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Mestanolone structure
Mestanolone structure

Mestanolone

Iupac Name:(5S,8R,9S,10S,13S,14S,17S)-17-hydroxy-10,13,17-trimethyl-2,4,5,6,7,8,9,11,12,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-3-one
CAS No.: 521-11-9
Molecular Weight:304.46688
Modify Date.: 2022-11-02 11:25
Introduction: Mestanolone is an orally active anabolic-androgenic steroid and the 17α-methylated derivative of dihydrotestosterone (DHT), which is an endogenous androgen sex steroid and hormone. It is capable of increasing testosterone benefit, suppressing estrogen effect, leaning muscle tissue, increasing strength as well as improving drive and focus. It is mainly used for the treatment of male hypogonadism and decreased sperm infertility. View more+
1. Names and Identifiers
1.1 Name
Mestanolone
1.2 Synonyms

(5a,17b)-17-Hydroxy-17-methylandrostan-3-one (5S,8R,9S,10S,13S,14S,17S)-17-Hydroxy-10,13,17-trimethylhexadecahydro-3H-cyclopenta[a]phenanthren-3-one (5α,17Β)-17-Hydroxy-17-methylandrostan-3-one 17ALPHA-METHYLDIHYDROTESTOSTERONE 17a-Methylandrostan-17b-ol-3-one 17a-Methylandrostan-3-on-17b-ol 17a-Methylandrostanolone 17b-Hydroxy-17-methyl-5a-androstan-3-one 17α-Methyl-17Β-hydroxy-5α-androstan-3-one 17α-Methylandrostan-17Β-ol-3-one 17α-Methyldihydrotestosterone 17Β-Hydroxy-17-methyl-5α-androstan-3-one 17Β-Hydroxy-17α-methyl-5α-androstan-3-one 3-KETO-17B-HYDROXY-17A-METHYL-5A-ANDROSTANE 5-ALPHA-ANDROSTAN-17-ALPHA-METHYL-17-BETA-OL-3-ONE 5ALPHA-ANDROSTANE-17ALPHA-METHYL-17BETA-OL-3-ONE 5α-Androstan-3-one, 17Β-hydroxy-17-methyl- Anabo Andoron Androstan-3-one, 17-hydroxy-17-methyl-, (5α,17Β)- Antalone Assimil Duramin EINECS 208-302-6 MESTALINE Mestanolone (JAN) Methybol METHYLANDROSTANOLONE METHYLDIHYDROTESTOSTERONE MFCD00021158 Preroide Prohormo Tantaron

1.3 CAS No.
521-11-9
1.4 CID
10633
1.5 EINECS(EC#)
208-302-6
1.6 Molecular Formula
C20H32O2 (isomer)
1.7 Inchi
InChI=1S/C20H32O2/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/h13,15-17,22H,4-12H2,1-3H3/t13-,15+,16-,17-,18-,19-,20-/m0/s1
1.8 InChkey
WYZDXEKUWRCKOB-YDSAWKJFSA-N
1.9 Canonical Smiles
CC12CCC(=O)CC1CCC3C2CCC4(C3CCC4(C)O)C
1.10 Isomers Smiles
C[C@]12CCC(=O)C[C@@H]1CC[C@@H]3[C@@H]2CC[C@]4([C@H]3CC[C@]4(C)O)C
2. Properties
2.1 Density
1.064
2.1 Melting point
189 - 196 C
2.1 Boiling point
416.1°Cat760mmHg
2.1 Refractive index
1.528
2.1 Flash Point
177.6°C
2.1 Precise Quality
304.24000
2.1 PSA
37.30000
2.1 logP
4.34920
2.1 Appearance
white to off-white crystalline powder
2.2 Chemical Properties
White Solid
2.3 pKa
15.15±0.60(Predicted)
2.4 Water Solubility
practically insoluble < RESIDUES 0.25% max
2.5 Stability
Stable at normal temperatures and pressures.
2.6 StorageTemp
Controlled Substance, -20?C Freezer
3. Use and Manufacturing
3.1 Purification Methods
Dissolve mestanolone in Et2O, wash it with N NaOH, H2O, dry it (Na2SO4), evaporate and recrystallise it from EtOAc. The semicarbazone has m 235-236o (from EtOH). [Ruzicka et al. Helv Chim Acta 18 1487 1935.]
3.2 Usage
Anabolic steroid. Controlled substance.
4. Safety and Handling
4.1 Symbol
GHS08
4.1 Hazard Codes
Xn
4.1 Signal Word
Warning
4.1 Risk Statements
R40
4.1 Safety Statements
S22;S36
4.1 Hazard Declaration
H351
4.1 RIDADR
HAZARD
4.1 Caution Statement
P281
4.1 WGK Germany
3
4.1 RTECS
BV8064500
4.1 Safety
Hazard Codes:Xn
Risk Statements:40
40:Limited evidence of a carcinogenic effect
Safety Statements:22-36
22:Do not breathe dust
36:Wear suitable protective clothing
WGK Germany:3
4.2 Specification

