Methyltrienolone
Synonym(s):(17b)-17-Hydroxy-17-methyl-Estra-4,9,11-trien-3-one;Methyltrienolone;Metribolone;NSC 92858;RU 1881
- CAS NO.:965-93-5
- Empirical Formula: C19H24O2
- Molecular Weight: 284.39
- MDL number: MFCD00199021
- EINECS: 663-842-3
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-05-14 16:41:43
What is Methyltrienolone?
Description
Methyltrienolone is an orally active anabolic-androgen steroid being a 17α-alkylated nandrolone (19-nortestosterone) derivative. It is not sold as a prescription drug and 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 in prostatic tumors.
Chemical properties
Pale Yellow Solid
The Uses of Methyltrienolone
An anabolic steroid.
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
Properties of Methyltrienolone
Melting point: | 170° |
Boiling point: | 485.9±45.0 °C(Predicted) |
alpha | D20 -58.7° (c = 0.5 in ethanol) |
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 |
CAS DataBase Reference | 965-93-5(CAS DataBase Reference) |
Safety information for Methyltrienolone
Signal word | Warning |
Pictogram(s) |
Exclamation Mark Irritant GHS07 |
GHS Hazard Statements |
H319:Serious eye damage/eye irritation |
Precautionary Statement Codes |
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. |
Computed Descriptors for Methyltrienolone
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| |
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