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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/09/08 11:40:15」(JST)

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2-Naphthylamine is an aromatic amine. It is used to make azo dyes. It is a known human carcinogen and has largely been replaced by less toxic compounds. 2-Naphthylamine is prepared by heating 2-naphthol with ammonium zinc chloride to 200-210 °C; or in the form of its acetyl derivative by heating 2-naphthol with ammonium acetate to 270-280 °C. It forms odorless, colorless plates which melt at 111-112 °C. It gives no color with ferric chloride. When reduced by sodium in boiling amyl alcohol solution it forms alicyclic tetrahydro-3-naphthylamine, which has most of the properties of the aliphatic amines; it is strongly alkaline in reaction, has an ammoniacal odor and cannot be diazotized. On oxidation it yields ortho-carboxy-hydrocinnamic acid, HO₂CC₆H₄CH₂CH₂CO₂H. Numerous sulfonic acids derived from 2-naphthylamine are known. Of these, the δ-acid and Bronner's acid are of more value technically, since they combine with ortho-tetrazoditolyl to produce fine red dye-stuffs.

Role in disease

2-Naphthylamine is found in cigarette smoke and suspected to contribute to the development of bladder cancer.^[2]

It is activated in the liver but quickly deactivated by conjugation to glucuronic acid. In the bladder, glucuronidase re-activates it by deconjugation, which leads to the development of bladder cancer.

References

^ ^a ^b ^c ^d ^e "NIOSH Pocket Guide to Chemical Hazards #0442". National Institute for Occupational Safety and Health (NIOSH).
^ CDC - NIOSH Pocket Guide to Chemical Hazards

UpToDate Contents

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1. Epidemiology and risk factors of urothelial (transitional cell) carcinoma of the bladder
2. 抗原虫治療 antiprotozoal therapies
3. 膀胱癌のスクリーニング screening for bladder cancer
4. アフリカ・トリパノソーマ症の臨床症状、診断、および治療 clinical manifestations diagnosis and treatment of african trypanosomiasis

English Journal

Probing conformational changes in lipoxygenases upon membrane binding: Fine-tuning by the active site inhibitor ETYA.

Di Venere A, Nicolai E, Ivanov I, Dainese E, Adel S, Angelucci BC, Kuhn H, Maccarrone M, Mei G.SourceDepartment of Experimental Medicine and Surgery, Tor Vergata University of Rome, Via Montpellier 1, 00133 Rome, Italy.
Biochimica et biophysica acta.Biochim Biophys Acta.2014 Jan;1841(1):1-10. doi: 10.1016/j.bbalip.2013.08.015. Epub 2013 Sep 3.
Lipoxygenases (LOXs) are lipid-peroxidizing enzymes that are involved in the metabolism of polyunsaturated fatty acids. Their biological activity includes a membrane binding process whose molecular details are not completely understood. The mechanism of enzyme-membrane interactions is thought to inv
PMID 24012824

Application of an ampholine-functionalized hybrid organic-inorganic silica material for the SPE of aromatic amines.

Chen Y, Wang T, Ma J, Liang Z, Chen M, Fang J, Gao H, Zhang L, Zhang Y.SourceXiangshan Entry-Exit Inspection and Quarantine, Xiangshan, China.
Journal of separation science.J Sep Sci.2013 Oct 31. doi: 10.1002/jssc.201300964. [Epub ahead of print]
An SPE cartridge based on an ampholine-functionalized hybrid organic-inorganic silica sorbent has been adopted for the analysis of aromatic amines including 4-aminobiphenyl, benzidine, 2-naphthylamine, p-chloroaniline, 2,4,5-trimethylaniline, and 3,3'-dichlorobenzidine. Crucial variables governing t
PMID 24178632

Electrochemical detection of the amino-substituted naphthalene compounds based on intercalative interaction with hairpin DNA by electrochemical impedance spectroscopy.

Liang G, Li T, Li X, Liu X.SourceState Key Laboratory of Water Environment Simulation, School of Environment, Beijing Normal University, Beijing 100875, PR China.
Biosensors & bioelectronics.Biosens Bioelectron.2013 Oct 15;48:238-43. doi: 10.1016/j.bios.2013.04.008. Epub 2013 Apr 15.
The amino-substituted naphthalene compounds, such as 1,8-diaminonaphthalene (1,8-DANAP), 2,3-diaminonaphthalene (2,3-DANAP), 1,5-diaminonaphthalene (1,5-DANAP), 1-naphthylamine (1-NAP) and 2-naphthylamine (2-NAP), were investigated by electrochemical impedance spectroscopy (EIS), which was based on
PMID 23693094

Japanese Journal

A New Approach to the Study of the Mechanism of Oily Soil Removal by Means of Liquid Chromatography with a Filament Yarn Column

TAGAYA Hisako,YOSHIDA Ayumi,HIGASHITSUJI Ken
Journal of oleo science 51(12), 789-798, 2002-12-01
… We measured the retention volume of 1-phenylazo-2-naphthylamine (SY5) and l-phenylazo-2-naphthylphenol (SY14) as two kinds of oily soil model on either polyester or cellulosic filaments (the stationary phase) as a function of sodium dodecyl sulfate (SDS) concentration in the mobile phase. …
NAID 10010446025

Oxidative DNA Damage Induced by a Metabolite of 2-Naphthylamine, a Smoking-related Bladder Carcinogen

