Ammonium bituminosulfonate

safety instructions
Surname	Ichthammol
CAS number	8029-68-3
GHS labeling of hazardous substances Caution
H and P phrases	H: 319-412
	P: 280-273-264-305 + 351 + 338-337 + 313-501

Pure ammonium bituminosulfonate is a viscous, black liquid

Ammonium bituminosulfonate , also marketed under the trademarks Ichthammol , Ichtholan and Ichthyol , is an organic chemical compound. The substance is used in medicine as an active ingredient for the treatment of some forms of skin diseases , bruises, sprains and osteoarthritis .

synthesis

In the first step, it is produced by dry distillation of kerogen-rich oil shale , a petroleum mother rock in which anoxic conditions resulted in an enrichment of organic material - mainly from dead phytoplankton . The sulphonation and subsequent neutralization of certain fractions of the crude "shale oil" (see → Tyrolean rock oil ) with ammonia results in ammonium bituminosulphonate as sulphonate salt in an aqueous solution.

If the neutralization is carried out with sodium hydroxide, a similar product is formed, sodium bituminosulfonate.

properties

Ammonium bituminosulfonate is a multicomponent mixture, largely made up of sulfonated thiophene derivatives . In contrast to tars ( coal tar ), polycyclic aromatic hydrocarbons (PAH) are only contained in small traces. From an elemental analysis, Eugen Baumann and Carl Schotten calculated a chemical formula for the active ingredient neutralized with sodium hydroxide solution in 1883 . However, Paul Gerson Unna pointed out in 1897 that, in spite of the agreement of the elemental analysis with the formula, ammonium bituminosulfonate is a “complex body”. The content of organically bound sulfur (based on the dried substance) is above 10.5% according to the pharmacopoeia requirements (Ph. Eur.).

use

The substance is used in medicine as a medicinal substance for the treatment of some forms of skin diseases such as acne , eczema , boils , psoriasis , but also bruises, sprains and osteoarthritis . The active ingredient monographed in pharmacopoeias worldwide (including the European Pharmacopoeia Ph. Eur. And American Pharmacopoeia USP) is generally used in a so-called puff ointment with a 10, 20 or 50 percent mass fraction , which turns it into a so-called "black ointment" . The German doctor Paul Gerson Unna discovered their dermatological effects .

Differentiation from materials originating in China

Materials originating in China (pinyin: yushizhi and yushizhi ruangao), which are offered outside of China as ichthammol, ichthyol or ammonium bituminosulfonate, are not in accordance with the substance definition as e.g. B. in the European (Ph.Eur.) Or American (USP) pharmacopoeia can be found. There is also no agreement with the definition laid down for CAS # 8029-68-3 ("a complex product obtained by the sulfonation and ammoniation of the distillation product from bituminous schists"). Chinese material is obtained from vegetable oils (e.g. soybean oil) through vulcanization and sulfonation. According to the definition, the origin of ammonium bituminosulphonate (or ichthammol or ichthyol), as can also be deduced from the name, goes back to a bituminous rock (kerogen-rich oil shale). A material based on vegetable oils has a fundamentally different material composition. The bitumen smell typical of the original is completely absent from the Chinese imitation.

Trade names

There are two types of ammonium bituminosulfonate on the market: the light (monographed in D in the DAC; Leukichtol) and the dark (monographed in the European Pharmacopoeia). The light variant is obtained through mild sulphonation (and thus a lower sulphate sulfur content). It is much thinner. The light variant is of little importance in practice. The light-colored sodium bituminosulphonate is used much more frequently instead. Until 2000, a comparable substance was sold under the name ammonium sulfobitol (tumenol ammonium), which was obtained from the low-sulfur shale oils of the Messel pit .

Monopreparations: Ichtho Bad (DE), Ichtholan (DE, AT, CH), Ichthyol (DE, raw material for pharmacy prescriptions), Schwarze Salbe Lichtenstein (DE), Thiobitum ® (DE), Zugsalbe effect (DE).
Combination preparations: Aknederm ointment new (DE), Bad Schallerbacher rheumatism and gout ointment (AT), Delta-Hädensa (AT), Hädensa (AT), Inotyol (AT), Ischler haemorrhoid ointment (AT), Ischler tension and abscess ointment (AT), Lindosan (AT)

literature

E. Baumann, C. Schotten: About the ichthyol . In: Monthly books for practical dermatology , Volume II, p. 257, 1883.
Paul Gerson Unna: About Ichthyol . In: Monthly booklets for practical dermatology , Volume XXV, 1897.

Individual evidence

↑ There is not yet a harmonized classification for this substance . A labeling of Ichthammol in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), which was accessed on November 6, 2017, is reproduced from a self-classification by the distributor .

↑ Fagron: Safety data sheet ammonium bituminosulfonate, Ichthammolum , accessed on November 12, 2017.

↑ J. Koch, R. Moser, J. Demel: Analysis of the ammonium bituminosulfonate Ichthyol in the archive of the pharmacy . 1985: 318 (3): 198-206.

↑ H. Ippen, G. Grimmer: Carcinogenic hydrocarbons in therapeutic "tars" in H + G magazine for skin diseases . 1993: 68 (2): 88-92.

↑ People's Republic of China Pharmacopoeia, 2010 Edition ( Chinese Medical Encyclopedia , accessed October 16, 2015).

[1] Template: CL Inventory / not harmonized There is not yet a harmonized classification for this substance . A labeling of Ichthammol in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), which was accessed on November 6, 2017, is reproduced from a self-classification by the distributor .