NP-MRD: Showing NP-Card for 4-Chloromethandienone (NP0334732)

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Record Information

Version

2.0

Created at

2024-09-10 19:43:23 UTC

Updated at

2024-09-10 19:43:24 UTC

NP-MRD ID

NP0334732

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-Chloromethandienone

Description

4-Chloromethandienone, also known as 4-chlorodianabol or CDMT, belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans. 4-Chloromethandienone is an extremely weak basic (essentially neutral) compound (based on its pKa). The doping was done in secret; it was only in the 1990s that Franke and Berendonk looked closely at the original archived information and discovered the true scope of just how well-planned and successful the doping regime had been (in terms of medal success and world record performances). Following allegations by the German documentary of widespread doping the IOC kicked off a reanalysis of Beijing 2008 and London 2012 samples for all sports. Weightlifters and sprinters in particular were found to have used CDMT. The idea of combining the structures of 4-chlorotestosterone (clostebol) and metandienone originated from the chemist Albert Stachowiak. It is the 4-chloro-substituted derivative of metandienone (dehydromethyltestosterone). The doping program was run by the East German Government from about 1968 until 1989 when the GDR collapsed. CDMT was the key steroid administered to approximately 10,000 athletes from East Germany (GDR) as secret official policy, often without their knowing the nature of the "vitamins" they were forced to take. Most of the doped athletes coming from Russia, Ukraine, and Belarus. The product had been introduced for clinical use from 1965 until 1994 when its production was discontinued. 4-Chloromethandienone was first documented in 1999 (PMID: 10526287). ChlorodehydromethyltestosteroneCDMT was the first original product of Jenapharm, an East German pharmaceutical company.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02231219572D          

 26 29  0  0  1  0            999 V2000
   20.7276  -21.4148    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   25.2215  -17.6143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.2331  -20.5520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.6825  -18.0338    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   23.6825  -18.8588    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   22.9681  -19.2714    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   22.2535  -18.8588    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   24.4632  -17.7824    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   22.9681  -17.6213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4632  -19.1102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2535  -18.0338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9447  -18.4463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5028  -19.2770    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   22.9813  -20.1306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6374  -17.2990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2404  -20.5660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4962  -20.1363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4124  -17.0650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5091  -18.5647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7381  -18.8116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7244  -20.5899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9561  -19.2472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9492  -20.1423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9777  -19.4701    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   23.4744  -19.7547    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   22.8252  -18.5288    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1 21  1  0  0  0  0
  8  2  1  1  0  0  0
  3 23  2  0  0  0  0
  4  5  1  0  0  0  0
  4  8  1  0  0  0  0
  4  9  1  0  0  0  0
  4 15  1  1  0  0  0
  5  6  1  0  0  0  0
  5 10  1  0  0  0  0
  5 24  1  6  0  0  0
  6  7  1  0  0  0  0
  6 14  1  0  0  0  0
  6 25  1  1  0  0  0
  7 11  1  0  0  0  0
  7 13  1  0  0  0  0
  7 26  1  6  0  0  0
  8 12  1  0  0  0  0
  8 18  1  0  0  0  0
  9 11  1  0  0  0  0
 10 12  1  0  0  0  0
 13 17  1  0  0  0  0
 13 19  1  1  0  0  0
 13 20  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 21  2  0  0  0  0
 20 22  2  0  0  0  0
 21 23  1  0  0  0  0
 22 23  1  0  0  0  0
M  END