?The Mestanolone with the cas number 521-11-9, is also called (1) 17-alpha-Methyldihydrotestosterone ; (2) 17alpha-Methyl-5alpha-dihydrotestosterone ; (3) 17alpha-Methylandrostan-17beta-ol-3-one ; (4) 17alpha-Methylandrostanolone ; (5) 17alpha-Methyldihydrotestosterone ; (6) 17alpha-methyl-5alpha-androstan-17beta-ol-3-one ; (7) 17alpha-methylandrostan-3-on-17beta-ol ; (8) 17beta-Hydroxy-17alpha-methyl-5alpha-androstan-3-one ; (9) 5-alpha-Androstane-17-alpha-methyl-17-beta-ol-3-one ; (10) 5alpha-Androstane-17alpha-methyl-17beta-ol-3-one ; (11) Andoron ; (12) Androstalone ; (13) Assimil ; (14) Ermalone (VAN) ; (15) Mestanolona ; (16) Mestanolone ; (17) Mestanolonum ; (18) Methybol ; (19) Methylantalon ; (20) Methyldihydrotestosterone ; (21) Preroide ; (22) Tantarone . It belongs to the following product Categories: (1)Steroids; (2)Biochemistry; (3)Hydroxyketosteroids?

Propertes of Mestanolone: (1)ACD/LogP: 4.29 ; (2)# of Rule of 5 Violations: 0 ; (3)ACD/LogD (pH 5.5): 4.29 ; (4)ACD/LogD (pH 7.4): 4.29 ; (5)ACD/BCF (pH 5.5): 1076.26 ; (6)ACD/BCF (pH 7.4): 1076.26 ; (7)ACD/KOC (pH 5.5): 5150.44 ; (8)ACD/KOC (pH 7.4): 5150.44 ; (9)#H bond acceptors: 2 ; (10)#H bond donors: 1 ; (11)#Freely Rotating Bonds: 1 ; (12)Polar Surface Area: 26.3??2 ; (13)Index of Refraction: 1.528 ; (14) Molar Refractivity: 88.1 cm3 ; (15)Molar Volume: 286 cm3 ; (16)Polarizability: 34.92 ×10-24cm3 ; (17)Surface Tension: 39.2 dyne/cm ; (18)Density: 1.064 g/cm3 ; (19)Flash Point: 177.6 °C ; (20)Enthalpy of Vaporization: 77.31 kJ/mol ; (21)Boiling Point: 416.1 °C at 760 mmHg ; (22)Vapour Pressure: 1.16E-08 mmHg at 25°C

The Mestanolone is an orally bioavailable androgenic steroid that is highly androgenic while only slightly anabolic. It is incapable of aromatization and is not an agonist of the progesterone receptor. Dosages range from 10mg to 30mg a day for males. Women should avoid Mestanolone for it is very androgenic. Long term use, more than 12 weeks should be avoided do to hepatoxicity. Since Mestanolone is unable to convert to estrogen, it is very useful during cutting phase's or when one wishes to avoid excess weight gain.

