Oxymetholone

Iupac Name：(2Z,5S,8R,9S,10S,13S,14S,17S)-17-hydroxy-2-(hydroxymethylidene)-10,13,17-trimethyl-1,4,5,6,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one

CAS No.: 434-07-1

Molecular Weight：332.484

Modify Date.: 2022-11-29 12:06

Introduction: Oxymetholone is a synthetic, orally active anabolic-androgenic steroid (AAS) and 17α-methylated derivative of dihydrotestosterone (DHT). It is mainly used for the treatment of osteroporosis and anemia (low red blood cell count). It can also stimulate the muscle growth in malnourished or underdeveloped patients. It also has the potential to treat the HIV wasting syndrome. Oxymetholone can also lead to an even buildup in strength, which is its secondary characteristics, making it an excellent steroid to be coupled with other anabolic steroids to yield synergetic effect. View more+

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1. Names and Identifiers

1.1 Name: Oxymetholone
1.2 Synonyms: (2Z,5S,8R,9S,10S,13S,14S,17S)-17-hydroxy-2-(hydroxyméthylidène)-10,13,17-triméthylhexadécahydro-3H-cyclopenta[a]phénanthrén-3-one (2Z,5S,8R,9S,10S,13S,14S,17S)-17-Hydroxy-2-(hydroxymethylene)-10,13,17-trimethylhexadecahydro-3H-cyclopenta[a]phenanthren-3-one (2Z,5S,8R,9S,10S,13S,14S,17S)-17-Hydroxy-2-(hydroxymethyliden)-10,13,17-trimethylhexadecahydro-3H-cyclopenta[a]phenanthren-3-on (2Z,5S,8R,9S,10S,13S,14S,17S)-17-hydroxy-2-(hydroxymethylidene)-10,13,17-trimethylhexadecahydro-3H-cyclopenta[a]phenanthren-3-one (2Z,5α,17Β)-17-Hydroxy-2-(hydroxymethylene)-17-methylandrostan-3-one (2Z,5α,17Β)-17-Hydroxy-2-(hydroxymethyliden)-17-methylandrostan-3-on (2Z,5α,17Β)-17-hydroxy-2-(hydroxymethylidene)-17-methylandrostan-3-one (5a,17b)-17-Hydroxy-2-(hydroxymethylene)-17-methylandrostan-3-one (5α,17β)-17-Hydroxy-2-(hydroxyMethylene)-17-Methylandrostan-3-one 17beta-Hydroxy-2-(hydroxymethylene)-17-methyl-5alpha-androstan-3-one Anasterone 17Β-Hydroxy-2-(hydroxymethylene)-17-methyl-5α-androstan-3-one 2-Hydroxymethylene-17a-methyl-17b-hydroxy-5a-androstan-3-one 2-Hydroxymethylene-17a-methylandrostan-17b-ol-3-one 4,5a-Dihydro-2-hydroxymethylene-17a-methyltestosterone 4,5-dihydro-2-hydroxymethylene-17-a-methyltestosterone 5ALPHA-ANDROSTAN-17ALPHA-METHYL-17BETA-OL-2-HYDROXYMETHYLENE-3-ONE 5-ALPHA-ANDROSTAN-2-HYDROXYMETHYLENE-17-ALPHA-METHYL-17-BETA-OL-3-ONE Adroidin Adroyd Anadrol Anadroyd ANASTERONE Androstan-3-one, 17-hydroxy-2-(hydroxymethylene)-17-methyl-, (2Z,5α,17Β)- Androstan-3-one, 17-hydroxy-2-(hydroxymethylene)-17-methyl-, (5α,17Β)- Becorel EINECS 207-098-6 MFCD00869395 Oximetholone OxyMetholone (Anadrol) Raboral Roboral Stanozolol impurity B

1.3 CAS No.: 434-07-1

1.4 CID: 5281034

1.5 EINECS(EC#): 207-098-6

1.6 Molecular Formula: C21H32O3 (isomer)

1.7 Inchi: InChI=1S/C21H32O3/c1-19-11-13(12-22)18(23)10-14(19)4-5-15-16(19)6-8-20(2)17(15)7-9-21(20,3)24/h12,14-17,22,24H,4-11H2,1-3H3/b13-12-/t14-,15+,16-,17-,19-,20-,21-/m0/s1