  Mrv0541 02231219572D          

 26 29  0  0  1  0            999 V2000
   20.7276  -21.4148    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   25.2215  -17.6143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.2331  -20.5520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.6825  -18.0338    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   23.6825  -18.8588    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   22.9681  -19.2714    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   22.2535  -18.8588    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   24.4632  -17.7824    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   22.9681  -17.6213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4632  -19.1102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2535  -18.0338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9447  -18.4463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5028  -19.2770    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   22.9813  -20.1306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6374  -17.2990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2404  -20.5660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4962  -20.1363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4124  -17.0650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5091  -18.5647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7381  -18.8116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7244  -20.5899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9561  -19.2472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9492  -20.1423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9777  -19.4701    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   23.4744  -19.7547    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   22.8252  -18.5288    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1 21  1  0  0  0  0
  8  2  1  1  0  0  0
  3 23  2  0  0  0  0
  4  5  1  0  0  0  0
  4  8  1  0  0  0  0
  4  9  1  0  0  0  0
  4 15  1  1  0  0  0
  5  6  1  0  0  0  0
  5 10  1  0  0  0  0
  5 24  1  6  0  0  0
  6  7  1  0  0  0  0
  6 14  1  0  0  0  0
  6 25  1  1  0  0  0
  7 11  1  0  0  0  0
  7 13  1  0  0  0  0
  7 26  1  6  0  0  0
  8 12  1  0  0  0  0
  8 18  1  0  0  0  0
  9 11  1  0  0  0  0
 10 12  1  0  0  0  0
 13 17  1  0  0  0  0
 13 19  1  1  0  0  0
 13 20  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 21  2  0  0  0  0
 20 22  2  0  0  0  0
 21 23  1  0  0  0  0
 22 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0334732

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12CC[C@](C)(O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=C(Cl)C(=O)C=C[C@]12C

> <INCHI_IDENTIFIER>
InChI=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_KEY>
AGUNEISBPXQOPA-XMUHMHRVSA-N

> <FORMULA>
C20H27ClO2

> <MOLECULAR_WEIGHT>
334.88

> <EXACT_MASS>
334.169957815

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
37.264815916736396

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2R,10R,11S,14S,15S)-6-chloro-14-hydroxy-2,14,15-trimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,6-dien-5-one

> <ALOGPS_LOGP>
4.11

> <JCHEM_LOGP>
4.032775772333333

> <ALOGPS_LOGS>
-4.77

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-0.5280914180307591

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
94.95259999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.75e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
oral turinabol

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1 Cl   UNK     0      38.692 -39.974   0.000  0.00  0.00          Cl+0
HETATM    2  O   UNK     0      47.080 -32.880   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      35.902 -38.364   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      44.207 -33.663   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      44.207 -35.203   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      42.874 -35.973   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      41.540 -35.203   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      45.665 -33.194   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      42.874 -32.893   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      45.665 -35.672   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      41.540 -33.663   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      46.563 -34.433   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      40.139 -35.984   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      42.898 -37.577   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      44.123 -32.291   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      41.515 -38.390   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      40.126 -37.588   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      45.570 -31.855   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      40.150 -34.654   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      38.711 -35.115   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      38.686 -38.434   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      37.251 -35.928   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      37.239 -37.599   0.000  0.00  0.00           C+0
HETATM   24  H   UNK     0      44.758 -36.344   0.000  0.00  0.00           H+0
HETATM   25  H   UNK     0      43.819 -36.875   0.000  0.00  0.00           H+0
HETATM   26  H   UNK     0      42.607 -34.587   0.000  0.00  0.00           H+0
CONECT    1   21                                                            
CONECT    2    8                                                            
CONECT    3   23                                                            
CONECT    4    5    8    9   15                                             
CONECT    5    4    6   10   24                                             
CONECT    6    5    7   14   25                                             
CONECT    7    6   11   13   26                                             
CONECT    8    2    4   12   18                                             
CONECT    9    4   11                                                       
CONECT   10    5   12                                                       
CONECT   11    7    9                                                       
CONECT   12    8   10                                                       
CONECT   13    7   17   19   20                                             
CONECT   14    6   16                                                       
CONECT   15    4                                                            
CONECT   16   14   17                                                       
CONECT   17   13   16   21                                                  
CONECT   18    8                                                            
CONECT   19   13                                                            
CONECT   20   13   22                                                       
CONECT   21    1   17   23                                                  
CONECT   22   20   23                                                       
CONECT   23    3   21   22                                                  
CONECT   24    5                                                            
CONECT   25    6                                                            
CONECT   26    7                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   58    0
END

