Structure via PubChem · Public domain (PubChem)
synthalin A
Sign in to saveAlso known as 1,10-bis(guanidino)decane, decamethylenediguanidine, 1,1'-decamethylenediguanidine, decamethylenebis(guanidine), N,N'''-1,10-Decanediylbisguanidine
Synthalin was an oral anti-diabetic drug. Discovered in 1926 it was marketed in Europe by Schering AG of Berlin as a synthetic drug with insulin-like properties that could be taken orally. However, it was toxic to the liver and kidney and was withdrawn from the market in the early 1940s.
Chemical data
- Formula
- C12H28N6
- Molecular weight
- 256.39 g/mol
- IUPAC name
- 2-[10-(diaminomethylideneamino)decyl]guanidine
- SMILES
- C(CCCCCN=C(N)N)CCCCN=C(N)N
- InChIKey
- OZZMUVKANAPKGI-UHFFFAOYSA-N
- XLogP
- 0.7
- Polar surface area
- 129 Ų
- H-bond donors
- 4
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 256.238
Show 2 more facts
- chemical formula
- C₁₂H₂₈N₆
- canonical SMILES
- C(CCCCCN=C(N)N)CCCCN=C(N)N
Sources (2)
via Wikidata · CC0
~2 min read
Encyclopedic overview
3 sectionsContents
- History
- Anti-trypanosome
- References
Synthalin was an oral anti-diabetic drug. Discovered in 1926 it was marketed in Europe by Schering AG of Berlin as a synthetic drug with insulin-like properties that could be taken orally. However, it was toxic to the liver and kidney and was withdrawn from the market in the early 1940s.
==History== The folk remedy French lilac (Galega officinalis), was used to treat the symptoms of diabetes, and towards the end of the nineteenth century it was discovered to contain galegine, a derivative of guanidine. This had a hypoglycaemic effect but was very toxic to the liver. Karl Slotta at the Chemistry Institute of the University of Vienna synthesized derived compounds that had a polymethylene chain with a guanidine group at each end. These diguanides were less toxic and more potent than guanidine. In 1926, E. Frank, working in Oskar Minkowski's clinic in Wroclaw performed a clinical trial on one of these agents. It was subsequently marketed as Synthalin by Schering AG for treating mild cases of diabetes.
Excerpted from Wikipedia’s “synthalin A” article, available under the CC BY-SA 4.0 licence.