N-Phenyl-1-naphthylamine

CAS No. 90-30-2

Formula: C16H13N
Basic Info

N-Phenylnaphthalen-1-amine (NPN) is a nonpolar, hydrophobic molecule with the chemical formula C 16NH 13. This molecule is most 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. 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.

Formula
C16H13N
Molecular Weight
219.281
Exact Mass
219.105
LogP
4.6564
PSA
12.03
Synonyms

1-Naphthalenamine, N-phenyl-

N-phenylnaphthalen-1-amine

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Properties
Appearance & Physical State
off-white to slight brown crystalline powder
Density
1.1
Boiling Point
335ºC
Melting Point
58-62ºC
Flash Point
190.2ºC
Water Solubility
insoluble
Stability
Stable. Incompatible with strong oxidizing agents, strong acids.
Safety Info
RTECS
QM4500000
Safety Statements
S26-S29-S37/39-S61
WGK Germany
2
Risk Statements
R22; R36/37/38; R50/53
HS Code
3812301000
RIDADR
3077
Hazard Class
9
Packing Group
III
Hazard Codes
Spectrum
NMR Spectrum 1H NMR : 400 MHz in CDCl3
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IR Spectrum IR : KBr disc
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Mass Spectrum Mass
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Analysis Methods
Van Den Dool and Kratz RI, non-polar column, custom temperature program
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Column Shape
Capillary
Active Phase(℃)
5 % Phenyl methyl siloxane
Retention index
2135.
Temperature Control
Method
custom temperature program
Comments
25. m/0.31 mm/0.52 μm, He; Program: 50C(2min) => (20C/min) => 120C => (7C/min) => 310C(10min)
Reference
Yasuhara, A.Shiraishi, H.Nishikawa, M.Yamamoto, T.Uehiro, T.Nakasugi, O.Okumura, T.Kenmotsu, K.Fukui, H.Nagase, M.Ono, Y.Kawagoshi, Y.Baba, K.Noma, Y.Determination of organic components in leachates from hazardous waste disposal sites in Japan by gas chromatography-mass spectrometryJ. Chromatogr. A1997, 774, 1-2, 321-332.
Normal alkane RI, non-polar column, custom temperature program
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Column Shape
Capillary
Active Phase(℃)
HP-5
Retention index
2135.
Temperature Control
Method
custom temperature program
Comments
30. m/0.25 mm/0.25 μm; Program: not specified
Reference
Zhao, Y.Li, J.Xu, Y.Duan, H.Fan, W.Zhao, G.EXtraction, preparation and identification of volatile compounds in Changyu XO brandyChinese J. Chromatogr.2008, 26, 2, 212-222.
Synthesis Route
Toxicity
TUMORIGENIC DATA
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Type of Test
TDLo - Lowest published toxic dose
Exposure Route
Oral
Species Observed
Rodent - mouse
Dose/Duration
5400 mg/kg/9W-I
Toxic Effects
Tumorigenic--Carcinogenic by RTECS criteria<br>Lungs, Thorax, or Respiration--tumors<br>Kidney, Ureter, Bladder--Kidney tumors
Reference
Cancer Research. (Public Ledger Building, Suit 816, 6th & Chestnut Sts., Philadelphia, PA 19106) V.1- 1941- Volume(issue)/page/year: 44,3098,1984
TUMORIGENIC DATA
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Type of Test
TD - Toxic dose (other than lowest)
Exposure Route
Oral
Species Observed
Rodent - mouse
Dose/Duration
17280 mg/kg/9W-I
Toxic Effects
Tumorigenic--Carcinogenic by RTECS criteria<br>Lungs, Thorax, or Respiration--tumors<br>Kidney, Ureter, Bladder--Kidney tumors
Reference
Cancer Research. (Public Ledger Building, Suit 816, 6th & Chestnut Sts., Philadelphia, PA 19106) V.1- 1941- Volume(issue)/page/year: 44,3098,1984
MUTATION DATA
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Type of Test
Mutation in microorganisms
Exposure Route
Species Observed
Dose/Duration
10 ug/plate
Toxic Effects
--
Reference
Shiyan Shengwu Xuebao. Journal of Experimental Biology. (China International Book Trading Corp., POB 2820, Beijing, Peop. Rep. China) V.1- 1953- Suspended 1966-77. Volume(issue)/page/year: 12,41,1979
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