14278-49-0

Basic information

• Product Name: N-[3-(4-aminobutylamino)propyl]acetamide
• Synonyms: N-[3-(4-aminobutylamino)propyl]acetamide;N1-Acetylspermidine;N-[3-(Acetylamino)propyl]-1,4-butanediamine
• CAS NO: 14278-49-0
• Molecular Formula: C₉H₂₁N₃O
• Molecular Weight: 187.28
• Mol File: 14278-49-0.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 380.5°Cat760mmHg
• Flash Point: 183.9°C
• Appearance: /
• Density: 0.957g/cm³
• Vapor Pressure: 5.42E-06mmHg at 25°C
• Refractive Index: 1.469
• CAS DataBase Reference: N-[3-(4-aminobutylamino)propyl]acetamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-[3-(4-aminobutylamino)propyl]acetamide(14278-49-0)
• EPA Substance Registry System: N-[3-(4-aminobutylamino)propyl]acetamide(14278-49-0)

Safety Data

• Hazardous Substances Data: 14278-49-0(Hazardous Substances Data)

Usage

InChI:InChI=1/C9H21N3O/c1-9(13)12-8-4-7-11-6-3-2-5-10/h11H,2-8,10H2,1H3,(H,12,13)

Upstream product

• 126993-29-1 {4-[(3-Acetylamino-propyl)-tert-butoxycarbonyl-amino]-butyl}-carbamic acid tert-butyl ester 
• 14464-29-0 N-acetoxysuccinimide 
• 124-20-9 N-(3-aminopropyl)-1,4-diaminobutane 
• 85681-30-7 Toluene-4-sulfonic acid; compound with 4-(tetrahydro-pyrimidin-1-yl)-butylamine 
• 73453-98-2 1-(4-aminobutyl)-1,2,3,4,5,6-hexahydropyrimidine 
• 85681-31-8 1-[3-(4-Amino-butyl)-tetrahydro-pyrimidin-1-yl]-ethanone 

Downstream Products

• 109-76-2 Trimethylenediamine 
• 82414-35-5 N¹,N³-spermidinebis(acetamide) 

Relevant articles and documents

Unexpected Acetylation of Endogenous Aliphatic Amines by Arylamine N-Acetyltransferase NAT2

N-Acetyltransferases play critical roles in the deactivation and clearance of xenobiotics, including clinical drugs. NAT2 has been classified as an arylamine N-acetyltransferase that mainly converts aromatic amines, hydroxylamines, and hydrazines. Herein, we demonstrate that the human arylamine N-acetyltransferase NAT2 also acetylates aliphatic endogenous amines. Metabolomic analysis and chemical synthesis revealed increased intracellular concentrations of mono- and diacetylated spermidine in human cell lines expressing the rapid compared to the slow acetylator NAT2 phenotype. The regioselective N8-acetylation of monoacetylated spermidine by NAT2 answers the long-standing question of the source of diacetylspermidine. We also identified selective acetylation of structurally diverse alkylamine-containing drugs by NAT2, which may contribute to variations in patient responses. The results demonstrate a previously unknown functionality and potential regulatory role for NAT2, and we suggest that this enzyme should be considered for re-classification.

Facile synthesis of monoacetylated spermidines, illustrating selective deacetylation and application of a common precursor.

The synthesis of all three monoacetylated spermidines is reported. N4-Acetylspermidine was obtained in four steps from spermidine via the triacetylated intermediate by selective deacetylation after exhaustive t-butoxycarbonylation as well as directly from