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149934-16-79-Nitro Minocycline

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Catalogue No.:	VE0022245
CAS No.:	149934-16-7
Mol. Formula:	C23H26N4O9
Mol. Weight:	502.47 g/mol

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Additional information on CAS 149934-16-7

Parent drug

Minocycline

IUPAC Name

(4S,4aS,5aR,12aS)-4,7-Bis(dimethylamino)-3,10,12,12a-tetrahydroxy-9-nitro-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide

Smiles

O=C(C1=C(O)[C@@H](N(C)C)[C@@](C[C@@]2([H])C(C(C3=C(O)C([N+]([O-])=O)=CC(N(C)C)=C3C2)=O)=C4O)([H])[C@@]4(O)C1=O)N

InChI

InChI=1S/C23H26N4O9/c1-25(2)11-7-12(27(35)36)17(28)14-9(11)5-8-6-10-16(26(3)4)19(30)15(22(24)33)21(32)23(10,34)20(31)13(8)18(14)29/h7-8,10,16,28,30-31,34H,5-6H2,1-4H3,(H2,24,33)/t8-,10-,16-,23-/m0/s1

Pharmacopoeial Synonyms

N/A

Other Synonyms

N/A

Description

9-Nitro Minocycline (CAS 149934-16-7) is a nitroaromatic tetracycline impurity derived from minocycline, consistent with oxidative nitration of the aromatic D-ring or related process-side reactions during manufacture and storage. With molecular formula C23H26N4O9 and molecular weight 502.47 g/mol, it preserves the polycyclic tetracycline scaffold while introducing a strongly electron-withdrawing nitro substituent that can alter UV response, ionization behavior, and chromatographic retention. Its occurrence is assessed under impurity control strategies because nitroaromatic entities may warrant toxicological scrutiny. Characterization typically relies on LC-MS/MS, high-resolution LC-MS, and photodiode array LC methods, with structural confirmation by NMR when isolated.