Title: Noformicin
CAS Registry Number: 155-38-4
CAS Name: 5-Amino-N-(3-amino-3-iminopropyl)-3,4-dihydro-2H-pyrrole-2-carboxamide
Additional Names: N-(2-amidinoethyl)-5-imino-2-pyrrolidinecarboxamide; 2-[N-(2-amidinoethyl)carbamoyl]-5-iminopyrrolidine; b-(5-imino-2-pyrrolidinecarboxamido)propamidine; noformycin
Molecular Formula: C8H15N5O
Molecular Weight: 197.24
Percent Composition: C 48.72%, H 7.67%, N 35.51%, O 8.11%
Literature References: Antiviral agent produced by Nocardia formica, culture no. N.R.R.L. 2470: Peck et al., US 2804463 (1957 to Merck & Co.); Gray, Phytopathology 45, 281 (1955). Activity studies: Furusawa et al., Proc. Soc. Exp. Biol. Med. 116, 938 (1964); eidem, Med. Pharmacol. Exp. 12, 259 (1965). Synthesis of (+)- and (±)-forms: Diana, J. Med. Chem. 16, 857 (1973).
Derivative Type: (+)-Form dihydrochloride
Molecular Formula: C8H17Cl2N5O
Molecular Weight: 270.16
Percent Composition: C 35.57%, H 6.34%, Cl 26.25%, N 25.92%, O 5.92%
Properties: The biologically active form. Crystals from methanol, dec 263-264°. [a]D25 +8.8° (methanol). Sol in water. Somewhat sol in organic solvents. pKa 9.4.
pKa: pKa 9.4
Optical Rotation: [a]D25 +8.8° (methanol)
Derivative Type: (±)-Form dihydrochloride
Properties: mp 252-254°.
Melting point: mp 252-254°
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