ψ 
Spin Labels 
Molecules which contain an atom or a group of atoms exhibiting an unpaired electron spin that can be detected by electron spin resonance spectroscopy and can be bonded to another molecule. (McGraw-Hill Dictionary of Chemical and Technical Terms, 4th ed)  /chem syn permitted   
See Also Electron Spin Resonance Spectroscopy; Spin Trapping		Other names Labels, Spin
 
SubstanceCAS Registry & nameCategoriesSourceDrugs*
5,5-dimethyl-1-pyrroline-1-oxide  3317-61-1   *Cyclic N-Oxides Spin Labels.  Biochem Biophys Res Commun 83(1):69;1978
tempol  2226-96-2 2,2,6,6-tetramethyl-4-piperidinol-N-oxyl  *Cyclic N-Oxides *Spin Labels Drug Synergism Spin Labels. 
Pharma Action Antioxidants ; Protein Synthesis Inhibitors ; Radiation-Protective Agents ; Neuroprotective Agents 		Biochemistry 14(13):2793;1975; Cell Survival Low Doses Radiat W3GR35:1974e; Int J Radiat Biol 22(2):115;1972; J Am Chem Soc 97(6):1388;1975; J Supramol Struct 2(5-6):609;1974; Proc Natl Acad Sci USA 1980;77(2):790
phenyl-N-tert-butylnitrone  3376-24-7   *Cyclic N-Oxides Spin Labels Free Radical Scavengers. 
Pharma Action Neuroprotective Agents 		Arch Biochem Biophys 180:480;1977; Biochim Biophys Acta 539(3):402;1978; FEBS Lett 1980;122(2):303
TEMPO  2564-83-2   *Cyclic N-Oxides Spin Labels. 
Pharma Action Antioxidants 		Anesthesiology 38(3):207;1973; Biochem Pharmacol 26:675;1977; Biochim Biophys Acta 465(3):466;1977; J Membr Biol 40:315;1978; Radiat Res 69:489;1977
5-doxylstearic acid  29545-48-0   *Cyclic N-Oxides Spin Labels.  Biochim Biophys Acta 311(2):141;1973; Can J Biochem 55(2):173-86;1977; Chem Phys Lipids 17(2-3):213;1976; J Lipid Res 19(7):841;1978
alpha-(4-pyridyl-1-oxide)-N-tert-butylnitrone  0   *Pyridines Spin Labels.  Radiat Res 1984;100(2):222
4-maleimido-2,2,6,6-tetramethylpiperidinooxyl  15178-63-9   *Cyclic N-Oxides Spin Labels.  FEBS Lett 97(2):363;1979; J Biol Chem 253(13):4642;1978
16-nitroxystearic acid  53034-38-1   *Cyclic N-Oxides Spin Labels.  Biochim Biophys Acta 1981;647(2):196
N-methyl-D-glucamine dithiocarbamate  91840-27-6 D-Glucitol, 1-deoxy-1-((dithiocarboxy)methylamino)-, monosodium salt  *Thiocarbamates Sorbitol/*analogs & derivatives Spin Labels. 
Pharma Action Iron Chelating Agents 		Acta Pharmacol Toxicol (Copenh) 1984;54(3):189
tetracyanoquinodimethane  1518-16-7   *Nitriles Spin Labels.  Dokl Akad Nauk SSSR 240(2):463;1978; FEBS Lett 69(1):252;1976
3,5-dibromo-4-nitrosobenzenesulfonate  83016-63-1   *Benzenesulfonates *Nitroso Compounds Spin Labels.  Biochem Biophys Res Commun 1986;136(2):657
5-diethoxyphosphoryl-5-methyl-1-pyrroline N-oxide  157230-67-6   *Cyclic N-Oxides Spin Labels.  J Biol Chem 1996 Mar 15;271(11):6000-9
tert-nitrosobutane  917-95-3   *Nitroso Compounds Spin Labels.  Int J Radiat Biol 1982;41(4):435
tempamine  14691-88-4 4-amino-2,2,6,6-tetramethyl-1-piperidinyloxy  *Cyclic N-Oxides Spin Labels.  Arch Biochem Biophys 194(1):138;1979; Biochem Biophys Res Commun 77(4):1486;1977; Carbohydr Res 75:11;1979
12-doxylstearic acid  29545-47-9   *Cyclic N-Oxides Spin Labels.  J Biol Chem 1983;258(5):2929
lithium phthalocyanine  111716-29-1   *Indoles *Organometallic Compounds Lithium Spin Labels.  Proc Natl Acad Sci USA 1993 Jun 15;90(12):5438-42
3-fluorotyrosine  139-26-4   Tyrosine/*analogs & derivatives Spin Labels. 
