arsphenamine

Also known as Salvarsan, arsenphenolamine hydrochloride, 4,4'-arsenobis(2-aminophenol) dihydrochloride, 3,3'-diamino-4,4'-dihydroxyarsenobenzene dihydrochloride, Ehrlich 606, 4,4'-(diarsene-1,2-diyl)bis(2-aminophenol) dihydrochloride, 4,4'-(1,2-diarsenediyl)bis(2-aminophenol) dihydrochloride

thumb|right|300px|The structure of arsphenamine has been proposed to be akin to azobenzene (A). Salvarsan is now assumed to be a mixture of the trimer (B) and the pentamer (C).

Chemical data

Formula: C12H14As2Cl2N2O2
Molecular weight: 439 g/mol
IUPAC name: [5-(3-azaniumyl-4-hydroxyphenyl)arsanylidenearsanyl-2-hydroxyphenyl]azanium dichloride
SMILES: C1=CC(=C(C=C1[As]=[As]C2=CC(=C(C=C2)O)[NH3+])[NH3+])O.[Cl-].[Cl-]
InChIKey: VLAXZGHHBIJLAD-UHFFFAOYSA-N
Polar surface area: 95.7 Å²
H-bond donors: 4
H-bond acceptors: 4
Formal charge: 0

via PubChem

Research

543 papers

Arsphenamine encephalopathy.Bulletin. Charlotte, N. C. Charlotte Memorial Hospital · 1946
Antimicrobial Chemotherapy.1996
Syphilis and Salvarsan.The British journal of general practice : the journal of the Royal College of General Practitioners · 2019
Arsphenamine jaundice and the recognition of instrument-borne virus infection.Genitourinary medicine · 1995
DRUG-INDUCED THROMBOCYTOPENIA.The Medical annals of the District of Columbia · 1964

via PubMed

~4 min read

Encyclopedic overview

4 sections

Contents

History
Structure
See also
References

thumb|right|300px|The structure of arsphenamine has been proposed to be akin to azobenzene (A). Salvarsan is now assumed to be a mixture of the trimer (B) and the pentamer (C).

Arsphenamine, also known as Salvarsan or compound 606, is an antibiotic drug that was introduced at the beginning of the 1910s as the first effective treatment for the deadly infectious diseases syphilis, relapsing fever, and African trypanosomiasis. This organoarsenic compound was the first modern antimicrobial agent.

Excerpted from Wikipedia’s “arsphenamine” article, available under the CC BY-SA 4.0 licence.