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Record Information
StatusExpected but not Quantified
Creation Date2006-08-13 22:34:37 UTC
Update Date2019-01-11 19:18:06 UTC
Secondary Accession Numbers
  • HMDB04626
Metabolite Identification
Common NameTetrahydrogestrinone
DescriptionThe identification of tetrahydrogestrinone (THG), the first true "designer androgen," as a sports doping agent reflects both an alarmingly sophisticated illicit manufacturing facility and an underground network of androgen abusers in elite sports, as well as the still untapped potential for designer androgens in medicine. Never marketed, THG was apparently developed as a potent androgen that was undetectable by conventional International Olympic Committee-mandated urinary sports doping tests. As a potent androgen and progestin with unspecified contaminants, its distribution for use at high doses without any prior biological or toxicological evaluation poses significant health risks. Yet this diversion of science also highlights the prospect of designer androgens for use in human medicine. Designer androgens also offer the possibility of tissue-specific effects enhancing the beneficial effects of androgens while mitigating the undesirable ones. Further developments require better understanding of the post receptor tissue selectivity of androgens, comparable to the mechanism underlying that of partial estrogen agonists (SERMs). This experience highlights the ongoing need for vigilance to detect novel drug doping strategies in order to maintain fairness and safety in elite sports. This will require the deployment of generic catch-all tests, such as sensitive and specific in vitro androgen bioassays, coupled with the development of mass spectrometry-based tests for specific doping agents. Starting from gestrinone, chemists can synthesize THG in one reaction step. (PMID: 15934041 , 15292520 ).
Chemical FormulaC21H28O2
Average Molecular Weight312.4458
Monoisotopic Molecular Weight312.20893014
IUPAC Name(10S,11S,14S,15S)-14,15-diethyl-14-hydroxytetracyclo[²,⁷.0¹¹,¹⁵]heptadeca-1,6,16-trien-5-one
Traditional Nametetrahydrogestrinone
CAS Registry Number618903-56-3
InChI Identifier
Chemical Taxonomy
Description belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassEstrane steroids
Direct ParentEstrogens and derivatives
Alternative Parents
  • Estrogen-skeleton
  • 3-oxosteroid
  • Hydroxysteroid
  • 17-hydroxysteroid
  • Oxosteroid
  • Cyclohexenone
  • Cyclic alcohol
  • Tertiary alcohol
  • Cyclic ketone
  • Ketone
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Alcohol
  • Organooxygen compound
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available

Route of exposure:


Biological location:


Naturally occurring process:


Biological role:

Industrial application:

Physical Properties
Experimental Properties
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
Water Solubility0.02 g/LALOGPS
pKa (Strongest Acidic)18.9ChemAxon
pKa (Strongest Basic)-0.14ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity95.42 m³·mol⁻¹ChemAxon
Polarizability37.02 ųChemAxon
Number of Rings4ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-1190000000-df8a155fb516cec4576aJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0a4i-2029000000-895175c474d195f98cc4JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ot-0095000000-8cbb62095c5e14373a79JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01ot-0191000000-e69b0d42106f07a3727cJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0umi-1490000000-96c8e821e03405188c49JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0029000000-c002fd210563a9508a67JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0089000000-1b89e06ba01d60280bddJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00lr-0090000000-e424a28e9a87e909dcf0JSpectraViewer | MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB06870
Phenol Explorer Compound IDNot Available
FoodDB IDFDB023385
KNApSAcK IDNot Available
Chemspider ID5257020
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6857686
ChEBI IDNot Available
Synthesis ReferenceLabrie, Fernand; Luu-The, Van; Calvo, Ezequiel; Martel, Celine; Cloutier, Julie; Gauthier, Sylvain; Belleau, Pascal; Morissette, Jean; Levesque, Marie-Helene; Labrie, Claude. Tetrahydrogestrinone induces a genomic signature typical of a potent anabolic steroid. J Endocrinol. 2005 Feb;184(2):427-33. Pubmed: 15684350
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Thevis M, Geyer H, Mareck U, Schanzer W: Screening for unknown synthetic steroids in human urine by liquid chromatography-tandem mass spectrometry. J Mass Spectrom. 2005 Jul;40(7):955-62. [PubMed:15934041 ]
  2. Handelsman DJ: Designer androgens in sport: when too much is never enough. Sci STKE. 2004 Jul 27;2004(244):pe41. [PubMed:15292520 ]