science

Mibolerone

Mibolerone is a science topic covered in the lgStudy science library. This page brings together a partial reference excerpt, illustrations, worked examples, real-world applications and a short study plan, so you can understand Mibolerone rather than just read about it. In short: Mibolerone, also known as dimethylnortestosterone (DMNT) and sold under the brand names Cheque Drops and Matenon, is a synthetic, orally active, and extremely potent anabolic–androgenic steroid (AAS) and a 17α-alkylated nandrolone (19-nortestosterone) derivative which was marketed by Upjohn for use as a veterinary drug. It was indicated specifically as an oral treatment for prevention of estrus (heat) in adult femal…

Key takeaways

Mibolerone belongs to science; place it in that map before memorising details.
Learn the definition first, then one example that makes the definition concrete.
Connect Mibolerone to a quantity you can measure, compute or draw — that is where exam questions come from.
Reproduce the core statement of Mibolerone from memory before moving on to harder problems.

Reference excerpt

Mibolerone, also known as dimethylnortestosterone (DMNT) and sold under the brand names Cheque Drops and Matenon, is a synthetic, orally active, and extremely potent anabolic–androgenic steroid (AAS) and a 17α-alkylated nandrolone (19-nortestosterone) derivative which was marketed by Upjohn for use as a veterinary drug. It was indicated specifically as an oral treatment for prevention of estrus (heat) in adult female dogs.

Side effects

Pharmacology

Pharmacodynamics Mibolerone has both higher affinity and greater selectivity for the androgen receptor (AR) than does the related potent AAS metribolone (17α-methyl-19-nor-δ9,11-testosterone), although potent and significant progestogenic activity remains present. However, another study found that mibolerone and metribolone had similar affinity for the progesterone receptor (PR) but that mibolerone only had around half the affinity of metribolone for the AR.

Chemistry

Mibolerone, also known as 7α,17α-dimethyl-19-nortestosterone (DMNT) or as 7α,17α-dimethylestr-4-en-17β-ol-3-one, is a synthetic estrane steroid and a 17α-alkylated derivative of nandrolone (19-nortestosterone). It is the 17α-methyl derivative of trestolone (7α-methyl-19-nortestosterone; MENT). Other related AAS include metribolone (17α-methyl-δ9,11-19-nortestosterone) and dimethyltrienolone (7α,17α-dimethyl-δ9,11-19-nortestosterone).

Synthesis The original patented synthesis was revised: Precursor (also needed for Plomestane):

The reaction of Bolandione [734-32-7] (1) with triethyl orthoformate gave 3-Ethoxyestra-3,5-dien-17-one [2863-88-9] (2) in 64% yield. Organometallic reaction with methyl lithium followed by hydrolysis of the dienol ether gave Normethandrone [514-61-4] (5) in 40% yield. In an alternative synthesis, reaction of Estr-5(10)-ene-3,17-dione [3962-66-1] (3) with methanol catalyzed by malonic acid gave a near quantitivate yield of the ketal, 3,3-dimethoxyestr-5(10)-en-17-one [19257-34-2] (4). Reaction with the organometallic reagent and hydrolysis in this case afforded a much higher yield of product (86.7%) than in the first case. Oxidation with chloranil afforded a 75.6% yield of 17-methyl-6-dehydronandrolone (6). Conjugate addition of methyl lithium in the presence of cuprous iodide (c.f. Gillman reagent) gave a 72.5% yield of mibolerone (7).

In the other synthesis heating nandrolone acetate [1425-10-1] (1) with chloranil gives 6-Dehydronandrolone Acetate [2590-41-2] (2), and reaction of that compound with methylmagnesium bromide in the presence of cuprous chloride gives (after saponification), Trestolone (7alpha-Methylnandrolone) [3764-87-2] (3). The alcohol at C17 is then oxidized to a ketone, Mentabolan [17000-78-1] (4). Enamines are commonly used to activate adjacent functions; they are also not infrequently used, as in this case, as protecting groups. Thus, reaction of the intermediate with pyrrolidine gives dienamine PC135056261 (5). This transformation emphasizes the clear difference in reactivity between ketones at C7 and C17. A second methyl Grignard addition gives the corresponding 17α-methyl derivative. Hydrolysis of the enamine function then affords mibolerone (6). For SAR purposes compare for bolasterone and calusterone.

History Mibolerone was first synthesized in 1963.

Society and culture

Generic names Mibolerone is the generic name of the drug and its INNTooltip International Nonproprietary Name, USANTooltip United States Adopted Name, and BANTooltip British Approved Name. It is also known as dimethylnortestosterone (DMNT) and by its former developmental code name U-10997.

Brand names Mibolerone has been marketed under the brand names Cheque Drops and Matenon.

References

External links Cheque Drops (mibolerone) - William Llewellyn's Anabolic.org Archived 2016-07-26 at the Wayback Machine

Illustrations

Worked examples

Example 1 — a first encounter with Mibolerone

Start with the simplest possible case. Write down what Mibolerone claims or describes in one sentence, then invent the smallest concrete situation in which that sentence is true. In science, the smallest case is usually a single object, a single equation or a single measurement. Check that every symbol or term in your sentence has a meaning in that case.

Example 2 — changing one variable

Take the situation from Example 1 and change exactly one quantity: double it, halve it, or set it to zero. Predict what should happen to Mibolerone before you calculate. Comparing your prediction with the result is the fastest way to find out whether you understand the idea or only the words.

Example 3 — an exam-style question

Typical questions about Mibolerone ask you to (a) state it precisely, (b) apply it to given data, and (c) explain a limitation. Practise writing all three answers in under five minutes; the third part is what separates a full-mark answer from an average one.

Applications of Mibolerone

In research: Mibolerone appears in science research whenever the underlying quantities have to be modelled precisely. Papers usually cite it as a starting assumption and then explore where it breaks down.
In technology and industry: Engineering practice reuses Mibolerone in design rules, simulations and safety margins. Knowing the idea lets you read a specification sheet and understand why the numbers look the way they do.
In the classroom: Mibolerone is common in secondary-school and first-year university syllabi. It links to neighbouring topics Abandoned drugs, Androgens, Drugs not assigned an ATC code, so understanding it makes those chapters shorter.
In everyday life: Look for Mibolerone outside the textbook — in sport, cooking, traffic, electronics or the sky above you. An example you found yourself is remembered far longer than one you were given.

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How to study Mibolerone in 20 minutes

Read the reference excerpt below once, without taking notes.
Close the page and write down what Mibolerone means in your own words.
Compare your version with the excerpt and mark what you missed.
Work through the three examples above with pen and paper.
Explain Mibolerone out loud to somebody else — or to Teacher Smith in the lgStudy chat.

Frequently asked questions

What is Mibolerone in simple terms?

Why does Mibolerone matter?

Because it connects several science ideas at once: it gives you a definition you can apply, a quantity you can calculate, and a way to check whether a result is plausible.

How should I study Mibolerone?

Read the excerpt, restate it from memory, then work through the examples and applications listed on this page. The five-step study plan above takes about twenty minutes.

What does this page cover?

It gives you a compact reference excerpt plus original lgStudy explanations, examples, applications and study material on Mibolerone.