4-Chlorodehydromethyltestosterone

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for 4-Chlorodehydromethyltestosterone are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is the 4-Chlorodehydromethyltestosterone?

The molecule 4-Chlorodehydromethyltestosterone presents a molecular formula of C20H27ClO2 and its IUPAC name is (8R,9S,10R,13S,14S,17S)-4-chloro-17-hydroxy-10,13,17-trimethyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-3-one.

Chlorodehydromethyltestosterone (CDMT; brand names Androctonus, Androxon, Hemogenin, Lonavar, Oxygonum, Turinabol) is an anabolic steroid. It is a chlor-substituted version of metandrostenolone (Dianabol). CDMT was one of the first anabolic steroids developed and used clinically..

CDMT was first synthesized in 1960 by a team of researchers at GDR’s Institute of Sports Medicine. The drug was developed as an oral anabolic agent for the treatment of muscle wasting in patients with chronic illnesses. CDMT was shown to be effective in the treatment of muscle wasting and was used clinically for this purpose until the early 1990s when it was replaced by more modern anabolic agents..

CDMT is a potent anabolic steroid with androgenic activity. The anabolic effects of CDMT are mediated by its binding to androgen receptors. The androgenic effects of CDMT are mediated by its 5α-reduced metabolite, 5α-dihydrochloromethyltestosterone (DHCMT)..

CDMT is no longer approved for clinical use and is only available as a black market drug..

The most common side effects of CDMT include masculinization (virilization) in women, acne, and increased hair growth. Other potential side effects include liver toxicity and cardiovascular risks..

CDMT is a controlled substance in many countries and its possession and use without a prescription is illegal..

3D structure

Cartesian coordinates

Geometry of 4-Chlorodehydromethyltestosterone in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

4-Chlorodehydromethyltestosterone AGUNEISBPXQOPA-XMUHMHRVSA-N chemical compound 2D structure molecule svg
4-Chlorodehydromethyltestosterone

 

Molecule descriptors

 
IUPAC name(8R,9S,10R,13S,14S,17S)-4-chloro-17-hydroxy-10,13,17-trimethyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-3-one
InChI codeInChI=1S/C20H27ClO2/c1-18-9-8-16(22)17(21)15(18)5-4-12-13(18)6-10-19(2)14(12)7-11-20(19,3)23/h8-9,12-14,23H,4-7,10-11H2,1-3H3/t12-,13+,14+,18-,19+,20+/m1/s1
InChI KeyAGUNEISBPXQOPA-XMUHMHRVSA-N
SMILESC[C@]12C=CC(=O)C(Cl)=C1CC[C@@H]1[C@@H]2CC[C@@]2(C)[C@H]1CC[C@]2(C)O

Other names (synonyms)

IUPAC nomenclature provides a standardized method for naming chemical compounds. Although this system is widely used in chemistry, many chemical compounds have also other names commonly used in different contexts. These synonyms can come from a variety of sources and are used for a variety of purposes.

One common source of synonyms for chemical compounds is the common or trivial names, assigned on the basis of appearance, properties, or origin of the molecule.

Another source of synonyms are historical or obsolete names employed in the past, however replaced nowadays by more modern or standardized names.

In addition to common and historical names, chemical compounds may also have synonyms that are specific to a particular field or industry.

