19793-20-5 Usage
Uses
Used in Pharmaceutical Industry:
19-Norandrostenediol is used as a pharmaceutical agent for its androgenic, estrogenic, and progestational activities. It is particularly useful in the treatment of conditions related to hormonal imbalances, such as androgen deficiency, menopause, and osteoporosis. Its multifaceted hormonal profile allows for a versatile approach to managing various health issues.
Used in Sports Performance Enhancement:
As an anabolic steroid, 19-Norandrostenediol is used by athletes and bodybuilders to enhance sports performance. Its androgenic properties promote muscle growth and strength, while its estrogenic and progestational activities may help in reducing muscle fatigue and improving recovery times. However, it is essential to note that the use of anabolic steroids for performance enhancement is controversial and may be prohibited in professional sports due to potential health risks and ethical concerns.
Used in Research and Development:
19-Norandrostenediol serves as a valuable compound in scientific research, particularly in the fields of endocrinology, pharmacology, and sports medicine. Its unique hormonal activities make it an interesting subject for studying the effects of anabolic steroids on the human body and developing new treatments for various medical conditions.
Originator
19-Norandrostenediol,Epochem Co., Ltd.
Manufacturing Process
To a suspension of 6 parts of lithium aluminum hydride in 2100 parts of ether
there are added, with stirring, 7.2 parts of 19-nortestosterone in 700 parts of
ether. The mixture is stirred with heating on the steam bath for 45 min, after
which the unreacted lithium aluminum hydride is decomposed by addition of
acetone. The mixture is diluted with water and the organic layer is separated
and washed with water and saturated aqueous sodium chloride solution. After
drying over anhydrous sodium sulfate, the ether solution is evaporated under
vacuum and the residue is dissolved in benzene and thus applied to a
chromatography column containing 760 parts of silica gel. The column is
developed with benzene and then with 5 and 10% solutions of ethyl acetate in
benzene. Further elution with a 15% solution of ethyl acetate in benzene and
concentration of the eluate yields a residue which is recrystallized from
acetone and water, ethyl acetate and petroleum ether, and again from acetone
and water to yield the 4-estrene-3β,17β-diol, melting point 169°-172°C.
Therapeutic Function
Anabolic
Check Digit Verification of cas no
The CAS Registry Mumber 19793-20-5 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,9,7,9 and 3 respectively; the second part has 2 digits, 2 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 19793-20:
(7*1)+(6*9)+(5*7)+(4*9)+(3*3)+(2*2)+(1*0)=145
145 % 10 = 5
So 19793-20-5 is a valid CAS Registry Number.
InChI:InChI=1/C18H28O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h10,12-17,19-20H,2-9H2,1H3/t12-,13?,14?,15?,16?,17-,18-/m0/s1
19793-20-5Relevant articles and documents
An easy stereoselective synthesis of 5(10)-estrene-3β,17α-diol, a biological marker of pregnancy in the mare
Balssa, Frédéric,Fischer, Michael,Bonnaire, Yves
, p. 1 - 4 (2014/06/09)
5(10)-Estrene-3β,17α-diol is an essential reference material for doping analysis in horse-racing laboratories. It is used to detect misuse, for doping purpose, of the pregnancy status in the mare. Its stereoselective synthesis from 17β-estradiol-3-methyl ether (prepared from estrone or 17β-estradiol) was performed in four steps: (1) Mitsunobu inversion of the 17β-alcohol; (2) Birch reduction of the aromatic ring; (3) stereoselective reduction of the 3-ketone via Noyori asymmetric transfer hydrogenation; (4) chemoenzymatic purification.
Neurosteroid analogues. 4. The effect of methyl substitution at the C-5 and C-10 positions of neurosteroids on electrophysiological activity at GABA(A) receptors
Han, Mingcheng,Zorumski, Charles F.,Covey, Douglas F.
, p. 4218 - 4232 (2007/10/03)
A series of analogues of the neuroactive steroids 3α-hydroxy-5α- pregnan-20-one and 3α-hydroxy-5β-pregnan-20-one were studied to elucidate the mode of binding of 5α- and 5β-reduced steroids to steroid binding sites on GABA(A) receptors. Analogues which were either 3α-hydroxy-20-ketosteroids or 3α-hydroxysteroid-17β-carbonitriles and which contained various methyl group substitution patterns at C-5 and C-10 were prepared. Evaluations utilized whole-cell patch clamp electrophysiological methods carried out on cultured rat hippocampal neurons, and the results obtained with the rigid 17β-carbonitrile analogs were analyzed using molecular modeling methods. The molecular modeling results provide a rationale for the observation that the configuration of the hydroxyl group at C-3 is a greater determinant of anesthetic potency than the configuration of the A,B ring fusion at C-5. The electrophysiological results identify steric restrictions for the space that can be occupied in 5α- and 5β-reduced steriod modulators of GABA(A) recepters in the regions of space proximate to the steroid C-5, C-10, and possibly C-4 positions. This information is useful for the development of nonsteroidal analogues that can modulate GABA(A) receptors via interactions at steroid binding sites.
Facial selectivity in the hydroboration of androst-4-enes
Hanson, James R.,Hitchcock, Peter B.,Liman, Mansur D.,Naragatnam, Sivajini
, p. 2183 - 2188 (2007/10/02)
In the absence of an allylic hydroxy group, the stereochemistry of hydroboration of an androst-4-ene is determined by the presence and stereochemistry of the C-10 methyl group.Allylic hydroxy groups at C-3 direct the hydroboration/oxidation to the anti-face.In the case of the 3α-alcohol, this effect is in opposition to the normal hydration from the α-face of the steroid and leads to the 4β-alcohol.The stereochemistry of 4β,17β-diacetoxy-19-nor-5β-androstane was established by X-ray crystallography.
