4-Chlorodehydromethyltestosterone

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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, an East German pharmaceutical company. The patent registration took place in 1961. The idea of combining the structures of 4-chlorotestosterone and 1-dehydro-methyltestosterone originated 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

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During highly competitive time for the Olympics and national-level sporting events, East German experts looked for effective steroids to circumvent 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. People report that Turinabol use results in a “hard” look because it lacks the estrogenic properties which can lead to a 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 cannot 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 liver problems are all worth noting, the most serious concern is the effect it has on the blood lipid profile.^[3]

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

Further reading

• 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.