10161-33-8 Usage
Uses
Used in Livestock Industry:
Trenbolone is used as an anabolic steroid for livestock to increase muscle growth and appetite. It is administered as a prodrug in the form of ester conjugates, such as trenbolone acetate, trenbolone enanthate, or trenbolone cyclohexylmethylcarbonate. Plasma lipases then cleave the ester group in the bloodstream, leaving free trenbolone to exert its effects.
Used in Athletic Performance Enhancement:
Trenbolone is also used by athletes to enhance their performance. As a controlled substance, it is known for its ability to boost muscle growth, improve endurance, and increase strength. However, it is important to note that the use of trenbolone for athletic performance enhancement may be subject to regulations and restrictions depending on the jurisdiction and the specific sport.
Originator
Parabolan,Negma,France,1980
Preparation
Trenbolone synthesis: To a cold mixture of 47.9 g 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) in 375 mL anhydrous methylene chloride (DCM), a solution of 54.9 g compound (II-a) and 11.5 mL acetic acid in 150 mL anhydrous DCM is added dropwise under stirring, while keeping the internal temperature at -5 °C. The addition funnel is rinsed with 25 mL DCM and this aliquot is added to the reaction mixture. After 4 hours, reaction conversion reaches 99.25% by HPLC. The reaction mixture is quenched by addition of a solution composed of 5.7 g of Na2S2O5, 50 mL water and 10 mL MeOH. The obtained slurry is warmed to 15-23°C and left stirring for 0.5 h, after which it was filtered. The filter cake is washed with 2x40 mL DCM and the solid discarded. The obtained biphasic mixture is separated, and the organic phase washed twice with a solution of 100 mL water, 10 mL MeOH and 3.9 g of NaHCO3. The phases are separated, and the organic layer washed one final time with a solution of 100 mL water, 10 mL MeOH and 3.9 g of NaHCO3. The combined solution is concentrated with stirring to 150 mL (total volume) under vacuum, keeping the internal temperature below 30 °C. To the resulting solution, 150 mL of acetone are added, and the obtained mixture concentrated under vacuum to 150 mL (total volume) again, keeping the internal temperature below 30 °C. This addition/concentration protocol is repeated 3 times. The resulting suspension is cooled to 0 °C and kept at this temperature for 0.5 h with stirring, after which it is filtered, and the filter cake is washed twice with 50 mL cold acetone. The wet solid is dried at 40 °C under vacuum to give Trenbolone in 76% yield and 98.2 % A/A purity by HPLC.Synthesis of Trenbolone acetate
Therapeutic Function
Anabolic steroid
Side effects
Trenbolone's side effects aren't only physical but also mental, with users commonly reporting feeling increasingly: irritable, anxious, paranoid and depressed (than on other steroids).Such side effects can be linked to Trenbolone having a stimulating effect on the central nervous system, causing an increase in adrenaline output and thus shifting Tren-users into a state of fight or flight mode.
Safety Profile
When heated to
decomposition it emits acrid smoke and
irritating fumes.
References
https://en.wikipedia.org/wiki/Trenbolonehttps://www.steroid.com/Trenbolone.phpŠkorjanc, D, M. Brus, and I. Vojtic. "A short review of chain controlling systems in livestock production technology. " Agricultura (2005).
Check Digit Verification of cas no
The CAS Registry Mumber 10161-33-8 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,0,1,6 and 1 respectively; the second part has 2 digits, 3 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 10161-33:
(7*1)+(6*0)+(5*1)+(4*6)+(3*1)+(2*3)+(1*3)=48
48 % 10 = 8
So 10161-33-8 is a valid CAS Registry Number.
InChI:InChI=1/C18H22O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h8-10,15-17,20H,2-7H2,1H3/t15-,16+,17+,18+/m1/s1
10161-33-8Relevant articles and documents
A Chemoenzymatic Strategy for the Synthesis of Steroid Drugs Enabled by P450 Monooxygenase-Mediated Steroidal Core Modification
Peng, Yaqin,Gao, Chenghua,Zhang, Zili,Wu, Shijie,Zhao, Jing,Li, Aitao
, p. 2907 - 2914 (2022/03/03)
The synthesis of steroid drugs by multistage modifications of the steroidal core is challenging since site-specific and selective modification is essentially required, which is often difficult or complicated for chemocatalysis. For example, the synthesis of Trenbolone (3), a versatile anabolic-androgenic steroid, relies on a four-step chemical procedure on its core modifications of estra-4,9-diene-3,17-dione (1). Here, we have designed a two-step chemoenzymatic strategy that includes a biocatalytic one-pot C11-hydroxylation/17β-ketoreduction of 1 with a computationally designed P450 monooxygenase and an appropriate 17-ketosteroid reductase to generate 11α-OH-9(10)-dehydronandrolone (2a) as an intermediate followed by chemical dehydration to introduce the double bond at carbons 11 and 12 with the formation of Trenbolone (3). To obtain a highly active and C11-selective enzyme, molecular dynamics simulations were performed, uncovering a crucial role of water molecules for substrate recognition and targeted hydroxylation of steroids. Moreover, Trenbolone is further subjected to esterification to produce Trenbolone acetate (9) that has been widely used in veterinary medicine. Finally, our approach enables the regio- and stereoselective synthesis of both steroid drugs 3 and 9 on a (nearly) gram scale with 83-91% isolated yields, showing great potential for industrial applications.
Method for preparing pufferone acetate (by machine translation)
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, (2019/11/21)
The invention discloses a method for preparing pufferone acetate, and belongs to the technical field of preparation and processing of hormone drugs. The process is carried out 3 - with ethylenedioxy estra-Δ. 5,10 , Δ9,11 -17-ketone is a starting raw material, and the preparation of the 3 botanerone acetate is carried out by 17 reducing the position of the ketone as an alcohol, hydrolyzing the position of the furanone, the 17 oxidative dehydrogenation, and the alcohol acetylation. The method has the advantages of cheap and easily available raw materials, simple reaction control, few byproducts, easy purification and high total yield, has extremely high competitiveness in production cost and operability, is suitable for industrial large-scale production and has good economic benefits. (by machine translation)
Synthesis method of trenbolone acetate
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Paragraph 0008; 0025; 0030; 0031, (2018/05/30)
The invention provides a synthesis method of trenbolone acetate. The synthesis method comprises the following steps: step 1), dissolving a 4,9 ring-opening object (I) into methanol; adding potassium borohydride fractionally at 20 to 25 DEG C; after adding the potassium borohydride, carrying out heat preservation and reacting until a TLC (Thin-Layer Chromatography) analysis raw material is completely reacted, so as to obtain a compound (II); step 2), adding diluted acid into a reaction system for finishing reaction of step 1) and regulating the pH (Potential of Hydrogen) value to be neutral; dropwise adding dilute sulfuric acid and carrying out water separation to obtain 17beta-hydroxy-estra-5(10),9(11)-diene-3-one (III); step 3) dissolving the compound (III) into dichloromethane and addingDDQ (2,3-dichloro-5,6-dicyano-1,4-benzoquinone) and completely reacting; filtering; washing filtrate and combining a water layer; extracting the water layer by the dichloromethane; combining all dichloromethane layers; dehydrating, vacuum concentrating and drying to obtain trenbolone (IV); step 4) dissolving the trenbolone (IV) into the dichloromethane; adding DMAP (4-dimethylamiopryidine) and acetic anhydride and completely reacting to obtain the trenbolone acetate.
