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Drying acetanilide

Acetanilide^[5] is an odourless solid chemical of leaf or flake-like appearance. It is also known as N-phenylacetamide, acetanil, or acetanilid, and was formerly known by the trade name Antifebrin.

Preparation and properties

Acetanilide can be produced by reacting acetic anhydride with aniline:

C₆H₅NH₂ + (CH₃CO)₂O → C₆H₅NHCOCH₃ + CH₃COOH

The preparation used to be a traditional experiment in introductory organic chemistry lab classes,^[6] but it has now been widely replaced by the preparation of either paracetamol or aspirin, both of which teach the same practical techniques (especially recrystallization of the product) but which avoid the use of aniline, a suspected carcinogen.

Acetanilide is slightly soluble in water, and stable under most conditions.^[4] Pure crystals are plate shaped and colorless to white.

Applications

Acetanilide is used as an inhibitor of hydrogen peroxide decomposition and is used to stabilize cellulose ester varnishes. It has also found uses in the intermediation in rubber accelerator synthesis, dyes and dye intermediate synthesis, and camphor synthesis. Acetanilide is used for the production of 4-acetamidobenzenesulfonyl chloride, a key intermediate for the manufacture of the sulfa drugs.^[7] It is also a precursor in the synthesis of penicillin and other pharmaceuticals.^[2]

In the 19th century acetanilide was one of a large number of compounds used as experimental photographic developers.

Pharmaceutical use

Acetanilide was the first aniline derivative serendipitously found to possess analgesic as well as antipyretic properties, and was quickly introduced into medical practice under the name of Antifebrin by A. Cahn and P. Hepp in 1886.^[8] But its (apparent) unacceptable toxic effects, the most alarming being cyanosis due to methemoglobinemia, prompted the search for supposedly less toxic aniline derivatives such as phenacetin.^[9] After several conflicting results over the ensuing fifty years, it was established in 1948 that acetanilide was mostly metabolized to paracetamol (USAN: acetaminophen) in the human body, and that it was the paracetamol that was responsible for the analgesic and antipyretic properties.^[10]^[11]^[12]^[13] The observed methemoglobinemia after acetanilide administration was ascribed to the small proportion of acetanilide that is hydrolyzed to aniline in the body.^{[note 1]} Acetanilide is no longer used as a drug in its own right, although the success of its metabolite – paracetamol (acetaminophen) – is well known.

Notes

^ The presence of aniline as an impurity in 19th century batches of acetanilide drugs cannot be ruled out. In this sense as well, paracetamol (acetaminophen) is safer than acetanilide, as (1) the corresponding impurity would be 4-aminophenol, which is less toxic than aniline; and (2) in vivo hydrolysis of the amide group in paracetamol appears to be negligible.

References

^ Weast, Robert C., ed. (1981). CRC Handbook of Chemistry and Physics (62nd ed.). Boca Raton, FL: CRC Press. p. C-67. ISBN 0-8493-0462-8. .
^ ^a ^b Acetanilide (PDF), SIDS Initial Assessment Report, Geneva: United Nations Environment Programme, September 2003 .
^ HSNO Chemical Classification Information Database, New Zealand Environmental Risk Management Authority, retrieved 2009-08-26 .
^ ^a ^b Safety data for acetanilide, Physical Chemistry Laboratory, University of Oxford .
^ Acetanilide .
^ See, e.g., The preparation of acetanilide from aniline, Department of Chemistry, University of the West Indies at Mona, Jamaica, retrieved 2009-08-26 ; Reeve, Wilkins; Lowe, Valerie C. (1979), "Preparation of Acetanilide from Nitrobenzene", J. Chem. Educ. 56 (7): 488, doi:10.1021/ed056p488 : the latter preparation includes the reduction of nitrobenzene to aniline.
^ Ashford's Dictionary of Industrial Chemicals (PDF) (Third ed.). 2011. p. 33.
^ Cahn, A.; Hepp, P. (1886), "Das Antifebrin, ein neues Fiebermittel", Centralbl. Klin. Med. 7: 561–64 .
^ Bertolini, A.; Ferrari, A.; Ottani, A.; Guerzoni, S.; Tacchi, R.; Leone, S. (2006), "Paracetamol: new vistas of an old drug", CNS Drug Reviews 12 (3–4): 250–75, doi:10.1111/j.1527-3458.2006.00250.x, PMID 17227290 .
^ Lester, D.; Greenberg, L. A. (1947), "Metabolic fate of acetanilide and other aniline derivatives. II. Major metabolites of acetanilide in the blood", J. Pharmacol. Exp. Ther. 90 (1): 68, PMID 20241897 .
^ Brodie, B. B.; Axelrod, J. (1948), "The estimation of acetanilide and its metabolic products, aniline, N-acetyl p-aminophenol and p-aminophenol (free and total conjugated) in biological fluids and tissues", J. Pharmacol. Exp. Ther. 94 (1): 22–28, PMID 18885610 .
^ Brodie, B. B.; Axelrod, J. (1948), "The fate of acetanilide in man" (PDF), J. Pharmacol. Exp. Ther. 94 (1): 29–38, PMID 18885611
^ Flinn, Frederick B.; Brodie, Bernard B. (1948), "The effect on the pain threshold of N-acetyl p-aminophenol, a product derived in the body from acetanilide", J. Pharmacol. Exp. Ther. 94 (1): 76–77, PMID 18885618 .

