Methyltrienolone Chemical Properties

Melting point:

170°

alpha 

D20 -58.7° (c = 0.5 in ethanol)

Boiling point:

485.9±45.0 °C(Predicted)

Density 

1.17±0.1 g/cm3(Predicted)

storage temp. 

2-8°C

solubility 

DMSO: ≥10mg/mL

form 

powder

pka

14.79±0.40(Predicted)

color 

light yellow to yellow

optical activity

[α]/D -48 to -68°

InChI

InChI=1/C19H24O2/c1-18-9-7-15-14-6-4-13(20)11-12(14)3-5-16(15)17(18)8-10-19(18,2)21/h7,9,11,16-17,21H,3-6,8,10H2,1-2H3/t16-,17+,18+,19+/s3

InChIKey

CCCIJQPRIXGQOE-XWSJACJDSA-N

SMILES

[C@@]12([H])CC[C@@](O)(C)[C@@]1(C)C=CC1=C3CCC(=O)C=C3CC[C@@]21[H] |&1:0,4,7,21,r|

CAS DataBase Reference

965-93-5(CAS DataBase Reference)

Safety Information

WGK Germany 

3

DEA Controlled Substances

CSCN: 4000
CSA SCH: Schedule III
NARC: No

Methyltrienolone Usage And Synthesis

Description

Methyltrienolone, also called metribolone, is an orally active anabolic-androgen steroid being a 17α-alkylated nandrolone (19-nortestosterone) derivative. It is not sold as a prescription drug or a dietary supplement due to its strong androgenic side effects and liver toxicity. However, it is often used as the reference point for in vitro biological activity for biochemical studies. It can bind strongly to the androgen receptor and can be used as an affinity label of the androgen receptor in the prostate and prostatic tumors.

Chemical Properties

Pale Yellow Solid

Uses

Methyltrienolone is a synthetic derivative of testosterone that is used in the medical field as an androgen and anabolic agent. It has been used to treat breast cancer, prostate cancer, and other cancers that are sensitive to hormones.

Definition

ChEBI: Methyltrienolone, also known as 7beta-hydroxy-17-methylestra-4,9,11-trien-3-one, is a synthetic non-aromatisable androgen and anabolic steroid. It binds strongly to the androgen receptor and has therefore also been used as an affinity label for this receptor in the prostate and in prostatic tumors. It has a role as an androgen. It is an anabolic androgenic steroid, a 17beta-hydroxy steroid and a 3-oxo steroid. It derives from a hydride of an estrane.

Biochem/physiol Actions

Androgen receptors (ARs) are nuclear hormone receptors/transcription factors. R1881, also known as methyltrienolone, is a synthetic androgen. It is the gold standard AR agonist.

References

https://en.wikipedia.org/wiki/Metribolone
https://www.drugbank.ca/drugs/DB02998
https://pubchem.ncbi.nlm.nih.gov/compound/Methyltrienolone
Kazlauskas R. (2010) Designer Steroids. In: Thieme D., Hemmersbach P. (eds) Doping in Sports: Biochemical Principles, Effects and Analysis. Handbook of Experimental Pharmacology, vol 195. Springer, Berlin, Heidelberg

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