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Home> Encyclopedia >Pharmaceutical Intermediates>Pharmaceutical>Hormones and synthetic substitutes
Methenolone acetate structure
Methenolone acetate structure

Methenolone acetate

Iupac Name:[(5S,8R,9S,10S,13S,14S,17S)-1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl] acetate
CAS No.: 434-05-9
Molecular Weight:344.495
Modify Date.: 2022-10-30 19:33
Introduction: Methenolone acetate (Brand name: Primobolan) is a synthetic, orally active anabolic-androgenic steroid and dihydrotestosterone (DHT) derivative. It can be used for the treatment of bone marrow disease and anemia. Methenolone acetate is known for its higher therapeutic efficiency and lower hepatic toxicity compared with its 17 alpha-alkylated analogs. However, it is frequently abused in human sports because of its capability of increasing muscle strength as well as promoting performance and aggressiveness. It is capable of enhancing performance in racehorses. View more+
1. Names and Identifiers
1.1 Name
Methenolone acetate
1.2 Synonyms

(5α,17β)-17-(Acetyloxy)-1-methylandrost-1-en-3-one 17-(acetyloxy)-1-methyl-,(5-alpha,17-beta)-androst-1-en-3-on 17-beta-hydroxy-1-methyl-5-alpha-androst-1-en-3-onacetate 17-beta-hydroxy-1-methyl-5-alpha-androst-1-en-3-oneacetate 17b-Hydroxy-1-methyl-5a-androst-1-en-3-one acetate 17β-Hydroxy-1-methyl-5α-androst-1-en-3-one acetate 1-Methyl-17b-hydroxy-5a-androst-1-en-3-one acetate 1-Methyl-17β-hydroxy-5α-androst-1-en-3-one acetate 1-Methyl-17β-hydroxy-5α-androst-1-en-3-one-17β-acetate 1-Methyl-5α-androst-1-en-17β-ol-3-one acetate 5α-Androst-1-en-3-one, 17β-hydroxy-1-methyl-, acetate Androst-1-en-3-one, 17-(acetyloxy)-1-methyl-, (5α,17β)- METENOLONE ACETATE Methenolone 17-acetate METHENOLONE ACETATE nibal NSC 74226 Primobolan Primobolan Tablets Primobolone Primonabol SH 567 SH 567a SQ 16496

1.3 CAS No.
434-05-9
1.4 CID
252372
1.5 EINECS(EC#)
207-097-0
1.6 Molecular Formula
C22H32O3 (isomer)
1.7 Inchi
InChI=1S/C22H32O3/c1-13-11-16(24)12-15-5-6-17-18-7-8-20(25-14(2)23)21(18,3)10-9-19(17)22(13,15)4/h11,15,17-20H,5-10,12H2,1-4H3/t15-,17-,18-,19-,20-,21-,22-/m0/s1
1.8 InChkey
PGAUJQOPTMSERF-QWQRBHLCSA-N
1.9 Canonical Smiles
CC1=CC(=O)CC2C1(C3CCC4(C(C3CC2)CCC4OC(=O)C)C)C
1.10 Isomers Smiles
CC1=CC(=O)C[C@H]2[C@]1([C@H]3CC[C@]4([C@H]([C@@H]3CC2)CC[C@@H]4OC(=O)C)C)C
2. Properties
2.1 Density
1.1
2.1 Melting point
138-139°
2.1 Boiling point
441.2°Cat760mmHg
2.1 Refractive index
1.536
2.1 Flash Point
189.9°C
2.1 Precise Quality
344.23500
2.1 PSA
43.37000
2.1 logP
4.69600
2.1 Chemical Properties
White Solid
2.2 Color/Form
Powder
3. Use and Manufacturing
3.1 GHS Classification
Signal: Danger
GHS Hazard Statements
Aggregated GHS information provided by 16 companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
H351 (100%): Suspected of causing cancer [Warning Carcinogenicity]
H360 (100%): May damage fertility or the unborn child [Danger Reproductive toxicity]
H362 (100%): May cause harm to breast-fed children [Reproductive toxicity, effects on or via lactation]

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, P260, P263, P264, P270, P281, P301+P312, P308+P313, P330, P405, and P501
3.2 Usage
Methenolone acetate is an anabolic steroid. This is a controlled substance.
4. Safety and Handling
4.1 Safety
Moderately toxic by ingestion and intraperitoneal routes. An experimental teratogen. Other experimental reproductive effects. When heated to decomposition it emits acrid smoke and irritating fumes.
4.2 Specification

The Methenolone acetate has the cas register number 434-05-9, and it has the systematic name of (5alpha)-1-methyl-3-oxoandrost-1-en-17-yl acetate. This chemical is a kind of white or almost white crystalline powder. Besides, its product categories are including steroids.