Pharma Action Central Nervous System Stimulants 		Biochemistry 17(18):3860;1978
2,2,5,5-tetramethyl-1-pyrrolidinyloxy-3-carboxylic acid  2154-68-9   *Cyclic N-Oxides Spin Labels. 
Pharma Action Radiation-Sensitizing Agents 		Int J Radiat Biol 1981;40(4):451
2,2,6,6-tetramethylpiperidine-N-oxide-4-amino-4-carboxylic acid  15871-57-5 1-Piperidinyloxy, 4-amino-4-carboxy-2,2,6,6-tetramethyl  *Cyclic N-Oxides Spin Labels.  Biochim Biophys Acta 1983;742(1):63
3-carbamoyl-2,2,5,5-tetramethyl-3-pyrroline-1-yloxyl  3229-73-0   *Cyclic N-Oxides Spin Labels.  Biochim Biophys Acta 1985;821(2):259
galvinoxyl  2370-18-5 4-((3,5-bis(1,1-dimethylethyl)-4-oxo-2,5-cyclohexadien-1-ylidene)methyl)-2,6-bis(1,1-dimethyl ethyl)phenoxy  *Benzhydryl Compounds Spin Labels.  Anal Biochem 94(2):322;1979
(1-oxyl-2,2,5,5-tetramethylpyrroline-3-methyl)methanethiosulfonate  81213-52-7 1H-Pyrrol-1-yloxy, 2,5-dihydro-2,2,5,5-tetramethyl-3-(((methylsulfonyl)thio)methyl)  *Cyclic N-Oxides *Mesylates Spin Labels.  Anal Biochem 1982;119(2):450
N-(1-oxyl-2,2,6,6-tetramethyl-4-piperidinyl)iodoacetamide  25713-24-0   *Cyclic N-Oxides Spin Labels. 
allocolchicine  641-28-1   Colchicine/*analogs & derivatives Spin Labels.  Acta Chem Scand (B) 1981;35(10):677
N-(1-oxyl-2,2,5,5-tetramethyl-3-pyrrolidinyl)maleimide  5389-27-5 1-Pyrrolidinyloxy, 3-(2,5-dihydro-2,5-dioxo-1H-pyrrol-1-yl)-2,2,5,5-tetramethyl  *Cyclic N-Oxides Spin Labels.  Can J Biochem 1979;57(12):1407
5,5-dimethyl-5-hydroperoxy-1-pyrrolidinyloxy  85963-89-9   *Cyclic N-Oxides Spin Labels.  Biochim Biophys Acta 1988;969(3):236
3,3,5,5-tetramethyl-1-pyrroline N-oxide  10135-38-3   *Cyclic N-Oxides Spin Labels.  Biochem J 1986;240(3):789
tempocholine  50669-92-6 1-Piperidinyloxy, 4-((2-hydroxyethyl)dimethylammonio)-2,2,6,6-tetramethyl  *Cyclic N-Oxides Spin Labels.  FEBS Lett 89(1):29;1978; J Biochem (Tokyo) 83:1299;1978
3-oxo-androstan-17-yl-(2'',2'',6'',6''-tetramethyl-N-oxyl)piperidyl butan-1',4'-dioate  0   Spin Labels *Androstanes.  Indian J Biochem Biophys 2000 Feb;37(1):45-50
4-(N,N,N-trimethylamino)-2,2,6,6-tetramethylpiperidine-1-oxyl  64486-64-2   *Cyclic N-Oxides Spin Labels.  Radiology 1987;163(1):239
3,4-dihydro-3,3-dimethylisoquinoline-N-oxide  0   *Isoquinolines Spin Labels.  Ann N Y Acad Sci 1994 Nov 17;738:243-9
