Reaction SMILES: [OH:1][C@:2]1(C)[CH2:19][CH2:18][C@@:17]2([CH3:20])[C@@H:4]([CH2:5][CH2:6][C@@H:7]3[C@@H:16]2[CH2:15][CH2:14][C@@:12]2([CH3:13])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[N+:21]([O-:23])=[O:22])[CH2:3]1.CN(C1C=CC([C@H]2C[C@@]3(C)[C@@H](CC[C@@H]3[N+]([O-])=O)[C@H]3[C@H]2[C@@H]2[C@@H](CC3)C[C@@](O)(C)CC2)=CC=1)C.[N+]([C@H]1CC[C@H]2[C@H]3[C@H](CC[C@]12C)[C@]1(C)[C@H](C[C@@H](O)CC1)CC3)([O-])=O.C(N[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@]12C)[C@]1(C)[C@H](C[C@H](O)CC1)CC3)(=O)C.O=C(N[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@]12C)[C@]1(C)[C@H](C[C@H](O)CC1)CC3)CC.O[C@@H]1CC[C@@]2(C)[C@@H](CC[C@@H]3[C@@H]2CC[C@@]2(C)[C@H]3CCC2=S)C1.O[C@@H]1CC[C@@]2(C)[C@@H](CC[C@@H]3[C@@H]2CC[C@@]2(C)[C@H]3CC[C@@H]2S)C1.O[C@@H]1CC[C@@]2(C)[C@@H](CC[C@@H]3[C@@H]2CC[C@@]2(C)[C@H]3CC=C2C2OC=CC=2)C1.O[C@@H]1CC[C@@]2(C)[C@@H](CC[C@@H]3[C@@H]2CC[C@@]2(C)[C@H]3CC[C@@H]2C2OC=CC=2)C1.N[C@@H]1CC[C@@]2(C)[C@@H](CC[C@@H]3[C@@H]2CC[C@@]2(C)[C@H]3CCC2=O)C1.Cl.N[C@@H]1CC[C@@]2(C)[C@@H](CC[C@@H]3[C@@H]2CC[C@@]2(C)[C@H]3CC[C@@H]2[N+]([O-])=O)C1.Cl.CN(C)[C@@H]1CC[C@@]2(C)[C@@H](CC[C@@H]3[C@@H]2CC[C@@]2(C)[C@H]3CC[C@@H]2[N+]([O-])=O)C1.Cl.C(N[C@@H]1CC[C@@]2(C)[C@@H](CC[C@@H]3[C@@H]2CC[C@@]2(C)[C@H]3CC[C@@H]2[N+]([O-])=O)C1)CCCCC>>[N+:21]([C@H:11]1[CH2:10][CH2:9][C@H:8]2[C@H:7]3[C@H:16]([CH2:15][CH2:14][C@:12]12[CH3:13])[C@:17]1([CH3:20])[C@H:4]([CH2:3][C@H:2]([OH:1])[CH2:19][CH2:18]1)[CH2:5][CH2:6]3)([O-:23])=[O:22]
Reactant: C[C@@]1(O)CC[C@@]2(C)[C@@H](CC[C@@H]3[C@@H]2CC[C@]2(C)[C@@H]([N+](=O)[O-])CC[C@@H]32)C1
Agent: CC(=O)N[C@H]1CC[C@H]2[C@@H]3CC[C@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@]12C
Agent: CCC(=O)N[C@H]1CC[C@H]2[C@@H]3CC[C@H]4C[C@H](O)CC[C@]4(C)[C@H]3CC[C@]12C
Agent: CCCCCCN[C@@H]1CC[C@@]2(C)[C@@H](CC[C@@H]3[C@@H]2CC[C@]2(C)[C@@H]([N+](=O)[O-])CC[C@@H]32)C1
Product: C[C@]12CC[C@@H](O)C[C@@H]1CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H]([N+](=O)[O-])CC[C@@H]12

Procedure:
3α-Hydroxy-3β-methyl-17β-nitro-5α-androstane; 3α-Hydroxy-17β-thiomethyl-5α-androstane; 11β-[4-(N,N-Dimethylamino)phenyl]-3α-hydroxy-3β-methyl-17β-nitro-5 αestrane; 3β-Hydroxy-5α-androstan-17-oxime; 17β-Nitro-5α-androstan-3β-ol; 17β-Nitro-21-nor-23-oxo-17α-cholan-3α-ol; 5′-Methylspiro-[androstan-17β, N-oxido-2′-pyrrolidine]-3α-ol; 5′-Methylspiro-[androstan-17β, 2′-pyrrolidine]-3α-ol; 1′-Formyl-5′-methylspiro-[androstan-17β, 2′-pyrrolidine]-3α-ol; 17β-Nitro-5α-androstan-3α-ol benzoyl ester; 17β-Amino-5α-androstan-3α-ol benzoyl ester; 17β-(Acetylamino)-5α-androstan-3α-ol benzoyl ester; 17β-(Acetylamino)-5α-androstan-3α-ol; 17β-[(1-Oxopropyl)-amino]-5α-androstan-3α-ol benzoyl ester; 17β-[(1-Oxopropyl)-amino]-5α-androstan-3α-ol; 17β-(N-Oxido-2-propaneimine)-5α-androstan-3α-ol; 3α-Hydroxy-5α-androstan-17-thione; 3α-Hydroxy-5α-androstan-17β-thiol; 3α-Hydroxy-5α-androstan-17β-methylsulfoxide (both diatereomers); 3α-Hydroxy-5α-androstan-17β-methylsulfone; 3α-Hydroxy-17-(2-furanyl)-5 αandrost-16-ene; 3α-Hydroxy-17β-(2-furanyl)-5 αandrostane; 11β-[4-(N,N-Dimethylamino)phenyl]-3α-hydroxy-3β-methyl-5α-17β-hydroxy-estrane hydrochloride; 11β-[4-(N,N-Dimethylamino)phenyl]-3α-hydroxy-3β-methyl-5α-estra-17-one hydrochloride; 11β-[4-(N,N-Dimethylamino)phenyl]-3α-hydroxy-3β-methyl-5α-estrane-17-oxime; 11β-[4-(N,N-Dimethyl-N-(oxy)amino)phenyl]-3α-hydroxy-3β-methyl-5α-estrane-17-oxime; 3α-Amino-5α-androstan-17-one; 3α-Amino-17β-nitro-5αandrostane hydrochloride; 3α-Dimethylamino-17β-nitro-5α-androstane hydrochloride; 3α-N-Hexylamino-17β-nitro-5 αandrostane hydrochloride; 3α-N-(3-Phenylpropyl)-17β-nitro-5α-androstane hydrochloride; 3α-Acetamido-5α-17β-nitro-androstane.