Basic information
- Name:
Androstan-3-one,17-hydroxy-2-(hydroxymethylene)-17-methyl-, (5a,17b)-
- Superlist Name:
- Oxymetholone
- CAS No.:
434-07-1
- Molecular Structure:

- Formula:
- C21H32O3
- Synonyms:
- 5a-Androstan-3-one,17b-hydroxy-2-(hydroxymethylene)-17-methyl- (6CI,8CI);17-Beta-Hydroxy-2-hydroxymethylene-17-alpha-methyl-3-androstanone;17a-Methyl-2-hydroxymethylene-17-hydroxy-5a-androstan-3-one;17b-Hydroxy-2-(hydroxymethylene)-17a-methyl-5a-androstan-3-one;2-Hydroxymethylene-17a-methyl-17b-hydroxy-3-androstanone;2-Hydroxymethylene-17a-methylandrostan-17b-ol-3-one;2-Hydroxymethylene-17b-hydroxy-17a-methyl-5a-androstan-3-one;Adroyd;Anadrol;Anapolan 50;Anapolon;Anasteron;Anasteronal;Anasterone;Becorel;C.I. 406;HMD;NSC-26198;Nastenon;Oxymethenolone;Oxymetholone;Pardroyd;Plenastril;Protanabol;Roboral;Synasteron;Synasteron 50;
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History
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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