:Norspermidine

{{chembox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 366825299

| ImageFile = Bis(3-aminopropyl)amin Struktur.svg

| ImageFile_Ref = {{chemboximage|correct|??}}

| ImageSize = 250

| ImageName = Skeletal formula of norspermidine

| ImageFile1 = Norspermidine molecule ball.png

| ImageSize1 = 220

| ImageAlt1 = Ball-and-stick model of the norspermidine molecule

| PIN = N¹-(3-Aminopropyl)propane-1,3-diamine

|Section1={{Chembox Identifiers

| CASNo = 56-18-8

| CASNo_Ref = {{cascite|correct|CAS}}

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = RN1144MGND

| PubChem = 5942

| ChemSpiderID = 5729

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| EINECS = 200-261-2

| UNNumber = 2269

| KEGG = C03375

| KEGG_Ref = {{keggcite|changed|kegg}}

| MeSHName = norspermidine

| ChEBI = 16841

| ChEBI_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 28743

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| RTECS = JL9450000

| Beilstein = 1071254

| Gmelin = 26839

| 3DMet = B00581

| SMILES = NCCCNCCCN

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

| StdInChI_Ref = {{chemspidercite|correct|chemspider}}

| StdInChIKey = OTBHHUPVCYLGQO-UHFFFAOYSA-N

| StdInChIKey_Ref = {{chemspidercite|correct|chemspider}}

}}

|Section2={{Chembox Properties

| C=6 | N=3 | H=17

| Appearance = Colorless liquid

| Odor = Ichtyal, ammoniacal

| Density = 938 mg mL⁻¹

| MeltingPtK = 257 to 273

| BoilingPtK = 513.75

| LogP = −0.826

| RefractIndex = 1.481–1.482

}}

|Section3={{Chembox Hazards

| ExternalSDS = [https://fscimage.fishersci.com/msds/30009.htm fishersci.com]

| GHSPictograms = {{gHS corrosion}} {{gHS skull and crossbones}}

| GHSSignalWord = DANGER

| HPhrases = {{h-phrases|302|311|314|317|330}}

| PPhrases = {{p-phrases|260|280|284|305+351+338|310}}

| FlashPtC = 117

| AutoignitionPtC = 280

| LD50 = 738 mg kg⁻¹ (oral, rat)

}}

|Section4={{Chembox Related

| OtherFunction_label = amines

| OtherFunction = {{unbulleted list|Dipropylamine|Methyl-n-amylnitrosamine|Spermidine}}

| OtherCompounds = Agmatine

}}

}}

Norspermidine is a polyamine of similar structure to the more common spermidine. While norspermidine has been found to occur naturally in some species of plants,{{cite journal | author = Rodriguez-Garay, B| title = Detection of Norspermidine and Norspermine in Medicago sativa L. (Alfalfa) | journal = Plant Physiology | volume = 89 | issue = 2| pages = 525–529 | year = 1989 | issn = 0032-0889 | doi = 10.1104/pp.89.2.525 | pmid = 16666576 | pmc = 1055875 |display-authors=etal}}{{cite journal | author = Hamana, K| title = Unusual polyamines in aquatic plants: the occurrence of homospermidine, norspermidine, thermospermine, norspermine, aminopropylhomospermidine, bis(aminopropyl)ethanediamine, and methylspermidine | journal = Can. J. Bot. | volume = 76 | issue = 1 | pages = 130–133 | year = 1998 | doi = 10.1139/cjb-76-1-130 |display-authors=etal}} bacteria,{{cite journal | author = Yamamoto, S| title = Occurrence of norspermidine in some species of genera Vibrio and Beneckea | journal = Biochem Biophys Res Commun | volume = 87 | issue = 4 | pages = 1102–1108 | date = Apr 27, 1979 | pmid = 313792 | doi = 10.1016/S0006-291X(79)80021-2 |display-authors=etal}} and algae,{{cite journal |author1=Hamana, K |author2=Matsuzaki, S | title = Widespread Occurrence of Norspermidine and Norspermine in Eukaryotic Algae | journal = J. Biochem. | volume = 91 | issue = 4 | pages = 1321–1328 | year = 1982 |doi=10.1093/oxfordjournals.jbchem.a133818 | issn = 0021-924X | pmid = 7096289 }} it is not known to exist in humans.

Norspermidine is being researched for use as a cancer medication.{{cite journal | author = Prakash, NJ| title = Antitumor activity of norspermidine, a structural homologue of the natural polyamine spermidine | journal = Anticancer Res. | volume = 8 | issue = 4 | pages = 563–568 | year = 1988 | pmid = 3140710 |display-authors=etal}}{{cite book | author = Sunkara, PS| title = Progress in Polyamine Research | chapter = Mechanism of antitumor activity of norspermidine, a structural homologue of spermidine | series = Adv Exp Med Biol | volume = 250 | pages = 707–716 | year = 1988 | pmid = 3255245 | doi=10.1007/978-1-4684-5637-0_62| isbn = 978-1-4684-5639-4 |display-authors=etal}}