Basic information
- CAS
1424-00-6- Standard SMILES
C[C@H]1CC(=O)C[C@@H]2CC[C@H]3[C@@H]4CC[C@H](O)[C@@]4(C)CC[C@@H]3[C@]21C- InChIKey
UXYRZJKIQKRJCF-TZPFWLJSSA-N- Molecular formula
- C20H32O2
- Average molar mass
- 304.5 g/mol
- Monoisotopic mass
- 304.24023026
Names & identifiers
- Preferred name
- Mesterolone
- IUPAC
- (1S,5S,8R,9S,10S,13S,14S,17S)-17-hydroxy-1,10,13-trimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-one
- English name
- Mesterolone
- Molecular formula
- C20H32O2
- Molecular weight
- 304.47
Names & synonyms
Show more names
Database identifiers
- CAS
1424-00-6- PubChem CID
- 15020
- DTXSID
DTXSID90878533- ChEMBL
CHEMBL258918- ChEBI
CHEBI:135293- UNII
- 0SRQ75X9I9
- EC Number
- 215-836-3
- Nikkaji
- J7.487J
Properties
Computed structural properties
- XLogP
- 4.1
- Topological polar surface area
- 37.3 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 0
- Heavy atoms
- 22
- Formal charge
- 0
- Complexity
- 486
Experimental & physicochemical properties
Physicochemical properties
- Melting point
- 208 °C · 208 °C
- alpha
- 20 · D20 +17.6° (c = 0.875 in CHCl3)
- Boiling point
- 420.3 · 420.3±45.0 °C(Predicted)
- Density
- 1.156 g/cm3 · 1.156 g/cm3
- refractive index
- 17.6 ° · 17.6 ° (C=0.9, CHCl3)
- storage temp.
- 2 · 2-8°C
- solubility
- Practically insoluble in water, sparingly soluble in acetone, in ethyl acetate and in methanol
- pka
- 15.09 · 15.09±0.70(Predicted)
- Water Solubility
- 3 mg/L · 3mg/L at 20℃
- Merck
- 5916 · 5916
- Major Application
- forensics and toxicologypharmaceutical (small molecule)veterinary
- InChI
- InChI=1/C20H32O2/c1-12-10-14(21)11-13-4-5-15-16-6-7-18(22)19(16,2)9-8-17(15)20(12,13)3/h12-13,15-18,22H,4-11H2,1-3H3/t12-,13-,15-,16-,17-,18-,19-,20-/s3
- InChIKey
- UXYRZJKIQKRJCF-TZPFWLJSSA-N
- SMILES
- [C@@]12([H])CC[C@@]3([H])CC(=O)C[C@H](C)[C@]3(C)[C@@]1([H])CC[C@]1(C)[C@H](CC[C@@]21[H])O |&1:0,4,10,12,14,18,20,23,r|
- CAS DataBase Reference
- 1424 · 1424-00-6(CAS DataBase Reference)
- FDA UNII
- 0 SRQ75X9I9 · 0SRQ75X9I9
- ATC code
- 3 BB01 · G03BB01
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 24 · NA.24
- Symbol(GHS)
- 8 · GHS08,GHS09
- Signal word
- Danger
- Hazard statements
- 351 · H351-H360FD-H362-H411
- Precautionary statements
- 202 · P202-P260-P263-P264-P273-P308+P313
- PPE
- 95 · dust mask type N95 (US), Eyeshields, Gloves
- Hazard Codes
- Xn,T,F
- Risk Statements
- 20 · 20/21/22-38-19-11-61-60
- Safety Statements
- 22 · 22-24/25-36/37/39-45-53
- WGK Germany
- 3 · 3
- RTECS
- 8063400 · BV8063400
- HS Code
- 29372900 · 29372900
- Storage Class
- 6.1 C · 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- Hazard Classifications
- 2 Carc · Aquatic Chronic 2Carc. 2Lact.Repr. 1B
- DEA Controlled Substances
- 4000 CSA · CSCN: 4000CSA SCH: Schedule IIINARC: No
- REACH Registrations
- Inactive
Safety & regulation
GHS classification
GHS Classification
Warning
H302 (97.5%): Harmful if swallowed [Warning Acute toxicity, oral];H312 (97.5%): Harmful in contact with skin [Warning Acute toxicity, dermal];H332 (97.5%): Harmful if inhaled [Warning Acute toxicity, inhalation]
P261, P264, P270, P271, P280, P301+P317, P302+P352, P304+P340, P317, P321, P330, P362+P364, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 40 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.;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. For more detailed information, please visit ECHA C&L website.
Hazard information
Regulatory Information
DEA schedule III controlled substance
Status: Active Update: 30-03-2020 https://echa.europa.eu/registration-dossier/-/registered-dossier/12497
Regulatory information
Regulatory Information
DEA schedule III controlled substance
Status: Active Update: 30-03-2020 https://echa.europa.eu/registration-dossier/-/registered-dossier/12497
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- rtecs
- BV8063400
- hs_code
- 29372900
- risk_code
- 20/21/22-38-19-11-61-60
- Signal word
- Danger
- Symbol(GHS)
- GHS08,GHS09
- hazard_code
- Xn,T,F
- safety_code
- 22-24/25-36/37/39-45-53
- Storage Class
- 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- Hazard statements
- H351-H360FD-H362-H411
- REACH Registrations
- Inactive
- Hazard Classifications
- Aquatic Chronic 2Carc. 2Lact.Repr. 1B
- Precautionary statements
- P202-P260-P263-P264-P273-P308+P313
- DEA Controlled Substances
- CSCN: 4000CSA SCH: Schedule IIINARC: No
Chemistry & industry
Pharmacology
ATC Code
G03BB01
G - Genito urinary system and sex hormones;G03 - Sex hormones and modulators of the genital system;G03B - Androgens;G03BB - 5-androstanon (3) derivatives;G03BB01 - Mesterolone
QG - Genito urinary system and sex hormones;QG03 - Sex hormones and modulators of the genital system;QG03B - Androgens;QG03BB - 5-androstanon (3) derivatives;QG03BB01 - Mesterolone
Applications
DescriptionMesterolone (Item No. 21171) is an analytical reference standard categorized as an anabolic androgenic steroid. Formulations containing mesterolone have been used in patients with low testosterone or symptoms of aging male syndrome. Mesterolone cannot be aromatized to estrogens, unlike other androgens. This compound is the active ingredient in different pharmaceutical preparations that have been used medically but have also been widely applied in sports in order to improve athlete performance. Mesterolone is regulated as a Schedule III drug in the United States. This product is intended for research and forensic applications.
UsesMesterolone is a synthetic androgen and a dihydrotestosterone derivative. Mesterolone is rarely used for replacement therapies due to its weak androgenic activity.
General DescriptionMesterolone is a synthetic anabolic-androgenic steroid (AAS) and derivative of dihydrotestosterone (DHT). It is inactivated by 3α-hydroxysteroid dehydrogenase in skeleta muscules so it is considered a weak androgen. It is not a substrate for aromatase so it is not converted into estrogen. Mesterolone demonstrated to have minimal effect on sperm counts and levels of FSH or LH. Experiments of mesterolone serving as a potential treatment of depression are still undergoing.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers100 total
Additional notes
DefinitionChEBI: Mesterolone is a 3-oxo-5alpha-steroid. It is a structurally altered DHT hormone possessing the addition of a methyl group at the carbon one position. This allows the hormone to survive oral ingestion by protecting it from hepatic breakdown. This is one of the only oral anabolic steroids that is not C17-alpha alkylated (C17-aa) but instead carries the added methyl group.
Related reactions
Compound notes
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