MCPROXYL  0   *Cyclic N-Oxides *Pyrrolidines Spin Labels.  FEBS Lett 1997 Dec 8;419(1):99-102
di-t-butyl nitroxide  2406-25-9   *Butanes Spin Labels.  Biochem Biophys Acta 406(2):197;1975; J Am Chem Soc 99(13):4299;1977; J Membrane Biol 40(4):319;1978; Proc Nat Acad Sci USA 71(2):474;1974
5,5-dimethylpyrrolidin-2-one-1-oxide  0   *Cyclic N-Oxides Spin Labels.  Mol Pharmacol 1980;17(2):233
norpseudopelleterine-N-oxyl  7123-92-4   *Cyclic N-Oxides Spin Labels.  Br J Cancer 37(Suppl 3):42;1978; Br J Cancer 37(Suppl 3):73;1978; Int J Radiat Biol 22(2):115;1972; Radiat Res 69:489;1977; Radiat Res 75(1):54;1978
3-doxylcholestane  18353-76-9   *Cyclic N-Oxides Spin Labels.  Biochim Biophys Acta 290(1):32;1972
3-(2-iodoacetamido)-2,2,5,5-tetramethyl-1-pyrrolidinyloxyl  27048-01-7   *Cyclic N-Oxides Spin Labels.  Ann NY Acad Sci 1980;356:20
N-tert-butylhydroxylamine  16649-50-6   *Hydroxylamines Spin Labels.  Free Radic Res Commun 1991;14(5-6):395-407
2-ethoxycarbonyl-2-methyl-3,4-dihydro-2H-pyrrole-1-oxide  0   Spin Labels *Pyrroles.  Free Radic Biol Med 2000 Feb 1;28(3):403-8
tempo carboxylic acid  37149-18-1   *Cyclic N-Oxides Spin Labels.  Eur J Radiol 1986;6(1):48
proxyl nitroxide  3229-53-6 1-Pyrrolidinyloxy, 2,2,5,5-tetramethyl  *Cyclic N-Oxides Spin Labels.  J Am Chem Soc 98(10):3052;1976
bis(sulfo-N-succinimidyl)doxyl-2-spiro-4'-pimelate  102260-45-7   *Succinimides Spin Labels.  Biochemistry 1986;25(13):3824
7-doxylstearic acid  40951-82-4   *Cyclic N-Oxides Spin Labels.  Biochim Biophys Acta 1988;939(2):393
1-hydroxy-2,2,6,6-tetramethyl-4-oxopiperidine  3637-11-4   *Piperidines Spin Labels.  Biochem Biophys Res Commun 1997 Jan 3;230(1):54-7
(N-dithiocarboxysarcosine)iron(III)  0   *Ferric Compounds *Thiocarbamates Spin Labels.  Eur J Biochem 1999 Dec;266(3):771-7
N-(2,2,6,6-tetramethylpiperidyl-1-oxyl) N'- (cyclohexyl)carbodiimide  42249-40-1 1-Piperidinyloxy, 4-((cyclohexylcarbonimidoyl)amino)-2,2,6,6-tetramethyl  *Cyclic N-Oxides Spin Labels.  J Biol Chem 250(13):5020;1975
2-(16'-(N-oxyl-4',4'-dimethyloxazolidine)stearoyl)phosphatidylcholine  0   *Cyclic N-Oxides Spin Labels.  Can J Biochem 1980;58(2):143
tempo 4-bromoacetamide  24567-97-3   *Cyclic N-Oxides Spin Labels.  Biochemistry 1980;19(22):5140
