19-norandrostenedione

Synonyms :
4-estrene-3,17-dione, delta4-Estrene-3,17-dione, NOR

Status : experimental

Category

Steroids

Description

19-Norandrostenedione refers to two steroid isomers that were once marketed as dietary supplements and mainly used by body builders. After 2005, 19-Norandrostenedione was regulated in the United States as a schedule III controlled substance, as well as banned from use in competitive sports by the World Anti-Doping Agency. In the body 19-norandrostenedione is rapidly metabolized into nandrolone, also known as nortestosterone.

Used

The claim that supplemental 19-norandrostenedione has anabolic effects is unsubstantiated.

Mechanism Of Action

19-Norandrostenedione may be metabolized to 19-nortestosterone in both men and women. 19-Norandrostenedione, also known as nandrolone, is the basic substance of some very popular injectable anabolic steroids, however 19-norandrostenedione is not metabolized to testosterone. Whether or not increases in 19-nortestosterone levels would be sustained long enough by taking 19-norandrostenedione to show an increase in nitrogen retention and muscle strength and mass is unknown. 19-Norandrostenedione has also been shown to bind to androgen receptors with high selectivity. Transactivation of androgen receptor dependent reporter gene expression was 10 times lower than that produced by dihydrotestosterone. [1]

Metabolism

Specific metabolites of 19-nor-5-androstene-3, 17-dione are 19-nordehydroandrosterone and 19-nordehydroepiandrosterone.

Absorption

Absorption appears variable, but some absorption does occur.

Chemical Classification

This compound belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane.

Estrogens and derivatives

Organic compounds

Lipids and lipid-like molecules

Steroids and steroid derivatives

Estrane steroids

Chemical Name

4-estrene-3,17-dione

Calculated Property

kind Value Source
logP 2.53 ALOGPS
logS -3.8 ALOGPS
Water Solubility 4.54e-02 g/l ALOGPS
logP 3.63 ChemAxon
IUPAC Name (1S,2R,10R,11S,15S)-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-ene-5,14-dione ChemAxon
Traditional IUPAC Name 19-norandrostenedione ChemAxon
Molecular Weight 272.382 ChemAxon
Monoisotopic Weight 272.177630012 ChemAxon
SMILES [H][C@@]12CCC(=O)[C@@]1(C)CC[C@]1([H])[C@@]3([H])CCC(=O)C=C3CC[C@@]21[H] ChemAxon
Molecular Formula C18H24O2 ChemAxon
InChI InChI=1S/C18H24O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h10,13-16H,2-9H2,1H3/t13-,14+,15+,16-,18-/m0/s1 ChemAxon
InChIKey InChIKey=JRIZOGLBRPZBLQ-QXUSFIETSA-N ChemAxon
Polar Surface Area (PSA) 34.14 ChemAxon
Refractivity 79.13 ChemAxon
Polarizability 31.54 ChemAxon
Rotatable Bond Count 0 ChemAxon
H Bond Acceptor Count 2 ChemAxon
H Bond Donor Count 0 ChemAxon
pKa (strongest acidic) 19.19 ChemAxon
pKa (strongest basic) -4.7 ChemAxon
Physiological Charge 0 ChemAxon
Number of Rings 4 ChemAxon
Bioavailability 1 ChemAxon
Rule of Five 1 ChemAxon
Ghose Filter 1 ChemAxon
MDDR-Like Rule 0 ChemAxon

Affected organism

Humans and other mammals