Mesterolone

HCID 15020

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

MesteroloneAndrovironProviron1424-00-6TestiwopSH 723MesterolonaMesterolonum17beta-Hydroxy-1alpha-methyl-5alpha-androstan-3-oneSH-723Pro-VironNSC-75054
Show more names
mesterolonMESTERELONEmasterolonesh723NSC-7504NSC 75054mestoranummesteranum
0SRQ75X9I9DTXSID90878533(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-oneAndrostan-3-one, 17-hydroxy-1-methyl-, (1alpha,5alpha,17beta)-NSC750541alpha-methyl-5alpha-androstan-17beta-ol-3-one(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-oneRefChem:389115

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

Experimental & physicochemical properties

Melting Point204 °C
Physical DescriptionSolid

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

Safety & regulation

GHS classification

GHS Classification · 5 items

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 · 2 items

DEA schedule III controlled substance

Status: Active Update: 30-03-2020 https://echa.europa.eu/registration-dossier/-/registered-dossier/12497

Hazard Classes and CategoriesAcute Tox. 4 (97.5%);Acute Tox. 4 (97.5%);Acute Tox. 4 (97.5%)

Regulatory information

Regulatory Information · 2 items

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

Chemistry & industry

Pharmacology

ATC Code · 3 items

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

MeSH Pharmacological ClassificationThese compounds stimulate anabolism and inhibit catabolism. They stimulate the development of muscle mass, strength, and power.
Cellular LocationsExtracellular;Membrane
Applications · 3 items

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.

Suppliers100 total

Shanghai Biolang Biotechnology Co., Ltd.+86-15970428662 +86-13397199602 · [email protected]
艾吉析科技(上海)有限公司17717235263 · [email protected]
合肥翰刚医药科技有限公司+8618062405514 · [email protected]
上海哲研生物科技有限公司021-18017610038 18017610038 · [email protected]
湖北金梭生物科技有限公司00123456789 · [email protected]
Additional notes · 1 item

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

3 records

Compound notes

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