You can still convert the following datas into molecular structure :
1. SMILES: O=C2C[C@@H]1CC[C@@H]3[C@@H]([C@@]1(C)CC2)CC[C@]4([C@H]3CC[C@@]4(O)C)C
2. InChI: InChI=1/C20H32O2/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/h13,15-17,22H,4-12H2,1-3H3/t13-,15+,16-,17-,18-,19-,20-/m0/s1

The Mestanolone toxic data can be showed in the following sheet.

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 1240mg/kg (1240mg/kg) ? Drugs in Japan Vol. 6, Pg. 817, 1982.
mouse LD50 oral > 3gm/kg (3000mg/kg) ? Drugs in Japan Vol. 6, Pg. 817, 1982.
mouse LD50 subcutaneous > 5gm/kg (5000mg/kg) ? Drugs in Japan Vol. 6, Pg. 817, 1982.
rat LD50 intraperitoneal > 2gm/kg (2000mg/kg) ? Drugs in Japan Vol. 6, Pg. 817, 1982.
rat LD50 oral > 3gm/kg (3000mg/kg) ? Drugs in Japan Vol. 6, Pg. 817, 1982.
rat LD50 subcutaneous > 5gm/kg (5000mg/kg) ? Drugs in Japan Vol. 6, Pg. 817, 1982.

4.3 Toxicity

CHEMICAL IDENTIFICATION

RTECS NUMBER :
BV8064500
CHEMICAL NAME :
5-alpha-Androstan-3-one, 17-beta-hydroxy-17-methyl-
CAS REGISTRY NUMBER :
521-11-9
BEILSTEIN REFERENCE NO. :
3207223
LAST UPDATED :
199612
DATA ITEMS CITED :
7
MOLECULAR FORMULA :
C20-H32-O2
MOLECULAR WEIGHT :
304.52
WISWESSER LINE NOTATION :
L E5 B666 OVTJ A1 E1 FQ F1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
>3 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: 6,817,1982
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
>2 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: 6,817,1982
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
>5 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: 6,817,1982
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
>3 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: 6,817,1982
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
1240 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: 6,817,1982
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
>5 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: 6,817,1982 ** REPRODUCTIVE DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
160 mg/kg
SEX/DURATION :
female 14-21 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - urogenital system
REFERENCE :
ENDOAO Endocrinology (Baltimore). (Williams & Wilkins Co., 428 E. Preston St., Baltimore, MD 21203) V.1- 1917- Volume(issue)/page/year: 94,979,1974
5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Carcinogenicity, Category 2

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word

Warning

Hazard statement(s)

H351 Suspected of causing cancer

Precautionary statement(s)
Prevention

P201 Obtain special instructions before use.

P202 Do not handle until all safety precautions have been read and understood.

P280 Wear protective gloves/protective clothing/eye protection/face protection.

Response

P308+P313 IF exposed or concerned: Get medical advice/ attention.

Storage

P405 Store locked up.

Disposal

P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

8. Precursor and Product
9. Computational chemical data
  • Molecular Weight: 304.46688g/mol
  • Molecular Formula: C20H32O2
  • Compound Is Canonicalized: True
  • XLogP3-AA: null
  • Exact Mass: 304.240230259
  • Monoisotopic Mass: 304.240230259
  • Complexity: 500
  • Rotatable Bond Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 2
  • Topological Polar Surface Area: 37.3
  • Heavy Atom Count: 22
  • Defined Atom Stereocenter Count: 7
  • Undefined Atom Stereocenter Count: 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Isotope Atom Count: 0
  • Covalently-Bonded Unit Count: 1
  • CACTVS Substructure Key Fingerprint: AAADcfB4MAAAAAAAAAAAAAAAAAAAAYAAAAAwYMAAAAAAAGDAAAAAGgAACAAAD0SAgAACAAAAAgAIAIAQAAAAAAAAAAAAAAEAAAAAABIAAAAAQAAEAAAAAAGIyPCPgAAAAAAAAACAAAQAACAAAYAADAAAAA==
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