434-22-0

Basic information

• Product Name: Nandrolone
• Synonyms: NADROLONE;NANDROLON;NANDROLONE;NORANDROSTENOLONE;NORTESTOSTERONE, 19-;(17beta)-estr-4-en-3-on;17-beta-hydroestr-4-en-3-one;17beta-hydroxy-19-nor-4-androsten-3-one
• CAS NO: 434-22-0
• Molecular Formula: C18H26O2
• Molecular Weight: 274.4
• EINECS: 207-101-0
• Product Categories: Miscellaneous Biochemicals;Steroids;Biochemistry;Hydroxyketosteroids;Intermediates & Fine Chemicals;Pharmaceuticals;Steroid and Hormone;API;nandrolone series;Inhibitors;Nandrolone ada@tuskwei.com whatsapp;8618031153937
• Mol File: 434-22-0.mol

Chemical Properties

• Melting Point: 120-125 °C
• Boiling Point: 357.38°C (rough estimate)
• Flash Point: 2℃
• Appearance: Crystalline solid
• Density: 1.0528 (rough estimate)
• Vapor Pressure: 2.25E-09mmHg at 25°C
• Refractive Index: 1.4800 (estimate)
• Storage Temp.: Controlled Substance, -20°C Freezer
• PKA: 15.06±0.40(Predicted)
• Water Solubility: 3.09g/L(25 oC)
• Merck: 6365
• BRN: 2055849
• CAS DataBase Reference: Nandrolone(CAS DataBase Reference)
• NIST Chemistry Reference: Nandrolone(434-22-0)
• EPA Substance Registry System: Nandrolone(434-22-0)

Safety Data

• Hazard Codes: Xn,T,F
• Statements: 20/21/22-64-40-61-60-36-11-38-19
• Safety Statements: 22-24/25-36/37/39-45-36/37-53-16
• RIDADR: UN 1648 3 / PGII
• WGK Germany: 3
• RTECS: KG7964000
• Hazardous Substances Data: 434-22-0(Hazardous Substances Data)

Usage

Chemical Properties

Crystalline Solid

Originator

Durabolin,Organon,US,1959

Uses

An anabolic steroid. Controlled substance (anabolic steroid)

Definition

ChEBI: A 3-oxo Delta4-steroid that is estr-4-en-3-one substituted by a beta-hydroxy group at position 17.

Manufacturing Process

An ice-cold solution of 1.5 grams of 19-nortestosterone and 1.5 ml of dry pyridine in 10 ml of dry benzene is prepared and a solution of 1.5 ml of β- phenylpropionyl chloride in 5 ml of dry benzene is added dropwise over a period of about 2 minutes with stirring. The resulting mixture is allowed to stand overnight under an atmosphere of nitrogen and then washed successively with cold 5% aqueous hydrochloric acid solution, cold 2.5% aqueous sodium hydroxide solution, and water. After drying over anhydrous sodium sulfate, the solvent is evaporated to give an almost colorless oil. Recrystallization from methanol gives white crystals of 19-nortestosterone 17- β-phenylpropionate, MP 91° to 92.5°C.

Therapeutic Function

Anabolic

Mechanism of action

Nandrolone facilitates formation of body muscle mass and strengthens the process of osseous tissue development. The main indications for using nandrolone, as well as other anabolic steroids, are abnormal protein anabolism, asthenia, diseases accompanied by protein loss, adrenal insufficiency, steroid diabetes, and prolonged condition of sluggishness.

Safety Profile

Experimental reproductiveeffects. When heated to decomposition it emits acridsmoke and irritating fumes.

Synthesis

Nandrolone, 17β-hydroxyester-4-en-3-one (29.1.7), is made from estradiol (28.1.17). The phenol hydroxyl group undergoes methylation by dimethylsulfate in the presence of sodium hydroxide, forming the corresponding methyl ether (29.3.1), and then the aromatic ring is reduced by lithium in liquid ammonia, which forms an enol ether (29.3.2). Hydrolyzing this compound with a mixture of hydrochloric and acetic acids leads to the formation of a keto group, and simultaneous isomerization of the double bond from C5–C10 to position C4–C5 gives the desired nandrolone (29.3.3) [16–19]. Upon necessity of using it in the form of acid esters, the product is acylated by corresponding acid derivatives.

InChI:InChI=1/C18H26O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h10,13-17,20H,2-9H2,1H3

Upstream product

• 571-25-5 17β-hydroxyandrost-5-en-3-one 
• 27428-41-7 3-oxo-7,7-(ethylenedioxy)-octanoic acid ethyl ester 
• 16271-49-1 (1S,7aS)-1-hydroxy-7a-methyl-2,3,7,7a-tetrahydro-1H-inden-5(6H)-one 
• 17553-86-5 (S)-Halos-Parish ketone 
• 24157-07-1 3β-tertiarybutoxy-1,2,3,3a,4,5,8,9,9aβ, 9bα-decahydro-6-[2-(2-methyl-1,3-dioxolan-2-yl)-ethyl]-3aβ-methyl-7H-benz[e]inden-7-one 
• 41878-38-0 (1S,7aS)-1-tert-butoxy-7a-methyl-1,2,3,6,7,7a-hexahydro-5H-inden-5-one 
• 1091-93-6 3-methoxy-17-hydroxyestra-2,5⁽¹⁰⁾-diene 
• 734-32-7 estra-4-ene-3,17-dione 
• 111-27-3 hexan-1-ol 
• 13943-33-4 iodomethylbenzoate 
• 891489-55-7 3-((Ξ)-2.3-dihydroxy-propyloxy)-estratrien-(1.3.5(10))-ol-(17β) 
• 73680-47-4 3β-acetoxy-19-norandrosta-1(10),5-dien-17-one 
• 6733-80-8 3-methoxy-13β-methylgona-1,3,5(10),8-tetraen-17β-yl acetate 
• 6733-79-5 3-methoxyestra-1,3,5(10),8(9)-tetraen-17β-ol 

