CAS 521-18-6 Dihydrotestosterone (HCID 10635)

Overview

17beta-hydroxy-5alpha-androstan-3-one is a 17beta-hydroxy steroid that is testosterone in which the 4,5 double bond has been reduced to a single bond with alpha-configuration at position 5. It has a role as an androgen, a mouse metabolite, a human metabolite and a Daphnia magna metabolite. It is a 3-oxo-5alpha-steroid, a 17beta-hydroxy steroid and a 17beta-hydroxyandrostan-3-one. It derives from a hydride of a 5alpha-androstane.

Names & identifiers

Preferred name: Dihydrotestosterone
IUPAC: (5S,8R,9S,10S,13S,14S,17S)-17-hydroxy-10,13-dimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-one
English name: Stanolone
Molecular formula: C19H30O2
Molecular weight: 290.45

Names & synonyms

STANOLONEAndrostanolonedihydrotestosterone521-18-6AnabolexAndractimAndroloneNeodrol4-DihydrotestosteroneAnaboleenProteinaStanaprol

Show more names

DHT5α-Dihydrotestosterone5α-DHT5α-androstan-17β-ol-3-oneStanolon

Protona5alpha-DihydrotestosteroneCristerona MB17beta-Hydroxy-5alpha-androstan-3-oneAndrostanolona5alpha-Androstan-17beta-ol-3-one5-alpha-DihydrotestosteroneTestosterone, dihydro-

Database identifiers

CAS: 521-18-6
PubChem CID: 10635
DTXSID: DTXSID9022364
ChEMBL: CHEMBL27769
ChEBI: CHEBI:16330
UNII: 08J2K08A3Y
EC Number: 208-307-3
Nikkaji: J39.503J

Properties

Computed structural properties

XLogP: 3.7
Topological polar surface area: 37.3 Å²
Hydrogen bond donors: 1
Hydrogen bond acceptors: 2
Rotatable bonds: 0
Heavy atoms: 21
Formal charge: 0
Complexity: 458

Experimental & physicochemical properties

Chemical ClassesHormone

Drugs · 3 items

DEA NFLIS-Drug Category -> Steroids

DEA Schedule III Controlled Substance -> Anabolic steroids

Pharmaceuticals -> Synthetic Cannabinoids or Psychoactive Compounds

LipidsLipids -> Sterol Lipids [ST] -> Steroids [ST02] -> C19 steroids (androgens) and derivatives [ST0202]

SpringerMaterials PropertiesChemical shift

LogP3.55

Human DrugsPharmaceuticals

Physicochemical properties

Melting point: 178 · 178-183 °C
alpha: 27 · 27 º
Boiling point: 372.52 °C · 372.52°C (rough estimate)
Density: 1.032 · 1.0320 (rough estimate)
refractive index: 1.4709 · 1.4709 (estimate)
Flash point: 9 ℃ · 9℃
storage temp.: 2 · 2-8°C
solubility: 1 mg/ml; · Acetonitrile: 1 mg/ml; Ethanol: 1 mg/ml; Methanol: 1 mg/ml
pka: 15.08 · 15.08±0.60(Predicted)
form: powder
biological source: synthetic
optical activity: 20 · [α]20/D +33±1°, c =1% in ethanol
Water Solubility: 344.3 g/L · 344.3g/L(temperature not stated)
Merck: 13 · 13,8872
BRN: 2056371 · 2056371
Major Application: forensics and toxicologypharmaceutical (small molecule)
InChI: 1S/C19H30O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h12,14-17,21H,3-11H2,1-2H3/t12-,14-,15-,16-,17-,18-,19-/m0/s1
InChIKey: NVKAWKQGWWIWPM-ABEVXSGRSA-N
SMILES: [H][C@@]12CC[C@@]3([H])[C@]4([H])CC[C@H](O)[C@@]4(C)CC[C@]3([H])[C@@]1(C)CCC(=O)C2
CAS DataBase Reference: 521 · 521-18-6(CAS DataBase Reference)
NCI Dictionary of Cancer Terms: androstanolone; DHT; dihydrotestosterone
FDA UNII: 8 J2K08A3Y · 08J2K08A3Y
NCI Drug Dictionary: dihydrotestosterone
ATC code: 14 AA01,G03BB02 · A14AA01,G03BB02
NIST Chemistry Reference: Stanolone(521-18-6)
EPA Substance Registry System: -3 · Androstan-3-one, 17-hydroxy-, (5.alpha.,17.beta.)- (521-18-6)
UNSPSC Code: 51111800 · 51111800
NACRES: 77 · NA.77
Symbol(GHS): 7 · GHS07,GHS08,GHS09
Signal word: Danger
Hazard statements: 302 · H302-H351-H360FD-H410
Precautionary statements: 202 · P202-P264-P270-P273-P301+P312-P308+P313
PPE: 3 · Eyeshields, Gloves, type P3 (EN 143) respirator cartridges
Hazard Codes: Xn,T,F
Risk Statements: 61 · 61-40-39/23/24/25-23/24/25-11
Safety Statements: 53 · 53-36/37/39-45-36/37-16
RIDADR: 1230 · UN1230 - class 3 - PG 2 - Methanol, solution
WGK Germany: 3 · 3
RTECS: 8052000 · BV8052000
Storage Class: 6.1 C · 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
Hazard Classifications: 4 OralAquatic · Acute Tox. 4 OralAquatic Acute 1Aquatic Chronic 1Carc. 2Repr. 1A
REACH Registrations: Inactive

Safety & regulation

GHS classification

GHS Classification · 4 items

Danger

H351 (98.3%): Suspected of causing cancer [Warning Carcinogenicity]

P203, P280, P318, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 60 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory Information · 2 items

DEA schedule III controlled substance

Status: Cease Manufacture Update: 31-10-2012 https://echa.europa.eu/registration-dossier/-/registered-dossier/12136

Hazard Classes and CategoriesCarc. 2 (98.3%)

Toxicology

Exposure RoutesBioavailability is very low (0-2%) following oral administration.