  • (17b)-4-chloro-17-hydroxy-17-methyl-Androsta-1,4-dien-3-one
  • (1S,2R,10R,11S,14S,15S)-6-chloro-14-hydroxy-2,14,15-trimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6-dien-5-one
  • (8R,9S,10R,13S,14S,17S)-4-chloro-17-hydroxy-10,13,17-trimethyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-3-one
  • 1-Dehydro-4-chloro-17-methyltestosterone
  • 1-Dehydro-4-chloro-17a-methyltestosterone
  • 2446-23-3
  • 4-CHLORO-17.ALPHA.-METHYL-17.BETA.-HYDROXYANDROSTA-1,4-DIEN-3-ONE
  • 4-CHLORO-17.BETA.-HYDROXY-17.ALPHA.-METHYL-5.ALPHA.-ANDROSTA-1,4-DIEN-3-ONE
  • 4-CHLORO-17.BETA.-HYDROXY-17.ALPHA.-METHYLANDROST-1,4-DIEN-3-ONE
  • 4-Chlordehydromethyltestosterone
  • 4-Chloro-1,2-dehydro-17a-methyltestosterone
  • 4-Chloro-1-dehydro-17-methyltestosterone
  • 4-Chloro-1-dehydro-methyltestosterone
  • 4-Chloro-1-dehydromethyltestosterone
  • 4-Chloro-17a-methyl-17b-hydroxyandrosta-1,4-dien-3-one
  • 4-Chloro-17a-methyl-andro-1,4-diene-3,17b-diol
  • 4-Chloro-17alpha-methyl-17beta-hydroxy-1,4-androstadiene-3-one
  • 4-Chloro-17b-hydroxy-17a-methyl-5a-androsta-1,4-dien-3-one
  • 4-Chloro-methandienone
  • 4-Chlorodehydromethyltestosterone
  • 4-Chlorodianabol
  • 4-Chloromethandienone
  • 4-chlordehydromethyl testosterone
  • 4-chloro-17a-methyl-17b-hydroxy-1,4-androstadiene-3-one
  • 4-chloro-17b-hydroxy-17-methyl-Androsta-1,4-dien-3-one
  • 4-chloro-17beta-hydroxy-17alpha-methylandrosta-1,4-dien-3-one
  • 446C233
  • AM84830
  • Androsta-1,4-dien-3-one, 4-chloro-17-hydroxy-17-methyl-, (17.beta.)-
  • Androsta-1,4-dien-3-one, 4-chloro-17-hydroxy-17-methyl-, (17beta)-
  • BCP10777
  • CHLOROXYMESTERONE
  • Chlorodehydromethyltestosterone
  • D-4-Chloro-17 beta-hydroxy-3-oxo-17 alpha-methylandrosta-1,4-diene
  • Dehydrochlormethyltestosterone
  • Dehydrochloromethyltestosterone
  • Dehydrochloromethyltestosterone, 4-chloro-17.beta.-hydroxy-17.alpha.-methyl-androst-1,4-dien-3-one
  • J507.800H
  • Oral turinabol
  • Oral-Turinabol
  • Q909987
  • T-BOL
  • TBOL
  • Turinabol - oral
  • Turinabol-oral
  • ZPZ473F40K
  • h_48_dehydrochlormethyltestosterone

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC4026419
  • UNII-ZPZ473F40K
  • DTXSID10179216
  • CHEBI:166768
  • SCHEMBL3366383

Physico-Chemical properties

IUPAC name(8R,9S,10R,13S,14S,17S)-4-chloro-17-hydroxy-10,13,17-trimethyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-3-one
Molecular formulaC20H27ClO2
Molecular weight334.88
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity94.53
LogP4.6
Topological polar surface area37.3

LogP and topological polar surface area (TPSA) values were estimated using Open Babel software.

The n-octanol/water partition coeficient (Kow) data is applied in toxicology and drug research. Kow values are used, to guess the environmental fate of persistent organic pollutants. High partition coefficients values, tend to accumulate in the fatty tissue of organisms. Molecules with a log(Kow) (or LogP) greater than 5 are considered to bioaccumulate.

TPSA values are the sum of the surface area over all polar atoms or molecules, mainly oxygen and nitrogen, also including hydrogen atoms.

In medicinal chemistry, TPSA is used to assess the ability of a drug to permeabilise cells.

For molecules to penetrate the blood-brain barrier (and act on receptors in the central nervous system), TPSA values below 90 Å2 are required. Thus, molecules with a polar surface area greater than 140 Å2 tend to be poorly permeable to cell membranes.