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M7252

Sigma-Aldrich

17α-Methyltestosterone

solid (photosensitive)

Synonym(s):

17α-Methyl-4-androsten-17β-ol-3-one, 17β-Hydroxy-17α-methyl-4-androsten-3-one, Mesterone, Methyltestosterone

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About This Item

Empirical Formula (Hill Notation):
C20H30O2
CAS Number:
58-18-4
Molecular Weight:
302.45
Beilstein:
2057425
EC Number:
200-366-3
MDL number:
MFCD00003655
UNSPSC Code:
51111800
PubChem Substance ID:
24897147

biological source

synthetic (organic)

Quality Level

100

sterility

non-sterile

Assay

≥98% (HPLC)

form

solid (photosensitive)

drug control

USDEA Schedule III; Home Office Schedule 4.2; regulated under CDSA - not available from Sigma-Aldrich Canada

color

white

mp

162-168 °C (lit.)

solubility

H2O: ≤0.5 mg/mL
ethanol: 22 mg/mL
45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: 4.8 mg/mL

shipped in

ambient

storage temp.

room temp

SMILES string

C[C@]1(O)CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C

InChI

1S/C20H30O2/c1-18-9-6-14(21)12-13(18)4-5-15-16(18)7-10-19(2)17(15)8-11-20(19,3)22/h12,15-17,22H,4-11H2,1-3H3/t15-,16+,17+,18+,19+,20+/m1/s1

InChI key

GCKMFJBGXUYNAG-HLXURNFRSA-N

Gene Information

human ... AR(367)
rat ... Ar(24208)

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Biochem/physiol Actions

Methyltestosterone (Mesterone) is an androgen and anabolic steroid.

Pictograms

Health hazard
GHS08

Signal Word

Danger

Hazard Statements

H350 - H361fd

Hazard Classifications

Carc. 1B - Repr. 2

Storage Class Code

6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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S Herfeld et al.
Hormones and behavior, 34(3), 303-319 (1999-01-08)
Adult males of African weakly discharging electric fish (family: Mormyridae) are distinguished from juveniles and adult females by a dorsally directed indentation of the posterior ventral body wall and by massive bone expansion of the bases of a select number
Daniela Stange et al.
Ecotoxicology and environmental safety, 75(1), 94-101 (2011-09-29)
Molluscs are raising attention as ecotoxicological test organisms due to their high diversity and ecological importance. The ovoviviparous prosobranch gastropod Potamopyrgus antipodarum (freshwater mudsnail) responds very sensitively to xenobiotics and has therefore been proposed as OECD standard test organism. Endocrine
C Gómez et al.
Steroids, 78(1), 44-52 (2012-11-07)
Methyltestosterone (MT) is one of the most frequently detected anabolic androgenic steroids in doping control analysis. MT misuse is commonly detected by the identification of its two main metabolites excreted as glucuronide conjugates, 17α-methyl-5α-androstan-3α,17β-diol and 17α-methyl-5β-androstan-3α,17β-diol. The detection of these
Yuqian Han et al.
Food chemistry, 135(4), 2988-2993 (2012-09-18)
A simple, rapid and sensitive method was developed for determination of 17α-methyltestosterone in aquatic products by extraction with subcritical 1,1,1,2-tetrafluoroethane (R134a) extraction and high performance liquid chromatography (HPLC). Response surface methodology (RSM) was adopted to optimise extraction pressure, temperature and
Carlos A A Penatti et al.
Neuropharmacology, 61(4), 653-664 (2011-06-08)
Disruption of reproductive function is a hallmark of abuse of anabolic androgenic steroids (AAS) in female subjects. To understand the central actions of AAS, patch clamp recordings were made in estrous, diestrous and AAS-treated mice from gonadotropin releasing hormone (GnRH)
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