1.8 InChkey: ICMWWNHDUZJFDW-DHODBPELSA-N

1.9 Canonical Smiles: CC12CCC3C(C1CCC2(C)O)CCC4C3(CC(=CO)C(=O)C4)C

1.10 Isomers Smiles: C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@]2(C)O)CC[C@@H]4[C@@]3(C/C(=C/O)/C(=O)C4)C

2. Properties

2.1 Density: 1.169

2.1 Melting point: 172-180℃

2.1 Boiling point: 465.9°Cat760mmHg

2.1 Refractive index: 38 ° (C=1, CHCl3)

2.1 Flash Point: 249.7°C

2.1 Precise Quality: 332.23500

2.1 PSA: 57.53000

2.1 logP: 4.40100

2.1 Solubility: H2O: ≤0.5 mg/mL

2.2 AnalyticLaboratory Methods: ...UV spectral assay for oxymetholone; in bulk & tablet form; thin layer chromatographic analysis.

2.3 Appearance: white to light yellow solid

2.4 Carcinogenicity: Oxymetholone is reasonably anticipated to be a human carcinogenbased on limited evidence of carcinogenicity in humans.

2.5 Chemical Properties: Oxymetholone is a white to pale yellow crystallinesolid or powder. Odorless.

2.6 Color/Form: white to light yellow

2.7 Odor: ODORLESS

2.8 Physical: PHYSICAL DESCRIPTION: Odorless white to creamy white crystalline powder. (NTP, 1992)

2.9 pKa: 5.28±0.70(Predicted)

2.10 Water Solubility: H2O: ≤0.5?mg/mL

2.11 Spectral Properties: Specific optical rotation (sodium): +38 deg
Max absorption 285 nm (log epsilon= 3.99)

2.12 Stability: Stability May be light sensitive. Combustible. Incompatible with strong oxidizing agents.

2.13 StorageTemp: 2-8°C

3. Use and Manufacturing

3.1 Definition: ChEBI: A 3-oxo-steroid that is 4,5alpha-dihydrotestosterone which is substituted by a hydroxymethylidene group at position 2 and by a methyl group at the 17alpha position. A synthetic androgen, it was mainly used for the treatmen of anaemias until being replaced by treatments with fewer side effects.

3.2 General Description: Odorless white to creamy white crystalline powder.

3.3 GHS Classification: Signal: Warning
GHS Hazard Statements
Aggregated GHS information provided by 26 companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

H351 (92.31%): Suspected of causing cancer [Warning Carcinogenicity]
H361 (92.31%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

Precautionary Statement Codes
P201, P202, P281, P308+P313, P405, and P501

3.4 Methods of Manufacturing: <a class="pubchem-internal-link multiple-CIDs" href="https://pubchem.ncbi.nlm.nih.gov/compound/17alpha-methylandrostan-17beta-ol-3-one">17alpha-methylandrostan-17beta-ol-3-one</a> in anhydrous thiophene;-free benzene; is reacted with ethyl formate; & sodium hydride; by stirring mixture under nitrogen; ... several hr. Resulting sodium; derivative is washed & ... treated with cold dilute HCl to liberate crude oxymetholone; ... purified by recrystallization ...

3.5 Potential Exposure: Oxymetholone is a controlled substance(US), hormone and a systemic anabolic steroid.

3.6 Shipping: UN3077 Environmentally hazardous substances,solid, n.o.s., Hazard class: 9; Labels: 9-Miscellaneous hazardousmaterial, Technical Name Required.