English Journal

Protective effects of the pyrolyzates derived from bamboo against neuronal damage and hematoaggregation.

Hong EJ1, Jung EM, Lee GS, Kim JY, Na KJ, Park MJ, Kang HY, Choi KC, Seong YH, Choi IG, Jeung EB.
Journal of ethnopharmacology.J Ethnopharmacol.2010 Apr 21;128(3):594-9. doi: 10.1016/j.jep.2010.01.045. Epub 2010 Feb 1.
ETHNOPHARMACOLOGICAL RELEVANCE: Bamboo species are thought to be originally from Central China, but are now found in many temperate and semi-tropical regions around the world. Although the extracts from bamboo may have antioxidant activities and anti-inflammatory effects, their exact biological acti
PMID 20117201

[CONTRIBUTION TO THE LIVER FUNCTION TESTS BY ANTIFEBRIN LOADING].

MATTHEY M.
Schweizerische medizinische Wochenschrift.Schweiz Med Wochenschr.1964 Jan 11;94:41-6.
PMID 14133470

An Inquiry Regarding the Importance of Ill-Effects Following the Use of Antipyrin, Antifebrin, & Phenacetin Conducted by the Therapeutic Committee of the British Medical Association.

Leech DJ, Hunter W.
British medical journal.Br Med J.1894 Jan 13;1(1724):85-90.
PMID 20754618

Japanese Journal

不感蒸泄竝ニ呼吸瓦斯代謝ニ關スル實驗的研究（第4報）解熱劑竝ニ催眠劑ノ影響ニ就テ

永山太郎
岡山医学会雑誌 44(10), 2630-2644, 1932-10-31
… Er wurde am deutlichsten durch Antifebrin, Chloralhydrat und Luminal herabgesetzt, und nahm bei Antipyrin und Natrium salicylicum nur wenig ab. … 3) Antifebrin, Morphin, Veronal und Luminal sind im stande, das Therminfieber zu unterdrücken, dagegen Antipyrin, Pyramidon, Chinin, Natr. …
NAID 120003056082

諸種藥物ノ炎症抑制作用ニ就テ

森田權平
日本藥物學雜誌 3(2), 233-244,en12, 1926
… genügend loslich, per os.<BR>Resultate Antipyrin, Antifebrin, Neopyrin, salizylsaures Natrium, Atophan, Atophanyl, salzsaures Salz von Chinin, Cinchonin, Chinidin, Cinchonidin und Sinomenin, Colchicin, Morphin-hydrochlorid, Chloralhydrat, Chlorcalcium oder salzsäure wirken mehr oder weniger deutlich entzündungshemmend. …
NAID 130003727419

「アンチフェブリン」 (Antifebrin) ノ窒扶斯ニ於ケル効用

グリュー子ベルグ
順天堂医学 M20(3), 3_20_1-3_22, 1887
NAID 130005079337

Related Pictures

Some of the significant changes in the IR Drying acetanilide This is the chemical structure of ANTIFEBRIN of the early pain reliever Antifebrin 1900 calendar february Mass spectrum (electron ionization)