3-(bis-(2-chloroethyl)carbohydrazide)-2,2,5,5-tetramethylpyroline-1-oxyl  67128-86-3 1H-Pyrrol-1-yloxy, 3-((2,2-bis(2-chloroethyl)hydrazino)carbonyl)-2,5-dihydro-2,2,5,5-tetramethyl  *Cyclic N-Oxides Spin Labels.  Biochem Pharmacol 1981;30(4):289
4-(dodecyldimethylammonium)-1-oxyl-2,2,6,6-tetramethylpiperidine  31645-23-5 1-Piperidinyloxy, 4-(dodecyldimethylammonio)-2,2,6,6-tetramethyl-, bromide  *Cyclic N-Oxides Spin Labels.  Biochem Biophys Res Commun 1981;100(3):1137
2-(N-methyl-N-(2,2,6,6-tetramethylpiperidinooxyl))ethyl 4-hexyloxybenzoate  0   *Cyclic N-Oxides Spin Labels.  Biochim Biophys Acta 1984;770(1):55
N-(1-methyldodecyl)-N,N,N-trimethylammonium  52234-85-2   *Quaternary Ammonium Compounds Spin Labels.  Gen Physiol Biophys 1989;8(2):133
1-palmitoyl-2-(16-doxystearoyl)phosphatidylcholine  63321-67-5   *Cyclic N-Oxides *Phosphatidylcholines Spin Labels.  Biophys J 1991;59(4):950
adenosine 5'-O-(S-acetamidoproxyl 3-thiotriphosphate)  0   *Cyclic N-Oxides Adenosine Triphosphate/*analogs & derivatives Spin Labels Thionucleotides.  Biochemistry 1995 Nov 21;34(46):15068-74
5-ethoxycarbonyl-5-methyl-1-pyrroline N-oxide  0   Spin Labels *Cyclic N-Oxides.  FEBS Lett 2000 May 4;473(1):58-62
12-doxylstearate methyl ester  29639-21-2 3-Oxazolidinyloxy, 2-hexyl-2-(11-methoxy-11-oxoundecyl)-4,4-dimethyl  *Cyclic N-Oxides Spin Labels.  J Biol Chem 1980;255(8):3330
3'-O-(1-oxyl-2,2,5,5-tetramethyl-3-carbonyl pyrrolidine)-adenosine 5'-triphosphate  74014-72-5 Adenosine 5'-(tetrahydrogen triphosphate), 3'-(2,2,5,5-tetramethyl-1-oxy-3-pyrrolidinecarboxylate)  Adenosine Triphosphate/*analogs & derivatives Spin Labels.  Biochim Biophys Acta 1980;601(1):34
1-oxyl-2,2,6,6-tetramethyl 4-piperidinyl nicotinate  52286-91-6 1-Piperidinyloxy, 2,2,6,6-tetramethyl-4-((3-pyridinylcarbonyl)oxy)  *Cyclic N-Oxides Spin Labels.  J Biol Chem 1982;257(10):5372
N-methylmaleimide nitroxide  54060-41-2 1-Pyrrolidinyloxy, 3-((2,5-dihydro-2,5-dioxo-1H-pyrrol-1-yl)methyl)-2,2,5,5-tetramethyl  *Maleimides Spin Labels.  Biochim Biophys Acta 1982;687(2):257
2,2,5,5-tetramethyl-1-oxy-3-pyrroline-3-carboxylic acid  2154-67-8 1H-Pyrrol-1-yloxy, 3-carboxy-2,5-dihydro-2,2,5,5-tetramethyl  *Cyclic N-Oxides Spin Labels.  Biochemistry 1983;22(8):1941
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