View in JSmol

Synonyms

Value	Source
(17b)-4-Chloro-17-hydroxy-17-methyl-androsta-1,4-dien-3-one	HMDB
1-Dehydro-4-chloro-17-methyltestosterone	HMDB
1-Dehydro-4-chloro-17a-methyltestosterone	HMDB
4-Chloro-1,2-dehydro-17a-methyltestosterone	HMDB
4-Chloro-1-dehydro-17-methyltestosterone	HMDB
4-Chloro-1-dehydromethyltestosterone	HMDB
4-Chloro-17a-methyl-17b-hydroxyandrosta-1,4-dien-3-one	HMDB
4-Chloro-17b-hydroxy-17-methyl-androsta-1,4-dien-3-one	HMDB
4-Chloro-17b-hydroxy-17a-methyl-5a-androsta-1,4-dien-3-one	HMDB
4-Chlorodehydromethyltestosterone	HMDB
4-Chlorodianabol	HMDB
CDMT	HMDB
Oral-turinabol	HMDB
Turinabol-oral	HMDB
Dehydrochlormethyltestosterone	HMDB
D-4-Chloro-17 beta-hydroxy-3-oxo-17 alpha-methylandrosta-1,4-diene	HMDB
4-Chloro-methandienone	HMDB
Oral turinabol	HMDB

Chemical Formula

C₂₀H₂₇ClO₂

Average Mass

334.8800 Da

Monoisotopic Mass

334.16996 Da

IUPAC Name

(1S,2R,10R,11S,14S,15S)-6-chloro-14-hydroxy-2,14,15-trimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,6-dien-5-one

Traditional Name

oral turinabol

CAS Registry Number

Not Available

SMILES

[H][C@@]12CC[C@](C)(O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=C(Cl)C(=O)C=C[C@]12C

InChI Identifier

InChI=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 Key

AGUNEISBPXQOPA-XMUHMHRVSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Androstane steroids

Direct Parent

Androgens and derivatives

Alternative Parents

Substituents

Androgen-skeleton
3-oxo-delta-1,4-steroid
3-oxosteroid
17-hydroxysteroid
4-halo-steroid
Halo-steroid
Oxosteroid
Hydroxysteroid
Delta-1,4-steroid
Alpha-haloketone
Alpha-chloroketone
Cyclic alcohol
Tertiary alcohol
Cyclic ketone
Ketone
Chloroalkene
Haloalkene
Vinyl halide
Vinyl chloride
Alcohol
Organic oxide
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Organooxygen compound
Organochloride
Organohalogen compound
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	4.11	ALOGPS
logP	4.03	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Basic)	-0.53	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	94.95 m³·mol⁻¹	ChemAxon
Polarizability	37.26 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0004634

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB023389

KNApSAcK ID

Not Available

Chemspider ID

88972

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Chlorodehydromethyltestosterone

METLIN ID

Not Available

PubChem Compound

98521

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Froehner M, Fischer R, Leike S, Hakenberg OW, Noack B, Wirth MP: Intratesticular leiomyosarcoma in a young man after high dose doping with Oral-Turinabol: a case report. Cancer. 1999 Oct 15;86(8):1571-5. doi: 10.1002/(sici)1097-0142(19991015)86:8<1571::aid-cncr26>3.0.co;2-c. [PubMed:10526287 ]

Showing NP-Card for 4-Chloromethandienone (NP0334732)

MOL for NP0334732 (4-Chloromethandienone)

3D MOL for NP0334732 (4-Chloromethandienone)

3D SDF for NP0334732 (4-Chloromethandienone)

3D-SDF for NP0334732 (4-Chloromethandienone)

PDB for NP0334732 (4-Chloromethandienone)

3D PDB for NP0334732 (4-Chloromethandienone)

SMILES for NP0334732 (4-Chloromethandienone)

INCHI for NP0334732 (4-Chloromethandienone)

Structure for NP0334732 (4-Chloromethandienone)

3D Structure for NP0334732 (4-Chloromethandienone)