OHNISHI Shiho,MURATA Mariko,KAWANISHI Shosuke
Japanese journal of cancer research : gann 93(7), 736-743, 2002-07-31
NAID 50000584131

Related Pictures

Chemicals in cigarettes Stock Photos, Images, & Pictures | Shutterstock Alfa Aesar (R)-(+)-1,1'-Bi(2-naphthylamine), 97% 250mg:Chemicals Naphthyl Illustrations and Clip Art. 8 Naphthyl royalty free illustrations and 2 - Naphthylamine (CAS 91-59-8) 2-Naphthylamine; 2-Aminonaphthalene; beta-Naphthylamine 301 Moved Permanently N-(Î³-L-Glutamyl)-4-methoxy-2-naphthylamine | Polysciences, Inc.

★リンクテーブル★

リンク元	「腎盂尿管癌」「2-ナフチルアミン」

「腎盂尿管癌」

2-Naphthylamine
Names
	IUPAC name 2-Aminonaphthalene
	Other names 2-Naphthylamine; β-Naphthylamine
Identifiers
CAS Registry Number	91-59-8
ChEBI	CHEBI:27878
ChEMBL	ChEMBL278164
ChemSpider	6790
	InChI InChI=1S/C10H9N/c11-10-6-5-8-3-1-2-4-9(8)7-10/h1-7H,11H2 ; Key: JBIJLHTVPXGSAM-UHFFFAOYSA-N ; InChI=1/C10H9N/c11-10-6-5-8-3-1-2-4-9(8)7-10/h1-7H,11H2; Key: JBIJLHTVPXGSAM-UHFFFAOYAA ;
Jmol-3D images	Image
KEGG	C02227
	SMILES c12ccccc1ccc(N)c2 ;
Properties
Chemical formula	C10H9N
Molar mass	143.19 g·mol−1
Appearance	White to red crystals
Odor	odorless
Density	1.061 g/cm3
Melting point	111 to 113 °C (232 to 235 °F; 384 to 386 K)
Boiling point	306 °C (583 °F; 579 K)
Solubility in water	miscible in hot water
Vapor pressure	1 mmHg (107° C)
Acidity (pKa)	3.92
Hazards
Flash point	157 °C; 315 °F; 430 K
Related compounds
Related compounds	2-Naphthol
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	verify (what is: /?)
	Infobox references

　　[★]

英: 腎盂癌 renal pelvic cancer; 尿管癌 ureter cancer, ureteric cancer
関: 腎尿路の腫瘍

疫学

50-70歳に多
男女比は2-4:1と男性に多い
腎盂腫瘍は腎腫瘍の約10%を占める
尿路上皮癌の4-5%

病因

タバコ、コーヒー、人工甘味料
化学発癌物質

芳香族アミン

2-naphthylamine

benzidine

薬剤

鎮痛剤(フェナセチン、アセトアミノフェン)
抗癌剤(シクロホスファミド)
造影剤(トロトラスト)

疾患

バルカン腎症

病理

1. 移行上皮癌が大部分

移行上皮癌(90%)、扁平上皮癌(3-10%)、腺癌や未分化癌(1%以下)

2. 多中心性で膀胱にも発生する (2割程度の症例で膀胱に併発)

症状

無症候性血尿
側腹部痛(血塊や腫瘍組織による尿路閉塞のため)
側腹部腫瘤形成

診断

1. 静脈性尿路造影(IVP,DIP)、逆行性腎盂造影、経皮的腎盂尿管造影

陰影欠損像や尿路閉塞所見

2. CT、MRI

腫瘍像、リンパ節転移、多臓器への転移の有無

3. 内視鏡

膀胱腫瘍と腎盂尿管腫瘍の確認

4. 尿細胞診

：陽性率は40-60%なので、腫瘍を疑った場合しつこくやる

(血管造影)

新生血管に乏しい

治療法

1. 根治的手術療法：腎尿管全摘除兼膀胱部分切除術
2. 保存的手術療法：開放手術、内視鏡手術

再発するので、結局1.をやらざるを得ないことが多いらしい

3. 非手術療法：多剤併用化学療法(M-VAC)、放射線療法
4. BCGの腎盂内注入療法：上部尿路のcarcinoma in situ(CIS)に対する治療

2/3の症例で癌が消えるらしい。

予後

表在性腫瘍は予後良好で、浸潤性腫瘍は予後不良
扁平上皮癌は予後不良
異型度、浸潤度どちらも5年生存率に影響する。
尿管は筋層が薄く、浸潤しやすいので、尿管癌が見つかった場合、浸潤度はT2以降である。

「2-ナフチルアミン」

　　[★]

英: 2-naphthylamine
同: β-ナフチルアミン β-naphthylamine、2-アミノナフタレン 2-aminonaphthalene、2-ナフタリジン 2-naphthalidine、2-ナフチラミン
関: 労働基準法施行規則

[show details]

β-ナフチルアミン : 約 5,920 件
2-ナフチルアミン : 約 7,230 件
βナフチルアミン : 約 5,920 件
2ナフチルアミン : 約 7,230 件

[PGCH-1] "NIOSH Pocket Guide to Chemical Hazards #0442". National Institute for Occupational Safety and Health (NIOSH).

[2] CDC - NIOSH Pocket Guide to Chemical Hazards

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