:N-Phenylnaphthalen-1-amine

{{technical|date=November 2011}}

{{DISPLAYTITLE:N-Phenylnaphthalen-1-amine}}

{{Chembox

| Name=N-Phenylnaphthalen-1-amine

| ImageFile = N-Phenylnaphthalen-1-amine.svg

| ImageSize = 200px

| PIN = N-Phenylnaphthalen-1-amine

| OtherNames = {{ubl|Anilinonaphthalene|α-Naphthylphenylamine}}

|Section1={{Chembox Identifiers

| Abbreviations = PANa

| CASNo = 90-30-2

| CASNo_Ref = {{cascite|correct|}}

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

| UNII = 5I112077IN

| PubChem = 7013

| ChemSpiderID = 6746

| SMILES = c3c(Nc1ccccc1)c2ccccc2cc3

| InChI = 1/C16H13N/c1-2-9-14(10-3-1)17-16-12-6-8-13-7-4-5-11-15(13)16/h1-12,17H

| InChIKey = XQVWYOYUZDUNRW-UHFFFAOYAN

| StdInChI = 1S/C16H13N/c1-2-9-14(10-3-1)17-16-12-6-8-13-7-4-5-11-15(13)16/h1-12,17H

| StdInChIKey = XQVWYOYUZDUNRW-UHFFFAOYSA-N

}}

|Section2={{Chembox Properties

| C=16 | H=13 | N=1

| Appearance =

| Density =

| MeltingPt =

| BoilingPt =

| Solubility =

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|Section3={{Chembox Hazards

| MainHazards =

| FlashPt =

| AutoignitionPt =

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N-Phenylnaphthalen-1-amine (NPN) is an aromatic amine with the chemical formula {{chem|C|16|H|12|NH}}.

This molecule is notable for its binding affinity in mouse major urinary protein (MUP). This ligand has the greatest binding affinity of all MUP binding ligand discovered, including 2-sec-butyl-4,5-dihydrothiazole (SBT), 6-hydroxy-6-methyl-3-heptanone (HMH), and 3-isobutyl-2-methoxypyrazine (IBMP). NPN binds 28 times tighter than SBT. It also makes 38 nonpolar contacts to MUP, whereas IBMP only makes 15 contacts which are the next most nonpolar contacts.{{cite journal|vauthors = Pertinhez TA, Ferrari E, Casali E, Patel JA, Spisni A, Smith LJ |title=The binding cavity of mouse major urinary protein is optimised for a variety of ligand binding modes|journal=Biochemical and Biophysical Research Communications|date=1 December 2009|volume=390|issue=4|pages=1266–1271|doi=10.1016/j.bbrc.2009.10.133|pmid=19878650}} There is a slight difference in the binding affinities and forms for NPN bound in wild-type MUP and the Y120F MUP mutant. In wild-type MUP there is just enough room for the amine group of NPN to makes a water mediated hydrogen bond to Tyr120, whereas in Y120F MUP mutant, there is a slight shift and the amine group makes a direct hydrogen bond to Tyr120. Much is still unknown about the entropic and enthalpic effects of the MUP binding site.{{cite journal|last=Homans|first=SW|title=Water, water everywhere--except where it matters?|journal=Drug Discovery Today|date=July 2007|volume=12|issue=13–14|pages=534–9|pmid=17631247|url=http://www.mendeley.com/research/water-water-everywhereexcept-it-matters-1/|doi=10.1016/j.drudis.2007.05.004|url-access=subscription}}