Methyltestosterone

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Cat Number

API0232273

CAS Number

58-18-4

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CAS Number

58-18-4

EINECS

200-366-3

Storage

Store at room temperature

Synonyms

17-Methyltestosterone; Metandren; Testred; Android; 17alpha-Methyltestosterone; Androsten; Dumogran; Malestrone

Molecular Formula

C20H30O2

Molecular Weight

302.5

Smiles

C[C@]12CCC(=O)C=C1CC[C@@H]3[C@@H]2CC[C@]4([C@H]3CC[C@]4(C)O)C

Appearance

White to creamy-white powder

Melting Point

162-168°C (lit.)

Boiling Point

422.7±45.0°C (Predicted)

Relative Density

1.082

General Description

Methyltestosterone is a synthetic androgenic steroid with a 17α-methyl group, allowing oral activity. Its chemical structure is 17α-methyl-17β-hydroxy-4-androsten-3-one. Methyltestosterone is a white to off-white crystalline powder, practically insoluble in water but soluble in organic solvents. It is a potent androgen with both anabolic and androgenic effects.

Mechanism of Action

Methyltestosterone binds to the androgen receptor in target tissues, promoting protein synthesis, muscle growth, and the development of male secondary sex characteristics. It also suppresses gonadotropin secretion through negative feedback, reducing testosterone production. The drug has a significant androgenic effect, which is responsible for its virilizing side effects.

Application

Methyltestosterone is indicated for the treatment of male hypogonadism, delayed puberty, and for the palliation of certain breast cancers in women. It is also used for the treatment of osteoporosis and for the management of the symptoms of androgen deficiency. The drug is associated with hepatotoxicity and is no longer widely used.

In zebrafish, 17α‑methyltestosterone (MT) induced gonadal masculinization and accelerated spermatogenesis, upregulating male differentiation genes (amh, dmrt1, gsdf) and androgen synthesis genes, while repressing ovarian genes. Histone modifications were altered. Contrary to expectations, cyp19a1a and foxl2 expression differences were not significant early. Both androgen production and aromatase inhibition contribute to MT‑induced masculinization and natural testicular differentiation.

Fig. 1 General overview schematic of the zebrafish gonad RNA-Seq experiment. (Lee SLJ, et al., 2017)

References

Lee SLJ, et al. Histological and transcriptomic effects of 17α-methyltestosterone on zebrafish gonad development. BMC Genomics. 2017;18(1):557.

Using a semi-targeted approach with synthetic reference compounds, two diastereomeric long-term metabolites with rearranged D-ring and fully reduced A-ring were identified in urine after methyltestosterone administration; only the 5β-metabolite was detected after metandienone. Additionally, 3α,5β-tetrahydro-epi-methyltestosterone was identified in both administrations. These findings provide new insights into the metabolism of 17α-methyl steroids and have applicability for anti-doping analysis.

Fig. 2 Proposed metabolism of methyltestosterone and metandienone. (Loke S, et al., 2021)

References

Loke S, et al. New Insights into the Metabolism of Methyltestosterone and Metandienone: Detection of Novel A-Ring Reduced Metabolites. Molecules. 2021;26(5):1354.

Does Methyltestosterone require protection from light during long-term storage?

Yes, it is photosensitive. UV exposure can cause photodegradation and discoloration of the steroid ring. Store in light-resistant containers, preferably amber glass.

What is the recommended storage temperature for Methyltestosterone?

Store at controlled room temperature (15-25°C). Avoid excessive heat above 30°C, which can soften the powder and accelerate oxidation.

Is Methyltestosterone stable in tablet and capsule formulations?

Yes, when formulated with standard excipients and protected from moisture.

How is the impurity testosterone (a process-related impurity) monitored?

This impurity is quantified using a stability-indicating HPLC method, ensuring it remains within pharmacopoeial limits.