3.7 Usage: Anabolic steroid. Controlled substance

3.8 Waste Disposal: It is inappropriate andpossibly dangerous to the environment to dispose ofexpired or waste pharmaceuticals by flushing them downthe toilet or discarding them to the trash. Householdquantities of expired or waste pharmaceuticals may bemixed with wet cat litter or coffee grounds, doublebaggedin plastic, discard in trash. Larger quantitiesshall carefully take into consideration applicable DEA,EPA, and FDA regulations. If possible return thepharmaceutical to the manufacturer for proper disposalbeing careful to properly label and securely package thematerial. Alternatively, the waste pharmaceutical shall belabeled, securely packaged and transported by a statelicensed medical waste contractor to dispose by burialin a licensed hazardous or toxic waste landfill orincinerator. Oxymetholone Preparation Products And Raw materials Raw materials

4. Safety and Handling

4.1 Symbol: GHS08

4.1 Hazard Codes: T

4.1 Signal Word: Warning

4.1 Risk Statements: R40

4.1 Safety Statements: 53-22-26-36/37/39-36

4.1 Exposure Standards and Regulations: Schedules of controlled substances are established by section 202 of the Controlled Substances Act (21 U.S.C. 812). Schedule III shall consist of the drugs and other substances, by whatever official name, common or usual name, chemical name, or brand name designated, listed in this section. Unless specifically excepted or unless listed in another schedule, any material, compound, mixture, or preparation containing any quantity of the following substances, including its salts, isomers, and salts of isomers whenever the existence of such salts of isomers is possible within the specific chemical designation. DEA Code #: 4000; Drug class: anabolic steroids.
The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl oxymetholone, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act.

4.2 Octanol/Water Partition Coefficient: log Kow 3.6 = (est)

4.3 Fire Hazard: Flash point data for Oxymetholone are not available. Oxymetholone is probably combustible.

4.4 Hazard Declaration: H351-H361

4.4 DisposalMethods: SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

4.5 RIDADR: NONH for all modes of transport

4.5 Safety Profile: Confirmed human carcinogen producing liver tumors. Human systemic effects by ingestion: impaired liver function. An experimental teratogen. Experimental reproductive effects. When heated to decomposition it emits acrid smoke and irritating fumes. See also TESTOSTERONE.

4.6 Caution Statement: P281

4.6 Formulations/Preparations: ... Available in USA as national formulary grade containing 97-103% active ingredient on dried basis with max 3% foreign steroids or other impurities. Tablets ... in 2.5, 5, 10 & 50 mg doses that contain 90-110% of stated amount oxymetholone... . In Japan ... available in powder form.

4.7 Incompatibilities: Incompatible with oxidizers (chlorates,nitrates, peroxides, permanganates, perchlorates, chlorine,bromine, fluorine, etc.); contact may cause fires or explosions.Keep away from alkaline materials, strong bases,strong acids, oxoacids, and epoxides. May be combustibleand light-sensitive.

4.8 WGK Germany: 3

4.8 RTECS: BV8060000

4.8 Safety: Confirmed human carcinogen producing liver tumors. Human systemic effects by ingestion: impaired liver function. An experimental teratogen. Experimental reproductive effects. When heated to decomposition it emits acrid smoke and irritating fumes. See also TESTOSTERONE.

4.9 Specification

The IUPAC name of?Oxymetholone is?(2Z,5S,8R,9S,10S,13S,14S,17S)-17-hydroxy-2-(hydroxymethylidene)-10,13,17-trimethyl-1,4,5,6,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one. With the?CAS registry number 434-07-1,?it is also named as 17-Hydroxy-5-alpha-androstan-3-one. The?product's categories are?pharmaceutical; biochemistry; hydroxyketosteroids; steroids. It is?odorless white crystalline powder?which is insoluble in water, easily soluble in chloroform, soluble in dioxane, vegetable oil, and slightly soluble in ethanol and?ether. Additionally, Oxymetholone may be light sensitive, combustible and?incompatible with strong oxidizing agents.?Furthermore,?it is a synthetic anabolic steroid developed in 1960 by Syntex Pharmaceuticals.

