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10161-33-8

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10161-33-8 Usage

Description

Trenbolone, also known as trienolone or trienbolone, is a kind of anabolic androgenic steroid belonging to the 19-nortestosterone group. It can be supplied to veterinary medicine of livestock in order the boost muscle growth and appetite. It can also enhance the performance of athletes. It has several physiological effects: (1) enhance protein synthesis and nitrogen retention in the muscle tissues, which boost enhanced anabolism; (2) greatly promote insulin-like growth factor-1 (IGF-1) which is a highly effective anabolic hormone; (3) Greatly increase the red blood cell count to boost blood oxygenation which leads to improved muscular endurance; (4) Inhibit glucocorticoid hormones which inhibit the growth of muscle tissue and promote fat. (5) Improve food efficiency.

Chemical Properties

Yellow Solid

Originator

Parabolan,Negma,France,1980

Uses

Trenbolone is a controlled substance (anabolic steroid). It is a steroid used on livestock to increase muscle growth and appetite. To increase its effective half-life, trenbolone is administered as a prodrug as an ester conjugate such as [trenbolone acetate], trenbolone enanthate, or trenbolone cyclohexylmethylcarbonate. Plasma lipases then cleave the ester group in the bloodstream leaving free trenbolone.

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

Definition

ChEBI: Trenbolone is a 3-oxo-Delta(4) steroid that is estra-4,9,11-triene carrying an oxo group at position 3 and a hydroxy group at position 17beta. It is a synthetic anabolic steroid used for muscle growth in livestock. It has a role as a plant metabolite and an endocrine disruptor. It is a 3-oxo-Delta(4) steroid, a 17beta-hydroxy steroid, a C18-steroid and an anabolic androgenic steroid.

Brand name

[Trenbolone is INN and BAN.

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

10161-33-8SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name Trenbolone

1.2 Other means of identification

Product number -
Other names 17β-hydroxy-estra-4,9,11-trien-3-one

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:10161-33-8 SDS

10161-33-8Synthetic route

estrone-Δ5,10,Δ9,11-diene-17-ol-3-one
5218-51-9

estrone-Δ5,10,Δ9,11-diene-17-ol-3-one

trenbolone
10161-33-8

trenbolone

Conditions
ConditionsYield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane at 20 - 25℃; for 2h; Large scale;85%
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane at 40℃; Reagent/catalyst; Temperature;6.8 g
(8S,11R,13S,14S,17S)-11,17-Dihydroxy-13-methyl-1,2,6,7,8,11,12,13,14,15,16,17-dodecahydro-cyclopenta[a]phenanthren-3-one
117605-69-3

(8S,11R,13S,14S,17S)-11,17-Dihydroxy-13-methyl-1,2,6,7,8,11,12,13,14,15,16,17-dodecahydro-cyclopenta[a]phenanthren-3-one

trenbolone
10161-33-8

trenbolone

Conditions
ConditionsYield
With hydrogenchloride In chloroform
3-methoxy-estra-1,3,5(10)-triene-11α,17β-diol
10516-35-5

3-methoxy-estra-1,3,5(10)-triene-11α,17β-diol

trenbolone
10161-33-8

trenbolone

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 68 percent / Li, CH3OH / liquid ammonia / -70 °C
2: 70 percent / CH3CO2H / methanol
3: pyridine bromide-perbromide, pyridine
4: HCl / CHCl3
View Scheme
(8S,9S,11R,13S,14S,17S)-11,17-Dihydroxy-13-methyl-1,2,4,6,7,8,9,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-3-one
5210-14-0

(8S,9S,11R,13S,14S,17S)-11,17-Dihydroxy-13-methyl-1,2,4,6,7,8,9,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-3-one

trenbolone
10161-33-8

trenbolone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: pyridine bromide-perbromide, pyridine
2: HCl / CHCl3
View Scheme
(8S,9S,11R,13S,14S,17S)-3-Methoxy-13-methyl-4,6,7,8,9,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-11,17-diol
5210-13-9

(8S,9S,11R,13S,14S,17S)-3-Methoxy-13-methyl-4,6,7,8,9,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-11,17-diol

trenbolone
10161-33-8

trenbolone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 70 percent / CH3CO2H / methanol
2: pyridine bromide-perbromide, pyridine
3: HCl / CHCl3
View Scheme
C23H34O4

C23H34O4

trenbolone
10161-33-8

trenbolone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: potassium borohydride / methanol / 2 h / 20 - 25 °C / Large scale
2: sulfuric acid / water / 2 h / 20 - 25 °C / pH 7 / Large scale
3: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 2 h / 20 - 25 °C / Large scale
View Scheme
C23H36O4

