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Trenbolone

HCID 25015
NotesReactions
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Substructure searchFind similar structures

Basic information

CAS
10161-33-8
Standard SMILES
C[C@]12C=CC3=C4CCC(=O)C=C4CC[C@H]3[C@@H]1CC[C@@H]2O
InChIKey
MEHHPFQKXOUFFV-OWSLCNJRSA-N
Molecular formula
C18H22O2
Average molar mass
270.4 g/mol
Monoisotopic mass
270.16197994

Overview

Trenbolone is a 3-oxo-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 an endocrine disruptor and a plant metabolite. It is a C18-steroid, a 17beta-hydroxy steroid, a 3-oxo-Delta(4) steroid and an anabolic androgenic steroid.

Names & identifiers

Preferred name
Trenbolone
IUPAC
(8S,13S,14S,17S)-17-hydroxy-13-methyl-2,6,7,8,14,15,16,17-octahydro-1H-cyclopenta[a]phenanthren-3-one
English name
Trenbolone
Molecular formula
C18H22O2
Molecular weight
270.37

Names & synonyms

Trenbolone10161-33-817beta-TrenboloneTrienbolone(+)-Trenbolone17-beta-TrenboloneTrenbolonum17-beta-Hydroxyestra-4,9,11-trien-3-oneDTXSID0034192RU 2341P53R4420TRDTXCID8014192
Show more names
trenbolon17β-TrenboloneParabolaTrenbolone enthanatetrenbolone (17β-hydroxyestr-4,9,11-trien-3-one)R 2580ru2341Tren 100
CHEBI:35018RU-2341trenbolonaRefChem:6506beta-Trenbolone17|A-TrenboloneTrembolona(8S,13S,14S,17S)-17-hydroxy-13-methyl-2,6,7,8,14,15,16,17-octahydro-1H-cyclopenta[a]phenanthren-3-one

Database identifiers

CAS
10161-33-8
PubChem CID
25015
DTXSID
DTXSID0034192
ChEMBL
CHEMBL197309、CHEMBL3182355
ChEBI
CHEBI:35018
UNII

Properties

Computed structural properties

XLogP
1.9
Topological polar surface area
37.3 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
2
Rotatable bonds
0
Heavy atoms
20
Formal charge
0
Complexity
566

Experimental & physicochemical properties

Drugs · 3 items

DEA NFLIS-Drug Category -> Steroids

Pharmaceutical

Pharmaceuticals -> Synthetic Cannabinoids or Psychoactive Compounds

Human DrugsPharmaceuticals
Endocrine DisruptorsPotential endocrine disrupting compound
Collision Cross Section · 2 items

192.3 Ų [M+Na]+ [CCS Type: DT; Buffer gas: N2; Ionization: ESI+; Dataset: TOXCAST; Source Identifier: DTXSID0034192]

163.3 Ų [M+H]+ [CCS Type: TW]

Physicochemical properties

Melting point
170 °C · 170°C
alpha
20 · D20 +19° (c = 0.45 in ethanol)
Boiling point
490.8 · 490.8±45.0 °C(Predicted)
Density
1.19 · 1.19±0.1 g/cm3(Predicted)
Flash point
2 ℃ · 2℃
storage temp.
2 · 2-8°C

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 4 items

Danger

H360 (95.9%): May damage fertility or the unborn child [Danger Reproductive toxicity]

P203, P280, P318, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 74 reports by companies from 6 notifications to the ECHA C&L Inventory.

Hazard information

Regulatory InformationREACH registered substance: (8S,13S,14S,17S)-17-hydroxy-13-methyl-2,6,7,8,14,15,16,17-octahydro-1H-cyclopenta[a]phenanthren-3-one (EC: 600-229-1)
Hazard Classes and CategoriesRepr. 1A (95.9%)

Safety data

wgk
3
rtecs
KG7752000
ridadr
UN 1648 3 / PGII
risk_code
60-36-20/21/22-11
Signal word
Danger
Symbol(GHS)
GHS08
hazard_code
T,Xn,F
safety_code
53-22-36/37/39-45-36/37-26-16
Storage Class
3 - Flammable liquids
Hazard statements
H351-H361d-H372
REACH Registrations
Active
Hazard Classifications
Acute Tox. 4 DermalAcute Tox. 4 InhalationAcute Tox. 4 OralEye Irrit. 2Flam. Liq. 2
Precautionary statements

Chemistry & industry

Pharmacology

MeSH Pharmacological ClassificationThese compounds stimulate anabolism and inhibit catabolism. They stimulate the development of muscle mass, strength, and power.

Uses & manufacturing

Use ClassificationPharmaceuticals
Applications · 2 items

DescriptionTrenbolone, 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.

