90-81-3

Basic information

• Product Name: racephedrine
• Synonyms: racephedrine;(R*,S*)-(.+-)-alpha-[1-(methylamino)ethyl]benzyl alcohol;(+-)-α-Hydroxy-β-methylaminopropylbenzene;(R*,S*)-α-[1-(Methylamino)ethyl]benzenemethanol;Benzenemethanol, α-[(1R)-1-(methylamino)ethyl]-, (αS)-rel-;Benzenemethanol, α-[1-(methylamino)ethyl]-, (R*,S*)-;Benzenemethanol, α-[1-(methylamino)ethyl]-, (R*,S*)-(+-)-;DL-Ephedrine
• CAS NO: 90-81-3
• Molecular Formula: C₁₀H₁₅NO
• Molecular Weight: 165.2322
• EINECS: 202-017-0
• Mol File: 90-81-3.mol
• Article Data: 11

Chemical Properties

• Melting Point: 75°
• Boiling Point: 293.09°C (rough estimate)
• Flash Point: 85.6 °C
• Appearance: /
• Density: 1.1220
• Refractive Index: 1.4820 (estimate)
• PKA: 13.96±0.20(Predicted)
• CAS DataBase Reference: racephedrine(CAS DataBase Reference)
• NIST Chemistry Reference: racephedrine(90-81-3)
• EPA Substance Registry System: racephedrine(90-81-3)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 26-36
• Hazardous Substances Data: 90-81-3(Hazardous Substances Data)

Usage

Description

Racephedrine is a crystalline compound that is soluble in water, alcohol, chloroform, and oils. It is used in medicine, including in the form of its hydrochloride and sulfate salts.

Uses

Used in Pharmaceutical Industry:
Racephedrine is used as an active pharmaceutical ingredient for its stimulant and decongestant properties. It helps to relieve nasal congestion and can also be used to treat conditions such as asthma and allergies.
Used in Medicine (as hydrochloride and sulfate):
Racephedrine hydrochloride and racephedrine sulfate are used as pharmaceutical agents for their therapeutic effects. They can be formulated into various dosage forms, such as tablets, capsules, and syrups, for easy administration and improved patient compliance.

InChI:InChI=1S/C10H15NO/c1-8(11-2)10(12)9-6-4-3-5-7-9/h3-8,10-12H,1-2H3/t8-,10-/m0/s1

Upstream product

• 95994-95-9 ephedrine methyl ether 
• 299-42-3 ephedrine 
• 321-98-2 (1S,2R)-(+)-ephedrine 
• 124-41-4 sodium methylate 
• 90-82-4 pseudoephedrine 
• 5650-44-2 methcathinone 
• 90-82-4 rac-pseudoephedrine 
• 6402-25-1 (α-methylamino-ethyl)-(4-amino-phenyl)-carbinol 
• 74-89-5 methylamine 
• 579-07-7 1-Phenylpropane-1,2-dione 
• 110505-04-9 N-Nitrosomethylamino-2-propiophenone 
• 7647-01-0 hydrogenchloride 
• 64-17-5 ethanol 
• 6317-31-3 3,4-dimethyl-5-phenyl-2-oxo-1,3-oxazolidine 

Downstream Products

• 90-86-8 (1RS:2SR)-2-(methyl-trans-cinnamyl-amino)-1-phenyl-propanol-⁽¹⁾ 
• 112532-00-0 (1S,2R)-(-)-ephedrinium (S)-(+)-mandelate 
• 42510-95-2 N-((1RS,2RS)-2-hydroxy-1-methyl-2-phenyl-ethyl)-N-methyl-urea 
• 5650-44-2 methcathinone 
• 42511-08-0 (+/-)-hexahydro-pseudoephedrine 
• 90-81-3 ephedrine 
• 25394-33-6 ((1RS,2SR)-2-chloro-1-methyl-2-phenyl-ethyl)-methyl-amine 
• 6402-25-1 (1RS:2RS)-2-methylamino-1-(4-amino-phenyl)-propanol-⁽¹⁾ 
• 7770-92-5 (-)-pseudoephedrine; D_g-hydrogentartrate 
• 299-42-3 ephedrine 
• 321-98-2 (1S,2R)-(+)-ephedrine 
• 42511-08-0 (1RS,2SR)-1-cyclohexyl-2-methylamino-propan-1-ol 
• 6317-31-3 (4RS,5SR)-3,4-dimethyl-5-phenyloxazolidin-2-one 
• 29843-09-2 (+/-)-3,4r-dimethyl-2#x,5t-diphenyl-oxazolidine 

Relevant articles and documents

BIOCATALYTICAL PROCESS FOR RACEMIZATION OF D-EPHEDRINE

This invention relates to methods for racemization of dextro-rotatory ephedrine via enzymatic kinetic conversion, and is particularly useful for conversion of dextro- rotatory ephedrine (d- ephedrine) to racemic mixture of dextro-rotatory ephedrine (d-ephedrine) and levo-rotatory ephedrine (l-ephedrine) to recover the levo-rotatory ephedrine that exhibit potential bronchodilatory and anti-hypotensive activities. The process provides a suspension of Rhizopus Oryzae fungi pellets in diammonium phosphate buffer having pH in the range of pH 5 to 9 and effective sonication to extract specific enzymes for inversion of functional groups present on the chiral carbon atom of d-ephedrine molecule at low temperature which has advantages of working at lower temperature range (20 to 50 °C), lower energy consumption, lesser formation of by-products.

Diastereoselective reduction of α-aminoketones: Synthesis of anti- and syn-β-aminoalcohols

Reduction of N-t-BOC-protected-N-alkyl α-aminoketones with LiEt 3BH or Li(S-Bu)3BH furnishes protected syn-β-aminoalcohols with high selectivities. In contrast, removal of the BOC group followed by reduction of the aminoketone gives anti-β- aminoalcohols with variable selectivities. With aromatic ketones, selectivities are typically high while aliphatic ketones show mediocre to high selectivities depending on steric considerations.

Synthesis of syn- and anti-1,2-amino alcohols by regioselective ring opening reactions of cis-3-aminooxetanes

N-t-Butyloxycarbonyl (Boc) substituted cis-2-phenyl-3-aminooxetanes 3 undergo a ring expansion to oxazolidinones 5 upon treatment with trifluoroacetic acid. The reaction occurs at the C(2) position under inversion of configuration. Alternatively, 3-aminooxetanes can be ring-opened at the less substituted C(4) position with retention of the relative configuration between C(2) and C(3) as exemplified by the synthesis of (+)-pseudoephedrine (2). The cis3-aminooxetanes serve as precursors for either syn- or anti-1,2-amino alcohols.