C23H36O4

trenbolone
10161-33-8

trenbolone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sulfuric acid / water / 2 h / 20 - 25 °C / pH 7 / Large scale
2: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 2 h / 20 - 25 °C / Large scale
View Scheme
ethylene deltenone
5571-36-8

ethylene deltenone

trenbolone
10161-33-8

trenbolone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: butan-1-ol; potassium borohydride / 30 °C
2: sulfuric acid / acetone; water / 20 °C
3: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 40 °C
View Scheme
(8S,13S,14S,17S)-13-methyl-1,2,4,6,7,8,12,13,14,15,16,17-dodecahydrospiro[cyclopenta[a]phenanthrene-3,2'-[1,3]dioxolan]-17-ol
53303-91-6

(8S,13S,14S,17S)-13-methyl-1,2,4,6,7,8,12,13,14,15,16,17-dodecahydrospiro[cyclopenta[a]phenanthrene-3,2'-[1,3]dioxolan]-17-ol

trenbolone
10161-33-8

trenbolone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sulfuric acid / acetone; water / 20 °C
2: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 40 °C
View Scheme
trenbolone
10161-33-8

trenbolone

Trendione
4642-95-9

Trendione

Conditions
ConditionsYield
With Dess-Martin periodane In dichloromethane at 20℃; for 0.5h;76%
With oxalyl dichloride; dimethyl sulfoxide; triethylamine Swern oxidation;
2,3,4,5,6-pentafluorobenzyloxyamine hydrochloride
57981-02-9

2,3,4,5,6-pentafluorobenzyloxyamine hydrochloride

N-(heptafluorobutyryl)imidazole
32477-35-3

N-(heptafluorobutyryl)imidazole

trenbolone
10161-33-8

trenbolone

Δ9(10),11-19-nortestosterone pentafluorobenzyloxime heptafluorobutyryl ester

Δ9(10),11-19-nortestosterone pentafluorobenzyloxime heptafluorobutyryl ester

Conditions
ConditionsYield
With pyridine 1.) 60 deg C, 14 h, 2.) 60 deg C, 30 min; Multistep reaction;
acetic anhydride
108-24-7

acetic anhydride

trenbolone
10161-33-8

trenbolone

(8S,13S,14S,17S)-13-methyl-3-oxo-2,3,6,7,8,13,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-ylacetate

(8S,13S,14S,17S)-13-methyl-3-oxo-2,3,6,7,8,13,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-ylacetate

Conditions
ConditionsYield
With dmap In dichloromethane at 20 - 25℃; for 2h; Large scale;
With dmap In dichloromethane at 20℃; Reagent/catalyst; Solvent; Temperature;6 g

10161-33-8Related news

Assessing the fate and transformation by-product potential of Trenbolone (cas 10161-33-8) during chlorination07/25/2019

Chlorine disinfection is an effective means for managing microbiological activity during drinking water treatment and can eliminate a number of known organic contaminants. Trenbolone is an androgenic steroidal hormone used primarily as a growth stimulant in the animal feedstock industry and has ...detailed

Trenbolone (cas 10161-33-8) acetate metabolites promote ovarian growth and development in adult Japanese medaka (Oryzias latipes)07/23/2019

Trenbolone acetate, a synthetic androgen, has been used as a growth promoter in beef cattle in the US since 1987. While several teleost studies have investigated the masculinization effects of the metabolite 17β-trenbolone, few have focused on the reproductive impacts of all three trenbolone ac...detailed

Transformation kinetics of Trenbolone (cas 10161-33-8) acetate metabolites and estrogens in urine and feces of implanted steers07/21/2019

Biotransformation of trenbolone acetate metabolites and estrogens derived from animal feeding operations in soils, waste storage systems, and in land applied manure has been well characterized. Yet recent data demonstrate potential for steroid transport into the environment directly from feedyar...detailed

Detection and quantification of metastable photoproducts of Trenbolone (cas 10161-33-8) and altrenogest using liquid chromatography–tandem mass spectrometry07/17/2019

Here, we developed a novel and sensitive method for the detection and quantification of metastable trenbolone and altrenogest photoproducts in agricultural receiving waters based on solid phase extraction (SPE) and liquid chromatography-tandem mass spectrometry (LC–MS/MS). Primary method analyt...detailed

10161-33-8Relevant articles and documents

NEW APPROACH TO SYNTHESIS OF TRENBOLONE

Pestovskii, S. N.,Ananchenko, S. N.,Rzheznikov, V. M.,Zaitseva, T. S.

, p. 263 - 264 (1988)

-

Method for preparing pufferone acetate (by machine translation)

-

, (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)

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