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).

Drug Induced Liver Injury · 4 items

Drug-Induced Liver Injury Severity and Toxicity (DILIst)

ANDROSTANOLONE

DILI Positive

DOI:10.1016/j.drudis.2019.09.022

USGS Health-Based Screening Levels for Evaluating Water-Quality · 3 items

Dihydrotestosterone

Hormone

Smith, C.D. and Nowell, L.H., 2024. Health-Based Screening Levels for evaluating water-quality data (3rd ed.). DOI:10.5066/F71C1TWP

Safety data

PPE: Eyeshields, Gloves, type P3 (EN 143) respirator cartridges
wgk: 3
rtecs: BV8052000
ridadr: UN1230 - class 3 - PG 2 - Methanol, solution
risk_code: 61-40-39/23/24/25-23/24/25-11
Signal word: Danger
Symbol(GHS): GHS07,GHS08,GHS09
hazard_code: Xn,T,F
safety_code: 53-36/37/39-45-36/37-16
Storage Class: 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
Hazard statements: H302-H351-H360FD-H410
REACH Registrations: Inactive
Hazard Classifications: Acute Tox. 4 OralAquatic Acute 1Aquatic Chronic 1Carc. 2Repr. 1A
Precautionary statements: P202-P264-P270-P273-P301+P312-P308+P313

Chemistry & industry

Pharmacology

ATC Code · 4 items

A - Alimentary tract and metabolism

G - Genito urinary system and sex hormones

QA - Alimentary tract and metabolism

QG - Genito urinary system and sex hormones

MeSH Pharmacological Classification · 1 item

Compounds that interact with ANDROGEN RECEPTORS in target tissues to bring about the effects similar to those of TESTOSTERONE. Depending on the target tissues, androgenic effects can be on SEX DIFFERENTIATION; male reproductive organs, SPERMATOGENESIS; secondary male SEX CHARACTERISTICS; LIBIDO; development of muscle mass, strength, and power.

Absorption, Distribution and ExcretionBioavailability is very low (0-2%) following oral administration.

Tissue LocationsAdipose Tissue

Cellular LocationsCytoplasm

Metabolite PathwaysAndrogen and Estrogen Metabolism

Uses & manufacturing

UsesDihydrotestosterone is an endogenously produced metabolite found in the human body. It is used in metabolic reactions, catabolic reactions or waste generation.

Use ClassificationPharmaceuticals

Applications · 3 items

DescriptionStanolone is well known as dihydrotestosterone (DHT), which is an endogenous androgen sex steroid and hormone. It is an agonist of the androgen receptor (AR). It plays important physiological role in sexual differentiation, maturation of the penis and scrotum, hair, sebum production and development and maintenance of the prostate gland and seminal vesicles. It is mainly used for the treatment of male hypogonadism, androgen deficiency of severe illness, androgen deficiency of ageing and microphallus in infancy.

UsesStanolone is a potent androgenic metabolite of testosterone that It is Controlled substance. It was created for the treatment of muscle wasting disease, and osteoporosis. It is a powerful anabolic steroid, which is similar to the body's naturally produced Dihydrotestosterone. Dihydrotestosterone (DHT) is generated by a 5-alpha reduction of testosterone. Unlike testosterone, DHT cannot be aromatized to estradiol therefore DHT is considered a pure androgenic steroid.

General DescriptionDihydrotestosterone (Item No. 15874) is an analytical reference standard categorized as an anabolic androgenic steroid. Anabolic steroids, including dihydrotestosterone, have been used to enhance physical performance in athletes. Dihydrotestosterone is regulated as a Schedule III compound in the United States. This product is intended for research and forensic applications.

Upstream & downstream products

Upstream raw materials

Selenium dioxide Sodium borohydride

Downstream products

5alpha-Androst-16-en-3-one 5.alpha.-Androstan-3-one, 17.beta.-hydroxy-2-(hydroxymethylene)-

Suppliers100 total

Shanghai Biolang Biotechnology Co., Ltd.+86-15970428662 +86-13397199602 · [email protected]

Hong Kong Tiansheng New Material Trading Co., Ltd+8617320695765 · [email protected]

INTATRADE GmbH+49 3493/605464 · [email protected]

Hebei shuoxi biotechnology co. LTD+8613081092107

河北展药生物科技有限公司15369953316 +8615369953316 · [email protected]

Additional notes · 1 item

DefinitionChEBI: Stanolone is a 17beta-hydroxy steroid that is testosterone in which the 4,5 double bond has been reduced to a single bond with alpha-configuration at position 5. It has a role as an androgen, a human metabolite, a Daphnia magna metabolite and a mouse metabolite. It is a 17beta-hydroxy steroid, a 17beta-hydroxyandrostan-3-one and a 3-oxo-5alpha-steroid. It derives from a hydride of a 5alpha-androstane.