The other characteristics of this product can be summarized as:?(1)ACD/LogP: 4.22; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 3.17; (4)ACD/LogD (pH 7.4): 1.41; (5)ACD/BCF (pH 5.5): 85.45; (6)ACD/BCF (pH 7.4): 1.47; (7)ACD/KOC (pH 5.5): 424.82; (8)ACD/KOC (pH 7.4): 7.33; (9)#H bond acceptors: 3; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 2; (12)Index of Refraction: 1.589; (13)Molar Refractivity: 95.89 cm³; (14)Molar Volume: 284.2 cm³; (15)Polarizability: 38.01×10^-24 cm³; (16)Surface Tension: 50.3 dyne/cm; (17)Enthalpy of Vaporization: 83.9 kJ/mol; (18)Vapour Pressure: 1.23E-10 mmHg at 25°C; (19)Tautomer Count: 5; (20)Exact Mass: 332.235145; (21)MonoIsotopic Mass: 332.235145; (22)Topological Polar Surface Area: 57.5; (23)Heavy Atom Count: 24.

Preparation of Oxymetholone:?It can be obtained by hecogenin?or?tigogenin through?acetylation, reduction, ring opening, oxidation, hydrolysis, elimination, oxime, rearrangement, hydrolysis, addition reaction, oxidation, hydrolysis, condensation and other multi-step reaction.

Uses of Oxymetholone:?This drug was approved for human use by the FDA.?It is mainly used in the treatment of osteoporosis and anaemia, as well as stimulating muscle growth in undernourished or underdeveloped patients.?In addition, this drug is often used by bodybuilders and athletes, because it?is highly effective in promoting extensive gains in body mass, mostly by greatly improving protein synthesis. Many athletes also use oxymetholone as a method of protection for the joints under heavy loads.

When you are using this chemical, please be cautious about it as the following:
It has limited evidence of a carcinogenic effect, but it is possible risk of harm to the unborn child.?So people?should not breathe dust.?In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.?If you want to contact this product, you must wear suitable protective clothing, gloves and eye/face protection.?

People can use the following data to convert to the molecule structure.
1. SMILES:O=C4/C(=C\O)C[C@]1([C@@H](CC[C@@H]2[C@@H]1CC[C@]3([C@H]2CC[C@@]3(O)C)C)C4)C
2.?InChI:InChI=1/C21H32O3/c1-19-11-13(12-22)18(23)10-14(19)4-5-15-16(19)6-8-20(2)17(15)7-9-21(20,3)24/h12,14-17,22,24H,4-11H2,1-3H3/b13-12-/t14-,15+,16-,17-,19-,20-,21-/m0/s1

The following are the toxicity data which has been tested.

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
human	TDLo	oral	46mg/kg/14W-I (46mg/kg)	LIVER: LIVER FUNCTION TESTS IMPAIRED	JAMA, Journal of the American Medical Association. Vol. 240, Pg. 243, 1978. ?
rat	LD50	intraperitoneal	> 1gm/kg (1000mg/kg)	?	Drugs in Japan Vol. 6, Pg. 156, 1982.

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4.10 Toxicity: TDLo orl-hmn: 46 mg/kg/14W-I:LIV JAMAAP 240,243,78

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Carcinogenicity, Category 2

Reproductive toxicity, Category 2

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Warning
Hazard statement(s)	H351 Suspected of causing cancer H361 Suspected of damaging fertility or the unborn child
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

6. NMR Spectrum

Mass spectrum (electron ionization)

7. Computational chemical data

Molecular Weight: 332.484g/mol
Molecular Formula: C₂₁H₃₂O₃
Compound Is Canonicalized: True
XLogP3-AA: 4.4
Exact Mass: 332.23514488
Monoisotopic Mass: 332.23514488
Complexity: 596
Rotatable Bond Count: 0
Hydrogen Bond Donor Count: 2
Hydrogen Bond Acceptor Count: 3
Topological Polar Surface Area: 57.5
Heavy Atom Count: 24
Defined Atom Stereocenter Count: 7
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 1
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADcfB4MAAAAAAAAAAAAAAAAAAAAYAAAAAwYMAAAAAAAGDAAAAAGgAACAAAD0SggAICAAAAAgCIAoBSAAAAAAAgIAAAAAEAAEgAEBIAAQAAQAAEgAAAAIGIyPCPgAAAAAAAAACAAAQAACAAAYAADAAAAA==

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