DIPROPYLENETRIAMINE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C6H17N3
Molecular Weight	131.2193
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

NCCCNCCCN

InChI

InChIKey=OTBHHUPVCYLGQO-UHFFFAOYSA-N

InChI=1S/C6H17N3/c7-3-1-5-9-6-2-4-8/h9H,1-8H2

HIDE SMILES / InChI

Molecular Formula	C6H17N3
Molecular Weight	131.2193
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: http://www.chemicalbook.com/ChemicalProductProperty_EN_CB2181802.htm
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/3255245 | https://www.ncbi.nlm.nih.gov/pubmed/3140710 | https://www.ncbi.nlm.nih.gov/pubmed/23418450 | http://www.abcam.com/dpta-nonoate-dipropylenetriamine-nonoate-ab145198.html

Norspermidine (1,7-diamino-4-azaheptane or dipropylenetriamine) is a structural homologue of the natural polyamine spermidine. Norspermidine and its metal complexes exert antineoplastic properties. Dipropylenetriamine NONOate is used as a donor of nitric oxide.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Spermidine/spermine N(1)-acetyltransferase 1 1 Target ID: CHEMBL4286 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1989509	Substrate 661
cell proliferation 28 Target ID: GO:0008283 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23418450	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Cancer 609 Sources: https://www.ncbi.nlm.nih.gov/pubmed/3255245 https://www.ncbi.nlm.nih.gov/pubmed/3140710 https://www.ncbi.nlm.nih.gov/pubmed/23418450	Primary		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Spermidine is a morphogenetic determinant for cell fate specification in the male gametophyte of the water fern Marsilea vestita.	2010-11	21097708
[2-({3-[(3-Amino-prop-yl)amino]-prop-yl}imino-meth-yl)phenolato-κO,N,N'',N''']bromidocopper(II).	2010-10-30	21588891
Complete genome sequence of Sulfurimonas autotrophica type strain (OK10).	2010-10-27	21304749
Complete genome sequence of Vulcanisaeta distributa type strain (IC-017).	2010-09-28	21304741
Evolution of substrate specificity within a diverse family of beta/alpha-barrel-fold basic amino acid decarboxylases: X-ray structure determination of enzymes with specificity for L-arginine and carboxynorspermidine.	2010-08-13	20534592
Polyamine biosynthetic diversity in plants and algae.	2010-07	20227886
Bacterial lifestyle in a deep-sea hydrothermal vent chimney revealed by the genome sequence of the thermophilic bacterium Deferribacter desulfuricans SSM1.	2010-06	20189949
Variation of the ground spin state in homo- and hetero-octanuclear copper(II) and nickel(II) double-star complexes with a meso-helicate-type metallacryptand core.	2010-05-28	21491690
Evaluation method for polyamine uptake by N(1)-dansylspermine.	2010-02	19956993
Caenorhabditis elegans P5B-type ATPase CATP-5 operates in polyamine transport and is crucial for norspermidine-mediated suppression of RNA interference.	2010-01	19762559
Novel design principles enable specific targeting of imaging and therapeutic agents to necrotic domains in breast tumors.	2010	20497549
Spermidine regulates Vibrio cholerae biofilm formation via transport and signaling pathways.	2009-10	19694812
Molecular-programmed self-assembly of homo- and heterometallic tetranuclear coordination compounds: synthesis, crystal structures, and magnetic properties of rack-type Cu(II)(2)M(II)(2) complexes (M = Cu and Ni) with tetranucleating phenylenedioxamato bridging ligands.	2009-06-01	19331374
Structure-activity relationships of lipopolysaccharide sequestration in N-alkylpolyamines.	2009-05-01	19332373
Adaptations to submarine hydrothermal environments exemplified by the genome of Nautilia profundicola.	2009-02	19197347
Evaluation of anti-inflammatory and antioxidant activities of copper (II) Schiff mono-base and copper(II) Schiff base coordination compounds of dien with heterocyclic aldehydes and 2-amino-5-methyl-thiazole.	2008-12	19005947
In vitro and in vivo inhibition of plant polyamine oxidase activity by polyamine analogues.	2008-10	18783804
Absorption spectroscopic and FTIR studies on EDA complexes between TNT (2,4,6-trinitrotoluene) with amines in DMSO and determination of the vertical electron affinity of TNT.	2008-06	17765603
Pressure response of three-dimensional cyanide-bridged bimetallic magnets.	2008-04-02	18331039
Cellular polyamines of phototrophs and heterotrophs belonging to the lower eukaryotic phyla Cercozoa, Euglenozoa, Heterokonta and Metamonada.	2008-04	18497488
Thixotropic twin-dendritic organogelators.	2008	18022971
Modulation of bacterial Type III secretion system by a spermidine transporter dependent signaling pathway.	2007-12-12	18074016
Synthesis of 2,2'-Bis(3,6,9-triazanonyl)-4,4'-bithiazole and related compounds as new DNA cleavage agents.	2007-12	18057756
Formation of spermidine or norspermidine from synthetic diacetylpolyamines by acetylpolyamine oxidase in cultured cells.	2007-12	18057731
The lithium tolerance of the Arabidopsis cat2 mutant reveals a cross-talk between oxidative stress and ethylene.	2007-12	17931347
An Arabidopsis quiescin-sulfhydryl oxidase regulates cation homeostasis at the root symplast-xylem interface.	2007-07-11	17568770
Novel cationic and neutral glycocholic acid and polyamine conjugates able to inhibit transporters involved in hepatic and intestinal bile acid uptake.	2007-03-15	17276074
Inhibition of the intestinal absorption of bile acids using cationic derivatives: mechanism and repercussions.	2007-02-01	17134679
A three-dimensional ferromagnet, [Ni(dipn)]3[Cr(CN)6]2.3H2O (dipn = dipropylene triamine), based on a cubic Cr8Ni12 unit.	2006-09-04	16933919
Heterologous expression and biochemical characterization of a polyamine oxidase from Arabidopsis involved in polyamine back conversion.	2006-08	16778015
Novel rhenium chelate system derived from dimercaptosuccinic acid for the selective labeling of biomolecules.	2005-12-26	16363864
Molecular recognition. 1. Crystal structures of hexaazamacrocyclic amines containing p-xylylene spacers and their adducts with acids.	2005-12-09	16551374
Cloning and characterization of spermidine synthase and its implication in polyamine biosynthesis in Helicobacter pylori strain 26695.	2005-10	16009566
Mechanism and structure-activity relationships of norspermidine-based peptidic inhibitors of trypanothione reductase.	2005-07-15	15922604
Substrate specificity of the bovine serum amine oxidase and in situ characterisation of aminoaldehydes by NMR spectroscopy.	2005-06-01	15863005
The unexpected formation of biologically active Cu(II) Schiff mono-base complexes with 2-thiophene-carboxaldehyde and dipropylenetriamine: crystal and molecular structure of CudptaSCl2.	2005-02	15621279
Nitric oxide covalently labels a 6-hydroxydopa-derived free radical intermediate in the catalytic cycle of copper/quinone-containing amine oxidase from lentil seedlings.	2005-01	15843144
Polyamine analysis for chemotaxonomy of thermophilic eubacteria: Polyamine distribution profiles within the orders Aquificales, Thermotogales, Thermodesulfobacteriales, Thermales, Thermoanaerobacteriales, Clostridiales and Bacillales.	2004-10	15747232
Distribution of norspermidine as a cellular polyamine within micro green algae including non-photosynthetic achlorophyllous Polytoma, Polytomella, Prototheca and Helicosporidium.	2004-10	15747227
Coordination mode of adenosine 5'-diphosphate in ternary systems containing Cu(II), Cd(II) or Hg(II) ions and polyamines.	2004-08	15271508
Membrane binding and transport of N-aminoethyl-1,2-diamino ethane (dien) and N-aminopropyl-1,3-diamino propane (propen) by rat liver mitochondria and their effects on membrane permeability transition.	2004-06-19	15204440
Bisguanidine, bis(2-aminoimidazoline), and polyamine derivatives as potent and selective chemotherapeutic agents against Trypanosoma brucei rhodesiense. Synthesis and in vitro evaluation.	2004-04-22	15084128
Preparation of gemini-type amphiphiles bearing cyclitol head groups and their application as high-performance modifiers for lipases.	2004-02-25	15013386
Polyamines of primitive apterygotan insects: springtails, silverfish and a bristletail.	2004-01	14698912
Xylylated dimers of putrescine and polyamines: influence of the polyamine backbone on spermidine transport inhibition.	2003-10-06	12951106
Cellular polyamines of the acidophilic, thermophilic and thermoacidophilic archaebacteria, Acidilobus, Ferroplasma, Pyrobaculum, Pyrococcus, Staphylothermus, Thermococcus, Thermodiscus and Vulcanisaeta.	2003-10	14673752
Oxamato-bridged trinuclear NiIICuIINiII complexes: a new (NiIICuIINiII)2 hexanuclear complex and supramolecular structures. Characterization and magnetic properties.	2003-05-19	12739979
Recent news related to substrates and inhibitors of plant amine oxidases.	2003-04-11	12686157
Two aerosolized nitric oxide adducts as selective pulmonary vasodilators for acute pulmonary hypertension.	2003-03	12628890
Effects of exogenous polyamines on growth, toxicity, and toxin profile of dinoflagellate Alexandrium minutum.	2003-02	12749197