UsesTrenbolone 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 methods · 1 item

PreparationTrenbolone 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

Related reactions

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
P53R4420TR
EC Number
600-229-1
Nikkaji
J8.986I
solubility
30 mg/ml; · DMF: 30 mg/ml; DMF:PBS (pH 7.2)(1:3): 0.25 mg/ml; DMSO: 20 mg/ml; Ethanol: 2 mg/ml
form
liquid
pka
14.73 · 14.73±0.40(Predicted)
Major Application
clinical testing
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+/s3
InChIKey
MEHHPFQKXOUFFV-OWSLCNJRSA-N
SMILES
[C@@]12([H])CC[C@H](O)[C@@]1(C)C=CC1=C3CCC(=O)C=C3CC[C@@]21[H] |&1:0,4,6,20,r|
CAS DataBase Reference
10161 · 10161-33-8(CAS DataBase Reference)
FDA 21 CFR
556.739 · 556.739
FDA UNII
53 R4420TR · P53R4420TR
EPA Substance Registry System
-4 · Estra-4,9,11-trien-3-one, 17-hydroxy-, (17.beta)- (10161-33-8)
UNSPSC Code
41116107 · 41116107
NACRES
24 · NA.24
Symbol(GHS)
8 · GHS08
Signal word
Danger
Hazard statements
351 · H351-H361d-H372
Precautionary statements
202 · P202-P260-P264-P270-P280-P308+P313
Hazard Codes
T,Xn,F
Risk Statements
60 · 60-36-20/21/22-11
Safety Statements
53 · 53-22-36/37/39-45-36/37-26-16
RIDADR
1648 · UN 1648 3 / PGII
WGK Germany
3 · 3
RTECS
7752000 · KG7752000
Storage Class
3 · 3 - Flammable liquids
Hazard Classifications
4 DermalAcute · Acute Tox. 4 DermalAcute Tox. 4 InhalationAcute Tox. 4 OralEye Irrit. 2Flam. Liq. 2
REACH Registrations
Active
P202-P260-P264-P270-P280-P308+P313

Upstream & downstream products

Upstream raw materials

Acetic anhydrideEthylenediamine tetrakis(propoxylate-block-ethoxylate) tetrolSodium tert-pentoxideMethanolAcetic acid

Downstream products

trendione

Suppliers100 total

北京华美互利生物化工010-56205725 · [email protected]
Shanghai Biolang Biotechnology Co., Ltd.+86-15970428662 +86-13397199602 · [email protected]
济南百隆化学有限公司[email protected] · [email protected]
艾吉析科技(上海)有限公司17717235263 · [email protected]
广州佳途科技股份有限公司81960175-877 18933936954 · [email protected]
陕西帕尼尔生物科技有限公司029-84385017-8003 13259417953 · [email protected]
长沙畋阳生物科技有限公司19558384994 19558384994 · [email protected]
广州隽唐科技有限公司020-36607679 13502246435 · [email protected]
南京世洲生物科技有限公司025-025-85560043 17301488900 · [email protected]
上海赛可锐生物科技有限公司021-58000709 13120558703 · [email protected]
武汉绿景丰华生物科技有限公司19972070065 · [email protected]
上海钰源生物化学有限公司021-13814116 13814116708 · [email protected]
陕西林奈生物化工有限公司15327269642 · [email protected]
LGM Pharma1-(800)-881-8210 · [email protected]
河北秒变生物科技有限公司17733850068
上海颖心实验室设备有限公司021-59178156 17002132182 · [email protected]
广东云星生物技术有限公司0751-18902340975/189023400307 18902340307 · [email protected]
上海瀚鸿科技股份有限公司021-54306202 13764082696 · [email protected]
Cangzhou Wanyou New Material Technology Co.,Ltd18631714998 · [email protected]
广东方信生物科技有限公司0751-2838688 13376594225 · [email protected]
InvivoChem中国13549236410 · [email protected]
上海维亦特生物科技有限公司15317051735 · [email protected]
凯试(上海)科技有限公司021-50135380 · [email protected]
Zhejiang J&C Biological Technology Co.,Limited+1-2135480471 · [email protected]
浙江佑宁医药有限公司15557595058
云南西力生物技术股份有限公司0871-65217109 · [email protected]
上海毕楷科技有限公司18516304666 · [email protected]
Xiamen AmoyChem Co., Ltd+86-86-5926051114 · [email protected]
陕西康多普生物科技有限公司184-2900-1220 18429001220 · [email protected]
广州普罗艾森生物医药有限公司19098059326 · [email protected]
TOKYO CHEMICAL INDUSTRY CO., LTD.03-36680489 · [email protected]
深圳振强药物研发有限公司0755-66853366 13670046396 · [email protected]
上海诺宝化工有限公司+86(0)21 60484900
南京生利德生物科技有限公司025-57798810 18652991625 · [email protected]
Xunteng International Trading Co.,Limited—
湖北鑫源顺医药化工有限公司13971561712, 13995564702, 027-50664929 · [email protected]
天津普西唐生物医药科技有限公司010-60605840 · [email protected]
上海寰川实业有限公司021-61478794 · [email protected]
Taizhou Xinen Biotechnology Co., Ltd.+8615068633455 · [email protected]
青岛海智微元生物科技有限公司18317699790 18317699790 · [email protected]
池州凯隆进出口贸易有限公司[email protected]
ALB Technology Limited702-983-3769 · [email protected]
石家庄通洋进出口有限公司[email protected]
Wuhan Biocar Bio-Pharm Co., Ltd.86 15387057351 · [email protected]
广东泰博医药科技有限公司15557595058 15557595058 · [email protected]
武汉鑫儒化工有限公司15927387915 15337108568 · [email protected]
安耐吉化学&3A(安徽泽升科技股份有限公司)400-0056266 · [email protected]
Shijiazhuang Erche Biotechnology Co., Ltd8613343119830 13343119830 · [email protected]
湖北辰心化工有限公司17362916295 · [email protected]
艾吉析科技(上海)有限公司17717235263 17717235263 · [email protected]
Additional notes · 1 item

DefinitionChEBI: 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.