% diastereoselectivity. Cleavage of the morpholine-2,5-dione ring of 5 and 6 leads to enantiomerically pure (S)- and (R)-α-aminoacids, respectively. The configurations of stereogenic centers introduced on 3, 4, 5 and 6 have been assigned on the basis of the 1H-NMR data, conformational analysis and nOe measurements.