84472-25-3

Basic information

• Product Name: N-Acetyl-(+)-Pseudoephedrine
• Synonyms: N-Acetyl-(+)-Pseudoephedrine
• CAS NO: 84472-25-3
• Molecular Formula: C₁₂H₁₇NO₂
• Molecular Weight: 207.26888
• Mol File: 84472-25-3.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• CAS DataBase Reference: N-Acetyl-(+)-Pseudoephedrine(CAS DataBase Reference)
• NIST Chemistry Reference: N-Acetyl-(+)-Pseudoephedrine(84472-25-3)
• EPA Substance Registry System: N-Acetyl-(+)-Pseudoephedrine(84472-25-3)

Safety Data

• Hazardous Substances Data: 84472-25-3(Hazardous Substances Data)

Usage

Description

N-Acetyl-(+)-Pseudoephedrine is the N-acetylated analogue of the non-selective adrenergic agonist (+)-Pseudoephedrine (P839350). It is a synthetic compound derived from the natural alkaloid ephedrine, which is found in various plant species. The N-acetylation process involves the addition of an acetyl group to the nitrogen atom of the amine group, resulting in a more stable and less reactive molecule compared to its parent compound.

Uses

Used in Pharmaceutical Industry:
N-Acetyl-(+)-Pseudoephedrine is used as a pharmaceutical intermediate for the synthesis of various adrenergic agonist drugs. It serves as a key building block in the production of medications that target the adrenergic receptors, which play a crucial role in the regulation of various physiological processes, such as blood pressure, heart rate, and bronchodilation.
Used in Research Applications:
N-Acetyl-(+)-Pseudoephedrine is utilized as a research tool in the study of adrenergic receptor pharmacology. It helps researchers understand the structure-activity relationships of adrenergic agonists and antagonists, as well as their interactions with different receptor subtypes. This knowledge is essential for the development of more selective and potent drugs with fewer side effects.
Used in Analytical Chemistry:
N-Acetyl-(+)-Pseudoephedrine can be employed as a reference compound in analytical chemistry for the development and validation of methods for the detection and quantification of adrenergic agonists in biological samples. This is particularly relevant in the fields of drug testing, forensic toxicology, and pharmacokinetic studies.

Upstream product

• 67-56-1 methanol 
• 110-96-3 diisobutylamine 
• 1630-34-8 acetic acid-((1S,2S)-2-methylamino-1-phenyl-propyl ester); hydrochloride 
• 67-66-3 chloroform 
• 623-11-0 1-methyl-4-nitrosobenzene 
• 90-82-4 pseudoephedrine 
• 108-24-7 acetic anhydride 
• 18871-66-4 N,N-dimethylacetamide dimethyl acetal 
• 492-39-7 (1S,2S)-2-amino-1-phenylpropanol 
• 145416-68-8 (1S,2S)-N,N-Dimethyl-N'-<(2-hydroxy-2-phenyl)-1-methylethyl>-harnstoff 
• 299-42-3 ephedrine 
• 90-82-4 rac-pseudoephedrine 
• 29724-89-8 N-((1RS,2RS)-2-chloro-1-methyl-2-phenyl-ethyl)-N-methyl-acetamide 
• 90-81-3 ephedrine 

Downstream Products

• 760188-33-8 (1'S,1''S,2''S,4R)-4-{1'-hydroxy-2'-[N-(2''-hydroxy-1''-methyl-2''-phenylethyl)-N-methylcarbamoyl]ethyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 
• 1262432-84-7 N-tert-butoxycarbonyl-(2R)-{1-hydroxy-2-[N-((S,S)-2-phenyl-2-hydroxy-1-methylethyl)-N-methylcarbamoyl]ethyl}pyrrolidine 
• 1262432-88-1 C₂₆H₄₆N₂O₆Si 
• 1262432-79-0 (3S)-3-((4R)-2,2-dimethyl[1,3]dioxolan-4-yl)-3-hydroxy-N-((1S,2S)-1-hydroxy-1-phenylpropan-2-yl)-N-methylpropanamide 
• 1310492-20-6 C₁₇H₂₅NO₄ 
• 1310492-00-2 C₂₀H₂₉NO₄ 
• 1310492-18-2 C₁₉H₂₉NO₃ 
• 1310492-22-8 C₁₆H₂₅NO₃ 

Relevant articles and documents

Application of the Mitsunobu reaction to ephedrines and some related amino alcohols. Aspects of intramolecular participation of the amino group

Inversion of configuration at the benzylic hydroxyl group of (1S,2S)-pseudoephedrine (2) to afford (1R,2S)-ephedrine is known to be a difficult process.The Mitsunobu reactions of 1 and 2 might offer a route to achieve such inversions.In fact Mitsunobu reactions on 1 and 2 are known to proceed via aziridines formed on intramolecular SN2 substitution by the amine functionality.The Mitsunobu reactions of N-methylated and N-benzylated ephedrines have been found to proceed via the corresponding aziridinium ions.These aziridinium ions can be opened (SN2 substitution) by nucleophiles like phthalimide and thiols.Intramolecular participation in 2 can be avoided by use of the tert-butyloxycarbonyl-(BOC) or benzyloxycarbonyl- (CBZ) protected derivatives.Mitsunobu reactions on these derivatives lead to inversion of configuration at the benzylic hydroxyl center.In contrast the BOC and CBZ derivatives of 1 are deprotected under Mitsunobu conditions.The Mitsunobu reactions of threo (1S,2S)-2-amino-1,3-propanediol have also been examined.An attempt to achieve protection by reaction with dimethylformamide dimethyl acetal led to the more substituted 2-oxazoline as established by X-ray crystallography.The desired inversion of configuration of the benzylic hydroxylic group was eventually achieved by protection of the amino substituent as the phthalimide and protection of the primary hydroxyl group as the tosylate.

Reactions of (-)-Ephedrine, (+)-Norpseudoephedrine and Derivatives with N,N-Dimethylacetamid-dimethylacetal and N,N-Dimethylformamid-dimethylacetal

The reactivity of (-)-ephedrine (2) and (+)-norpseudoephedrine (3) towards the amid-acetals 1 a/b has been studied.Both 2 and 3 were acetylated resp. formylated at first at the amino group.Nevertheless, derivatives of 2 and 3 possessing a trisubstituted amino group react with 1 a in a sigmatropic rearrangement to ortho substituted dimethylcarbamoylmethyl derivatives.By subsequent reduction with lithiumaluminiumhydride the aromatic compounds 8, 13, and 18 with two aminoethyl groups are easily available.In contrast to these results 1 b did not furnish any rearrangement products. Keywords. (-)-Ephedrine; (+)-Norpseudoephedrine; N,N-Dimethylacetamid-dimethylacetal; N,N-Dimethylformamid-dimethylacetal; Sympathomimetic effects; Sigmatropic rearrangements.