★リンクテーブル★

リンク元

「アセトアニリド」

Acetanilide
Names
	IUPAC names N-phenylacetamide; N-phenylethanamide
Identifiers
CAS Number	103-84-4
ChEBI	CHEBI:28884
ChEMBL	ChEMBL269644
ChemSpider	880
EC Number	203-150-7
Jmol interactive 3D	Image
KEGG	C07565
UNII	SP86R356CC
	InChI InChI=1S/C8H9NO/c1-7(10)9-8-5-3-2-4-6-8/h2-6H,1H3,(H,9,10) Key: FZERHIULMFGESH-UHFFFAOYSA-N ; InChI=1/C8H9NO/c1-7(10)9-8-5-3-2-4-6-8/h2-6H,1H3,(H,9,10) Key: FZERHIULMFGESH-UHFFFAOYAA ;
	SMILES O=C(Nc1ccccc1)C ;
Properties
Chemical formula	C8H9NO
Molar mass	135.17 g·mol−1
Odor	Odorless
Density	1.219 g/cm3
Melting point	114.3 °C (237.7 °F; 387.4 K)
Boiling point	304 °C (579 °F; 577 K)
Solubility in water	<0.56 g/100 mL (25 °C)
Solubility	Soluble in ethanol, diethyl ether, acetone, benzene
log P	1.16 (23 °C)
Vapor pressure	2 Pa (20 °C)
Dipole moment	2.71
Hazards
Safety data sheet	External MSDS
GHS pictograms
GHS signal word	WARNING
GHS hazard statements	H302
GHS precautionary statements	P264, P270, P301+312, P330, P501
Flash point	174 °C (345 °F; 447 K)
Autoignition; temperature	545 °C (1,013 °F; 818 K)
	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: acetanilide
同: アンチフェブリン antifebrin

[14] The presence of aniline as an impurity in 19th century batches of acetanilide drugs cannot be ruled out. In this sense as well, paracetamol (acetaminophen) is safer than acetanilide, as (1) the corresponding impurity would be 4-aminophenol, which is less toxic than aniline; and (2) in vivo hydrolysis of the amide group in paracetamol appears to be negligible.

[1] Weast, Robert C., ed. (1981). CRC Handbook of Chemistry and Physics (62nd ed.). Boca Raton, FL: CRC Press. p. C-67. ISBN 0-8493-0462-8. .

[SIDS-2] Acetanilide (PDF), SIDS Initial Assessment Report, Geneva: United Nations Environment Programme, September 2003 .

[3] HSNO Chemical Classification Information Database, New Zealand Environmental Risk Management Authority, retrieved 2009-08-26 .

[MSDS-4] Safety data for acetanilide, Physical Chemistry Laboratory, University of Oxford .

[5] Acetanilide .

[6] See, e.g., The preparation of acetanilide from aniline, Department of Chemistry, University of the West Indies at Mona, Jamaica, retrieved 2009-08-26 ; Reeve, Wilkins; Lowe, Valerie C. (1979), "Preparation of Acetanilide from Nitrobenzene", J. Chem. Educ. 56 (7): 488, doi:10.1021/ed056p488 : the latter preparation includes the reduction of nitrobenzene to aniline.

[7] Ashford's Dictionary of Industrial Chemicals (PDF) (Third ed.). 2011. p. 33.

[8] Cahn, A.; Hepp, P. (1886), "Das Antifebrin, ein neues Fiebermittel", Centralbl. Klin. Med. 7: 561–64 .

[pmid17227290-9] Bertolini, A.; Ferrari, A.; Ottani, A.; Guerzoni, S.; Tacchi, R.; Leone, S. (2006), "Paracetamol: new vistas of an old drug", CNS Drug Reviews 12 (3–4): 250–75, doi:10.1111/j.1527-3458.2006.00250.x, PMID 17227290 .

[10] Lester, D.; Greenberg, L. A. (1947), "Metabolic fate of acetanilide and other aniline derivatives. II. Major metabolites of acetanilide in the blood", J. Pharmacol. Exp. Ther. 90 (1): 68, PMID 20241897 .

[11] Brodie, B. B.; Axelrod, J. (1948), "The estimation of acetanilide and its metabolic products, aniline, N-acetyl p-aminophenol and p-aminophenol (free and total conjugated) in biological fluids and tissues", J. Pharmacol. Exp. Ther. 94 (1): 22–28, PMID 18885610 .

[12] Brodie, B. B.; Axelrod, J. (1948), "The fate of acetanilide in man" (PDF), J. Pharmacol. Exp. Ther. 94 (1): 29–38, PMID 18885611

[13] Flinn, Frederick B.; Brodie, Bernard B. (1948), "The effect on the pain threshold of N-acetyl p-aminophenol, a product derived in the body from acetanilide", J. Pharmacol. Exp. Ther. 94 (1): 76–77, PMID 18885618 .

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antifebrin