1.0 2011-09-21 00:34:58 UTC 2015-07-21 06:57:52 UTC FDB023805 Norbolethone Norbolethone is a 19-nor anabolic steroid first synthesized in 1966. During the 1960s it was administered to humans in efficacy studies concerned with short stature and underweight conditions. It has never been reported by doping control laboratories prior to 2001. Norbolethone was identified in two urine samples from one athlete by matching the mass spectra and chromatographic retention times with those of a reference standard. The samples also contained at least one likely metabolite. The samples were also unusual because the concentrations of endogenous steroids were exceptionally low. Since norbolethone is not known to be marketed by any pharmaceutical company, a clandestine source of norbolethone may exist. Norbolethone matches the description for what is described as a "designer steroid." Androgenic anabolic steroids (AAS) are defined as natural, synthetic or semi-synthetic drugs chemicals derived from testosterone, used with the aim to improve physical performance by increasing both muscle strength and mass. Despite their reported toxicological effects on the cardiovascular, hepatic and neuro-endocrine systems, the AAS have been extensively used in sports activities. (PMID: 12112254) [HMDB] (+/-)-13-ethyl-17-hydroxy-18,19-Dinor-17a-pregn-4-en-3-one (+/-)-13,17a-Diethyl-17b-hydroxygon-4-en-3-one (+/-)-13b,17a-Diethyl-17b-hydroxygon-4-en-3-one (+/-)-17a-Ethyl-18-homo-19-nortestosterone (17a)-(+/-)-13-ethyl-17-hydroxy-18,19-Dinorpregn-4-en-3-one 13-ethyl-17-hydroxy-18,19-dinor-17a-pregn-4-en-3-one dl-13,17a-Diethyl-17-hydroxygon-4-en-3-one DL-13,17a-Diethyl-17b-hydroxygon-4-en-3-one dl-17b-Hydroxy-13b,17a-diethylgon-4-en-3-one DL-Norbolethone Genabol Wy 3475 C21H32O2 316.4776 316.240230268 (1S,2R,10R,11S,14S,15S)-14,15-diethyl-14-hydroxytetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one norbolethone 1235-15-0 [H][C@@]12CC[C@@](O)(CC)[C@@]1(CC)CC[C@]1([H])[C@@]3([H])CCC(=O)C=C3CC[C@@]21[H] InChI=1S/C21H32O2/c1-3-20-11-9-17-16-8-6-15(22)13-14(16)5-7-18(17)19(20)10-12-21(20,23)4-2/h13,16-19,23H,3-12H2,1-2H3/t16-,17+,18+,19-,20-,21-/m0/s1 FTBJKONNNSKOLX-XUDSTZEESA-N belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety. Gluco/mineralocorticoids, progestogins and derivatives Organic compounds Lipids and lipid-like molecules Steroids and steroid derivatives Pregnane steroids Aliphatic homopolycyclic compounds 17-hydroxysteroids 3-oxo delta-4-steroids Cyclic alcohols and derivatives Cyclohexenones Delta-4-steroids Hydrocarbon derivatives Organic oxides Tertiary alcohols 17-hydroxysteroid 3-oxo-delta-4-steroid 3-oxosteroid Alcohol Aliphatic homopolycyclic compound Carbonyl group Cyclic alcohol Cyclic ketone Cyclohexenone Delta-4-steroid Hydrocarbon derivative Hydroxysteroid Ketone Organic oxide Organic oxygen compound Organooxygen compound Oxosteroid Progestogin-skeleton Tertiary alcohol Solid logp 4.02 ALOGPS logs -4.51 ALOGPS solubility 9.81e-03 g/l ALOGPS logp 4.31 ChemAxon pka_strongest_acidic 19.28 ChemAxon pka_strongest_basic -0.13 ChemAxon iupac (1S,2R,10R,11S,14S,15S)-14,15-diethyl-14-hydroxytetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one ChemAxon average_mass 316.4776 ChemAxon mono_mass 316.240230268 ChemAxon smiles [H][C@@]12CC[C@@](O)(CC)[C@@]1(CC)CC[C@]1([H])[C@@]3([H])CCC(=O)C=C3CC[C@@]21[H] ChemAxon formula C21H32O2 ChemAxon inchi InChI=1S/C21H32O2/c1-3-20-11-9-17-16-8-6-15(22)13-14(16)5-7-18(17)19(20)10-12-21(20,23)4-2/h13,16-19,23H,3-12H2,1-2H3/t16-,17+,18+,19-,20-,21-/m0/s1 ChemAxon inchikey FTBJKONNNSKOLX-XUDSTZEESA-N ChemAxon polar_surface_area 37.3 ChemAxon refractivity 93.72 ChemAxon polarizability 38.16 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 2 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 14990 Specdb::CMs 38937 Specdb::CMs 158404 Specdb::MsMs 299212 Specdb::MsMs 299213 Specdb::MsMs 299214 Specdb::MsMs 341161 Specdb::MsMs 341162 Specdb::MsMs 341163 Specdb::MsMs 2312105 Specdb::MsMs 2312106 Specdb::MsMs 2312107 Specdb::MsMs 2651066 Specdb::MsMs 2651067 Specdb::MsMs 2651068 HMDB06026 #<Reference:0x000055ce300b6680>