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Aminoguanidine is the chemical compound with the formula NH2C(=NH)NHNH2. It is a versatile synthetic intermediate.[3]

Aminoguanidine was studied as an investigational drug for the treatment of diabetic nephropathy, under the nonproprietary name Pimagedine, but never left the clinical trial phase due to side effects.[4]

Chemistry

Synthesis

The industrial synthesis uses the reaction between cyanamide and hydrazine in aqueous solution.[3]

The compound can also be obtained from the reduction of nitroguanidine with zinc in acetic acid.[2]

Properties

Aminoguanidine is a colorless solid that is soluble in water and ethanol. It is basic, producing salts when reacted with organic acids. As established by many crystallographic studies, protonation of aminoguanidine occurs at the imino nitrogen.[5][additional citation(s) needed]

With formic acid, condensation occurs, leading to cyclization to give 3-amino-1,2,4-triazole.[3]

The compound reacts with nitrous acid in acidic medium to give 5-aminotetrazole via the intermediate guanylazide.[3]

At neutral pH, the reaction leads to tetrazene.[6] Diazotization in acetic acid yields 1,3-di-(tetrazolyl)-triazene.[3]

Investigational drug

Pimagedine was investigated as a drug for kidney disease by the pharmaceutical company Alteon, but safety issues that appeared during clinical trials ended development before it was marketed and financial support was dropped for further trials.[7][4]

References

  1. ^ Haynes, William M., ed. (2016). CRC Handbook of Chemistry and Physics (97th ed.). Boca Raton, Florida: CRC Press. pp. 3–302. ISBN 9781498754293.
  2. ^ a b Smith, G. B. L.; Anzelmi, Edward (1935-12-01). “Reduction of Nitroguanidine. III. Synthesis of Aminoguanidine”. Journal of the American Chemical Society. 57 (12): 2730. Bibcode:1935JAChS..57.2730S. doi:10.1021/ja01315a510. ISSN 0002-7863.
  3. ^ a b c d e Güthner, Thomas; Mertschenk, Bernd; Schulz, Bernd (2006). “Guanidine and Derivatives”. Ullmann’s Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a12_545.pub2. ISBN 978-3-527-30673-2.
  4. ^ a b “Alteon Shares Plummet On Poor Pimagedine Test Results”. San Diego Source. 16 November 1998. Archived from the original on 2013-03-13. Retrieved 14 May 2026.
  5. ^ Adams, J. M. (1977). “The Crystal Structure of Aminoguanidinium Dihydrogen Orthophosphate”. Acta Crystallographica Section B Structural Crystallography and Crystal Chemistry. 33 (5): 1513–1515. Bibcode:1977AcCrB..33.1513A. doi:10.1107/S0567740877006402.
  6. ^ Patinkin, Seymour H.; Horwitz, Jerome P.; Lieber, Eugene (1955-02-01). “The Structure of Tetracene1,2”. Journal of the American Chemical Society. 77 (3): 562–567. Bibcode:1955JAChS..77..562P. doi:10.1021/ja01608a014. ISSN 0002-7863.
  7. ^ Harry Keen; JH Fukker; G Menzinger (July 19, 1997). “Early closure of European Pimagedine trial”. The Lancet. 350 (9072). PlumX Metrics: 214–215. doi:10.1016/S0140-6736(97)26029-0. PMID 9250200. S2CID 54316555.