4-Chlorodehydromethyltestosterone

4-Chlorodehydromethyltestosterone

Systematic (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
Clinical data
Pregnancy cat.	X (US) X (AUS)
Legal status	Schedule III (US) POM (UK)
Routes	Oral
Pharmacokinetic data
Bioavailability	100% Oral
Metabolism	Hepatic
Half-life	16 hours
Excretion	Undocumented
Identifiers
CAS number	2446-23-3
ATC code	?
PubChem	CID 98521
ChemSpider	88972 Y
Chemical data
Formula	C20H27ClO2
Mol. mass	334.8854
SMILES	eMolecules & PubChem
InChI 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 Y Key:AGUNEISBPXQOPA-XMUHMHRVSA-N Y
Y(what is this?)  (verify)

4-Chlorodehydromethyltestosterone, sold under the brand name Oral Turinabol, is an anabolic steroid. It is a chlor-substituted version of methandrostenolone (Dianabol). Turinabol was the first original product of Jenapharm, a pharmaceutical company from East Germany. The patent registration took place in 1961. The idea of combining the structures of 4-chlorotestosterone and 1-dehydro-methyltestosterone came from the chemist Albert Stachowiak. At the time this represented a unique dissociation of anabolic and androgenic effects after oral administration.^[1] The product had been introduced for clinical use in 1965.^[2]

Ergogenic use

During highly competitive time for the Olympics and national level sports, East German experts looked for effective steroids to circumvent these sports’ drug testing policies. They decided on a methylated version of 4-chlorotestosterone, also called Oral Turinabol. Oral Turinabol is often described as having properties between Dianabol and Anavar, with moderate anabolic effects and mild side effects. Turinabol displays anabolic tendencies that are approximately equal to or slightly greater than those of testosterone, while exhibiting little or no androgenic activity.

Because of this slower rate of gain, people who take Turinabol should not expect weight, strength, or muscle mass to increase dramatically, but the muscle and strength they do gain will be a “quality” gain. People report that Turinabol gives a “hard” look because it lacks the estrogenic properties which can lead to an undesirable puffy look. One of the other benefits of Turinabol is that the body quickly breaks it down and excretes it which make it beneficial for those who will be undergoing drug screening.

Due to the 4-chloro alteration, Oral Turinabol can't interact with the aromatase enzyme, so estrogenic side effects are diminished. However, it is interesting to note that some users report mild gynecomastia with oral turinabol alone. Whether this is due to the aromatization of a small amount of methyltestosterone left over from the manufacturing process or Oral Turinabol possibly having a small amount of direct action at the estrogen receptor is unclear. The 4-chloro alteration also prevents Oral Turinabol from interacting with the 5-alpha reductase enzyme, so conversion to a dihydro form is not possible. Even so, androgenic alopecia is still possible with higher doses eg (>40 mg/day), and not surprisingly, some erectile dysfunction will be present when Oral Turinabol is used alone despite a functional sex drive. Although mild acne, gas, indigestion, elevated liver enzymes, diminished production of leutinizing hormone, and natural testosterone are all worth noting, the most serious concern is the effect it has on the blood lipid profile.

Regardless of dosage amounts and length of regimens, Turinabol has one characteristic that should give caution to all of its users: It is 17-alpha alkylated which makes it hepatotoxic because it can't be easily broken down in the liver. Although some studies show liver enzymes to stay within normal ranges on a dose of ten milligrams per day, people using Oral Turinabol should keep usage limited to about six weeks to avoid liver damage. Additionally, Turinabol can lower the blood’s ability to clot, so special caution should be taken when using this steroid.

References

1. ^ Schwarz S, Onken D, Schubert A (July 1999). "The steroid story of Jenapharm: from the late 1940s to the early 1970s". Steroids 64 (7): 439–45. doi:10.1016/S0039-128X(99)00003-3. PMID 10443899. http://www.ingentaconnect.com/content/els/0039128x/1999/00000064/00000007/art00003. 
2. ^ Franke WW, Berendonk B (July 1997). "Hormonal doping and androgenization of athletes: a secret program of the German Democratic Republic government". Clin. Chem. 43 (7): 1262–79. PMID 9216474. http://www.clinchem.org/cgi/content/full/43/7/1262. 

Further reading

• [|Llewellyn, William] (January 2006). Anabolics: 2006 Edition. Body of Science. p. 410. ISBN 0-9679304-5-6. http://www.molecularnutrition.net. 

• Roberts, Anthony (January 2006). Anabolic Steroids: Ultimate Research Guide. Anabolic Books, LLC. p. 394. ISBN 1-59975-100-3. http://www.amazon.com/Anabolic-Steroids-Ultimate-Research-Guide. 

• Daniels, R. C. (February 1, 2003). The Anabolic Steroid Handbook. Richard C Daniels. p. 80. ISBN 0-9548227-0-6. http://www.amazon.com/Anabolic-Steroid-Handbook-R-Daniels/. 

• Roberts, Anthony (May 2006). Beyond Steroids. EF Publishing Inc.. p. 250. http://www.elitefitness.com/reports/beyondsteroids/. 

• Crabbe P, Pieraccini G, Bartolucci G, Moneti G, Van Peteghem C (2002). "Influence of Helix pomatia enzyme preparations on the oxidative conversion of some clostebol acetate metabolites in urine". J Anal Toxicol. 26 (2): 73–80. PMID 11916018.