The characteristics of this chemical are as follows: (1)ACD/LogP: 4.93; (2)ACD/LogD (pH 5.5): 4.92; (3)ACD/LogD (pH 7.4): 4.92; (4)ACD/BCF (pH 5.5): 3258.08; (5)ACD/BCF (pH 7.4): 3258.08; (6)ACD/KOC (pH 5.5): 11380.8; (7)ACD/KOC (pH 7.4): 11380.8; (8)#H bond acceptors: 3; (9)#Freely Rotating Bonds: 2; (10)Polar Surface Area: 43.37; (11)Index of Refraction: 1.536; (12)Molar Refractivity: 97.3 cm3; (13)Molar Volume: 311.8 cm3; (14)Polarizability: 38.57×10-24 cm3; (15)Surface Tension: 41.2 dyne/cm; (16)Density: 1.1 g/cm3; (17)Flash Point: 189.9 °C; (18)Enthalpy of Vaporization: 69.85 kJ/mol; (19)Boiling Point: 441.2 °C at 760 mmHg; (20)Vapour Pressure: 5.54E-08 mmHg at 25°C; (21)Exact Mass: 344.235145; (22)MonoIsotopic Mass: 344.235145; (23)Topological Polar Surface Area: 43.4; (24)Heavy Atom Count: 25; (25)Complexity: 635.

In addition, you could obtain the molecular structure by converting the following datas:
(1)SMILES:CC(=O)OC1CC[C@H]2[C@@H]3CC[C@H]4CC(=O)\C=C(\C)[C@]4(C)[C@H]3CC[C@]12CCopyCopied
(2)InChI:InChI=1/C22H32O3/c1-13-11-16(24)12-15-5-6-17-18-7-8-20(25-14(2)23)21(18,3)10-9-19(17)22(13,15)4/h11,15,17-20H,5-10,12H2,1-4H3/t15-,17-,18-,19-,20?,21-,22-/m0/s1

Below are the toxicity information of this chemical:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal > 2gm/kg (2000mg/kg) ? Drugs in Japan Vol. -, Pg. 1370, 1995.
mouse LD50 oral > 4gm/kg (4000mg/kg) ? Drugs in Japan Vol. -, Pg. 1370, 1995.
rat LD50 oral > 4gm/kg (4000mg/kg) ? Drugs in Japan Vol. -, Pg. 1370, 1995.

4.3 Toxicity

CHEMICAL IDENTIFICATION

RTECS NUMBER :
BV8408500
CHEMICAL NAME :
5-alpha-Androst-1-en-3-one, 17-beta-hydroxy-1-methyl-, acetate
CAS REGISTRY NUMBER :
434-05-9
LAST UPDATED :
199309
DATA ITEMS CITED :
5
MOLECULAR FORMULA :
C22-H32-O3
MOLECULAR WEIGHT :
344.54
WISWESSER LINE NOTATION :
L E5 B666 OV LUTJ A1 E1 FOV1 K1

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 :
4 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: 6,835,1982
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
4 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: 6,835,1982
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
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: 6,835,1982 ** REPRODUCTIVE DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
200 mg/kg
SEX/DURATION :
male 10 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Paternal Effects - prostate, seminal vesicle, Cowper's gland, accessory glands
REFERENCE :
ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 14,330,1964
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
60 mg/kg
SEX/DURATION :
female 17-20 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - urogenital system
REFERENCE :
AVBIB9 Advances in the Biosciences. (Pergamon Press Inc., Maxwell House, Fairview Park, Elmsford, NY 10523) V.1- 1967- Volume(issue)/page/year: 13,71,1974
5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Oral, Category 4

Carcinogenicity, Category 2

Reproductive toxicity, Category 1A

Reproductive toxicity, Additional category for effects on or via lactation

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word

Danger

Hazard statement(s)

H302 Harmful if swallowed

H351 Suspected of causing cancer

H360 May damage fertility or the unborn child

H362 May cause harm to breast-fed children

Precautionary statement(s)
Prevention

P264 Wash ... thoroughly after handling.

P270 Do not eat, drink or smoke when using this product.

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.

P260 Do not breathe dust/fume/gas/mist/vapours/spray.

P263 Avoid contact during pregnancy and while nursing.

Response

P301+P312 IF SWALLOWED: Call a POISON CENTER/doctor/\u2026if you feel unwell.

P330 Rinse mouth.

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

7. Synthesis Route
8. Precursor and Product
precursor:
1099-80-5
1099-80-5
9. Computational chemical data
  • Molecular Weight: 344.495g/mol
  • Molecular Formula: C22H32O3
  • Compound Is Canonicalized: True
  • XLogP3-AA: 4.4
  • Exact Mass: 344.23514488
  • Monoisotopic Mass: 344.23514488
  • Complexity: 635
  • Rotatable Bond Count: 2
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 3
  • Topological Polar Surface Area: 43.4
  • Heavy Atom Count: 25
  • 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: AAADcfB4MAAAAAAAAAAAAAAAAAAAAYAAAAAwYIAAAAAAAGDAAAAAGgAAAAAADxSggAICCAAABACIAqDSCAAAAAAgAAAACAEAAEgAABIAAQACAAAEgAAIAQOIyPCPgAAAAAAAAACAAAQAACAAAIAADAAAAA==
10. Question & Answer
  • Description Methenolone acetate, sold under the brand names Primobolan and Nibal, is an androgen and anabolic steroid (AAS) medication which is used mainly in the treatment of anemia due to bone marrow failure.It is taken by mouth.Although it was widely used in the past, the drug has mostly been di...
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