19NorDehydroepiandrosterone

19NorDehydroepiandrosterone (19NorDHEA) or better written as NorAndrostene-3b-ol,17-one is a naturally occurring C18 hormone in many mammals. It has been shown to exist in pigs and humans in direct papers that show 19NorSteroids being produced by various tissues and enzymes. The theory behind 19NorDHEA occurring in pigs and humans is via the conversion of 19NorAndrostenedione, 19NorAndrostenediol and Nandrolone [Reznik Y, Dehennin L, Coffin C, Mahoudeau J, Leymarie P. Urinary nandrolone metabolites of endogenous origin in man: a confirmation by output regulation under human chorionic gonadotropin stimulation. J Clin Endocrinol Metab. Jan;86(1):146-50, 2001] [Le Bizec B, Gaudin I, Monteau F, Andre F, Impens S, De Wasch K, De Brabander H. Consequence of boar edible tissue consumption on urinary profiles of nandrolone metabolites. I. Mass spectrometric detection and quantification of 19-norandrosterone and 19-noretiocholanolone in human urine. Rapid Commun Mass Spectrom. 14(12):1058-65, 2000] [Le Bizec B, Monteau F, Gaudin I, Andre F. Evidence for the presence of endogenous 19-norandrosterone in human urine. J Chromatogr B Biomed Sci Appl. Feb 19;723(1-2):157-72, 1999] [Dehennin L, Bonnaire Y, Plou P. Urinary excretion of 19-norandrosterone of endogenous origin in man: quantitative analysis by gas chromatography-mass spectrometry. J Chromatogr B Biomed Sci Appl. Jan 22;721(2):301-7, 1999] [Debruyckere G, Van Peteghem C. Detection of 19-nortestosterone and its urinary metabolites in miniature pigs by gas chromatography-mass spectrometry. J Chromatogr. Apr 5;564(2):393-403, 1991] [Van Eenoo P, Delbeke FT, de Jong FH, De Backer P. Endogenous origin of norandrosterone in female urine: indirect evidence for the production of 19-norsteroids as by-products in the conversion from androgen to estrogen. J Steroid Biochem Mol Biol. Oct;78(4):351-7, 2001] [De Wasch K, Le Bizec B, De Brabander H, Andre F, Impens S. Consequence of boar edible tissue consumption on urinary profiles of nandrolone metabolites. II. Identification and quantification of 19-norsteroids responsible for 19-norandrosterone and 19-noretiocholanolone excretion in human urine. Rapid Commun Mass Spectrom. 15(16):1442-7, 2001] .

This interconversion happens via 17bHydroxysteroid-Dehydrogenase and 3a/b-Hydroxysteroid-Dehydrogenase. Additionally, there is some suggested direct conversion via the partial aromatization of DHEA which is proven to happen in humans (and presumably other mammals) to create C18 androgens. [Milewich L, Hendricks TS, Johnson AR. Metabolism of dehydroisoandrosterone and androstenedione in human pulmonary endothelial cells in culture. J Clin Endocrinol Metab. May;56(5):930-5, 1983] [Numazawa M, Nagaoka M, Sohtome N. Aromatase reaction of 3-deoxyandrogens: steric mode of the C-19 oxygenation and cleavage of the C10-C19 bond by human placental aromatase. Biochemistry. Aug 16;44(32):10839-45, 2005] 19NorDHEA should exist in several isomers including 3-alpha and 3-beta hydroxy configurations and both 4-ene and 5-ene variants.

As a dietary supplement, 19NorDHEA can be used in combination and substitution to standard 5-DHEA supplementation to potentiate the beneficial effects from increased levels of adrenal androgens. It has some obvious benefits over DHEA in safety and potency. First, 19Nor-Dihydro-Testosterone (a natural metabolite via 5aReductase) is much less potent than standard dihydrotestosterone in potency and therefor should have less virulizing aspects in men and women, such as hair loss and prostate stimulation. [Vida, J. Androgens and Anabolic Agents. Worchester Foundation For Experimental Biology, Shrewsbury, Massacheusetts 1969] This effect makes 19NorDHEA a more effective agent for muscle wasting with less side effects. Additionally nandrolone, another metabolite of 19NorDHEA, is 120% as potent as testosterone for building muscle, giving 19NorDHEA a more potent anabolic profile potential with less of the negative virulizing effects seen with standard DHEA supplementation. [Vida, J. Androgens and Anabolic Agents. Worchester Foundation For Experimental Biology, Shrewsbury, Massacheusetts 1969]

References