144163-44-0

Basic information

• Product Name: (2S,3S,5S)-2,5-diamino-1,6-diphenylhexan-3-ol
• Synonyms: (2S,3S,5S)-2,5-diamino-3-hydroxy-1,6-diphenylhexane
• CAS NO: 144163-44-0
• Molecular Formula: C₁₈H₂₄N₂O
• Molecular Weight: 284.396
• Mol File: 144163-44-0.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 484.221°C at 760 mmHg
• Flash Point: 246.648°C
• Density: 1.115g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.601
• CAS DataBase Reference: (2S,3S,5S)-2,5-diamino-1,6-diphenylhexan-3-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3S,5S)-2,5-diamino-1,6-diphenylhexan-3-ol(144163-44-0)
• EPA Substance Registry System: (2S,3S,5S)-2,5-diamino-1,6-diphenylhexan-3-ol(144163-44-0)

Safety Data

• Hazardous Substances Data: 144163-44-0(Hazardous Substances Data)

Usage

Description

(2S,3S,5S)-2,5-diamino-1,6-diphenylhexan-3-ol, also known as ephedrine, is a natural alkaloid compound found in plants of the Ephedra genus. It is a psychoactive substance with a chemical structure that includes two amine groups and a phenyl ring, contributing to its bioactivity and medicinal properties. Ephedrine has been used for centuries in traditional Chinese medicine as a decongestant and bronchodilator, as well as a stimulant, appetite suppressant, and weight loss aid.

Uses

Used in Pharmaceutical Industry:
Ephedrine is used as a pharmaceutical compound for its effects on the central nervous system and cardiovascular system. Its medicinal properties make it valuable in the development of drugs, although its use is strictly controlled due to the potential for abuse and adverse effects.
Used in Traditional Chinese Medicine:
Ephedrine has been used for centuries in traditional Chinese medicine as a decongestant and bronchodilator, helping to relieve nasal congestion and improve breathing.
Used as a Stimulant:
Ephedrine is used as a stimulant to increase alertness and energy levels, although its use in this capacity is regulated due to potential for misuse and abuse.
Used as an Appetite Suppressant and Weight Loss Aid:
Ephedrine has been used to suppress appetite and aid in weight loss, although its use for this purpose is also regulated due to potential adverse effects and the risk of misuse.

Upstream product

• 144163-85-9 (2S,3S,5S)-2-amino-3-hydroxy-5-(t-butyloxycarbonylamino)-1,6-diphenylhexane 
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• 331766-97-3 tert-butyl (1S,2R,4R)-1-benzyl-2,4-dihydroxy-5-phenylpentylcarbamate 
• 331766-98-4 Methanesulfonic acid (R)-1-benzyl-2-((4S,5S)-4-benzyl-2-oxo-oxazolidin-5-yl)-ethyl ester 
• 331766-99-5 (4S,5S)-4-benzyl-5-[(2S)-2-azido-3-phenylpropyl]-1,3-oxazolidin-2-one 
• 198208-08-1 (4R,5S)-5-[N-(tert-butyloxycarbonyl)amino]-4-hydroxy-1,6-diphenyl-2-hexene 
• 198208-15-0 (2R,3R,4S,5S)-5-[N-(tert-butyloxycarbonyl)amino]-2,3-epoxy-4-hydroxy-1,6-diphenylhexane 

Downstream Products

• 144163-88-2 ((1S,2S,4S)-4-amino-1-benzyl-2-hydroxy-5-phenyl-pentyl)-carbamic acid tert-butyl ester 
• 144164-11-4 (2S,3S,5S)-5-Amino-2-(N-((5-thiazolyl)-methoxycarbonyl)amino)-3-hydroxy-1,6-diphenylhexane 
• 165315-39-9 (4S,6S,1'S)-6-(1-amino-2-phenylethyl)-4-benzyl-2-phenyl-3-aza-2-bora-1-oxacyclohexane 
• 220784-30-5 allyl 10-<1'-<<(2''S,3''S,5''S)-2'',5''-bis<(fluorenylmethyloxycarbonyl)amino>-1'',5''-diphenylhex-3''-yl>oxy>ethoxy>decanoate 
• 220784-31-6 10-<1'-<<(2''S,3''S,5''S)-2'',5''-bis<(fluorenylmethyloxycarbonyl)amino>-1'',5''-diphenylhex-3''-yl>oxy>ethoxy>decanoic acid 

Relevant articles and documents

New Active HIV-1 Protease Inhibitors Derived from 3-Hexanol: Conformation Study of the Free Inhibitors in Crystalline State and in Complex with the Enzyme

Four novel linear non-peptidic HIV-1 protease inhibitors derived from 2,5-diamino-1,6-diphenyl-3-hexanol were synthesized and characterized. All of them exhibit tight binding to HIV-1 protease, with inhibition constants Ki in the range 20pm-5nm. The investigated inhibitors were crystallized, and their crystal structures were determined by X-ray diffraction. In all cases, the conformations found in the crystalline state differ significantly from the conformations obtained by computational docking of the inhibitor in the binding cleft of native HIV-1 protease. Owing to the prevalence of hydrophobic substituents in all these inhibitors, the conformational mobility in water solution is restricted to their compact forms. The spectrum of low-energy conformations in solution dramatically changes during the formation of inhibitor crystals (phenyl ring stacking as a leading motif) or during the formation of a complex with HIV-1 protease (elongated conformation suitable to fit the enzyme pockets as a factor responsible for tight binding). High conformational flexibility and low conformational stress in the molecules of these inhibitors most likely increase their biological activity in comparison with more rigid compounds.

Small hydroxyethylene-based peptidomimetics inhibiting both HIV-1 and C. albicans aspartic proteases

We have extended a highly flexible method for rapidly assembling aspartic protease inhibitors to produce symmetric and asymmetric monohydroxyethylene peptidomimetics. This method is based on the prior synthesis of the central non-cleavable peptide-bond is

Pharmaceutical composition for inhibiting HIV protease

A pharmaceutical composition is disclosed which comprises a solution of an HIV protease inhibiting compound in a pharmaceutically acceptable organic solvent comprising a mixture of (1) (a) a solvent selected from propylene glycol and polyethylene glycol or (b) a solvent selected from polyoxyethyleneglycerol triricinoleate, polyethylene glycol 40 hydrogenated castor oil, fractionated coconut oil, polyoxyethylene (20) sorbitan monooleate and 2-(2-ethoxyethoxy)ethanol or (c) a mixture thereof and (2) ethanol or propylene glycol.