13431-24-8

Basic information

• Product Name: N(8)-acetylspermidine
• Synonyms: N-(3-Aminopropyl)-N'-acetyl-1,4-butanediamine;N-Acetyl-N'-(3-aminopropyl)-1,4-butanediamine;34450-15-2 (Di-hydrochloride);Acetamide, N-(4-((3-aminopropyl)amino)butyl)-;N(8)-Monoacetylspermidine
• CAS NO: 13431-24-8
• Molecular Formula: C₉H₂₁N₃O
• Molecular Weight: 187.28
• Mol File: 13431-24-8.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 383.2°Cat760mmHg
• Flash Point: 185.5°C
• Appearance: /
• Density: 0.957g/cm³
• Vapor Pressure: 4.49E-06mmHg at 25°C
• PKA: 16.46±0.46(Predicted)
• CAS DataBase Reference: N(8)-acetylspermidine(CAS DataBase Reference)
• NIST Chemistry Reference: N(8)-acetylspermidine(13431-24-8)
• EPA Substance Registry System: N(8)-acetylspermidine(13431-24-8)

Safety Data

• Hazardous Substances Data: 13431-24-8(Hazardous Substances Data)

Usage

Definition

ChEBI: An acetylspermidine that is 1,8-diamino-4-azaoctane in which one of the hydrogens of the amino group attached to C-8 is replaced by an acetyl group.

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

Upstream product

• 86563-01-1 N⁸-acetyl-n1-phenylmethoxycarbonylspermidine 
• 5699-41-2 N-(4-aminobutyl)acetamide 
• 86550-23-4 {3-[(E)-4-Acetylamino-butylimino]-propyl}-carbamic acid benzyl ester 
• 73453-98-2 1-(4-aminobutyl)-1,2,3,4,5,6-hexahydropyrimidine 
• 126993-30-4 N¹,N⁴-dibenzyloxycarbonyl-N⁸-tert-butoxycarbonylspermidine 
• 97628-87-0 benzyl (4-aminobutyl)(3-(((benzyloxy)carbonyl)amino)propyl)carbamate 
• 68076-38-0 N¹-benzyloxycarbonyl-N³-tert-butyloxycarbonyl-spermidine 
• 126993-31-5 {3-[(4-Acetylamino-butyl)-benzyloxycarbonyl-amino]-propyl}-carbamic acid benzyl ester 
• 85681-29-4 N-[4-(Tetrahydro-pyrimidin-1-yl)-butyl]-acetamide 

Downstream Products

• 24431-54-7 4-(acetylamino)butanal 
• 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.

CONVENIENT ROUTES TO ALKYL-SUBSTITUTED POLYAMINES

Alkyl-substituted polyamines, valuable for biological studies, can be prepared from N-phenylmethoxycarbonyl-1,4-diaminobutane (1b) and N-phenylmethoxycarbonyl-4-azidobutanamine (4a) by utilising the following reactions: (i) reduction of the phenylmethoxycarbonyl group to methyl by borane and (ii) combination of the Staudinger and aza-Wittig reactions .