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

High-dose norspermidine (1,7-diamino-4-azaheptane or dipropylenetriamine) had bactericide effect on P. aeruginosa, and norspermidine began to inhibit biofilm formation and eradicate 24-h mature biofilm at concentration of 0.1 and 1 mmol/L, respectively, probably by preventing cell-surface attachment, inhibiting swimming motility, and downregulating QS-related genes expression.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 21:01:26 GMT 2025` Edited by `admin` on `Mon Mar 31 21:01:26 GMT 2025`
Record UNII	RN1144MGND
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NSC-7773

Preferred Name

English

DIPROPYLENETRIAMINE

Official Name

English

N-(3-AMINOPROPYL)-1,3-PROPANEDIAMINE

Systematic Name

English

3,3'-IMINOBISPROPYLAMINE

Common Name

English

4-AZAHEPTAMETHYLENEDIAMINE

Common Name

English

DI(3-AMINOPROPYL)AMINE

Systematic Name

English

1,7-DIAMINO-4-AZAHEPTANE

Systematic Name

English

3,3'-IMINODIPROPYLAMINE

Common Name

English

1,3-PROPANEDIAMINE, N-(3-AMINOPROPYL)-

Systematic Name

English

CALDINE

Common Name

English

1,5,9-TRIAZANONANE

Systematic Name

English

DIPROPYLAMINE, 3,3'-DIAMINO-

Common Name

English

BIS(3-AMINOPROPYL)AMINE

Systematic Name

English

1,3-PROPANEDIAMINE,N-(3-AMINOPROPYL)-

Systematic Name

English

4-AZAHEPTANE-1,7-DIAMINE

Systematic Name

English

1,3-PROPANEDIAMINE, N1-(3-AMINOPROPYL)-

Systematic Name

English

3,3'-IMINODI(PROPYLAMINE)

Systematic Name

English

3,3'-IMINOBIS(PROPYLAMINE)

Systematic Name

English

Code System Code Type Description

WIKIPEDIA

Norspermidine