Downstream Products

• 10093-54-6 17β-estradiol enanthate 
• 119599-12-1 4-chloro-17β-heptanoyloxy-estr-4-en-3-one 
• 13963-24-1 3,3-(ethylenedioxy)-17β-hydroxy-5-estrene 
• 15342-09-3 17β-hydroxyestr-5(10)-en-3-one ethylene acetal 
• 6193-99-3 3,3-(ethylenedioxy)-5(10)-estren-17-one 
• 64584-78-7 (8R,9S,10R,13S,14S,17S)-17-Hydroxy-13-methyl-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-3-one O-(2-nitro-phenyl)-oxime 
• 2590-41-2 6-dehydro-19-nortestosterone acetate 
• 472-54-8 19-norprogesterone 
• 13886-12-9 C₂₀H₃₀O₃ 
• 57-91-0 α-estradiol 
• 734-32-7 dl-estr-4-ene-3,17-dione 
• 16205-32-6 2-Fluoroestradiol 
• 23463-07-2 4-Hydroxy-17β-acetoxy-19-nor-androsten-(4)-on-(3) 
• 62-90-8 activin 

Relevant articles and documents

A New Synthesis of 19-Nor Steroids via 2,4-Dibromoestrogens

19-Nor steroids (7) and (8) have been synthesised via oxidation of 2,4-dibromoestrogens (1) and (2) with nitric acid followed by hydrogenation over palladium-on-charcoal and subsequent treatment with Nafion-H.

Microbial transformation of nandrolone decanoate by acremonium strictum

Estr-4-en-3,17-dione II, 17β-hydroxyestr-4-en-3-one III, 15α-hydroxyestr-4-en-3,17-dione IV, and 15α,17β-dihydroxyestr- 4-en-3-one V were produced by microbial transformation of nandrolone decanoate I in the culture of Acremonium strictum PTCC 5282. Bioconversion characteristics observed were ester hydrolysis, oxidation, and hydroxylation. Each microbial product was purified chromatographically and characterized on the basis of spectral data obtained from 1H-NMR, 13C-NMR, FT-IR, MS, and physical constants such as melting point and optical rotation.

Where does hydrolysis of nandrolone decanoate occur in the human body after release from an oil depot?

Long-term therapy of nandrolone (N) is recommended to increase mineral density and muscle strength. Using a parenteral sustained release drug formulation with nandrolone decanoate (ND), therapeutic N levels can be achieved and maintained. Until now, it is unknown if hydrolysis of ND into N occurs in tissue at the injection site or after systemic absorption. Therefore, hydrolysis studies were conducted to investigate the location and rate of ND hydrolysis after its release from the oil depot. ND hydrolysis was studied in porcine tissues, to mimic the human muscular and subcutaneous tissues. Additionally, the ND hydrolysis was studied in human whole blood, plasma and serum at a concentration range of 23.3–233.3?μM. ND hydrolysis only occurred in human whole blood. The hydrolysis did not start immediately, but after a lag time. The mean lag time for all studied concentrations was 34.9?±?2.5?min. Because of a slow penetration into tissue, hydrolysis of ND is found to be very low in surrounding tissue. Therefore the local generation of the active compound is clinically irrelevant. It is argued that after injection of the oil depot, ND molecules will be transported via the lymphatic system towards lymph nodes. From here, it will enter the central circulation and within half an hour it will hydrolyse to the active N compound.

Extreme electric fields power catalysis in the active site of ketosteroid isomerase

Enzymes use protein architecture to impose specific electrostatic fields onto their bound substrates, but the magnitude and catalytic effect of these electric fields have proven difficult to quantify with standard experimental approaches. Using vibrational Stark effect spectroscopy, we found that the active site of the enzyme ketosteroid isomerase (KSI) exerts an extremely large electric field onto the C=O chemical bond that undergoes a charge rearrangement in KSI's rate-determining step. Moreover, we found that the magnitude of the electric field exerted by the active site strongly correlates with the enzyme's catalytic rate enhancement, enabling us to quantify the fraction of the catalytic effect that is electrostatic in origin. The measurements described here may help explain the role of electrostatics in many other enzymes and biomolecular systems.

SYNTHESIS OF OPTICALLY ACTIVE (+)-19-NORTESTOSTERONE BY ASYMMETRIC BIS-ANNULATION REACTION

Michael reaction of 1,7-octadien-3-one with 2-methylcyclopentane-1,3-dione, followed by intramolecular aldol condensation promoted by L-amino acids produced the optically active (+)-4-(3-butenyl)-7a-methyl-5,6,7,7a-tetrahydro-indane-1,5-dione in high chem

Nitrobenzene as hydrogen acceptor in Pd/C-catalyzed hydrogen transfer reaction

Nitrobenzene was found to work as an efficient hydrogen acceptor in the oxidation of allylic alcohols to give the corresponding enones in high yields.

Preparation method of [3-14C] marked 17alpha-estradiol

The invention belongs to the technical field of synthesis of compounds marked by radioisotope 14C, and provides a preparation method of [3-14C] marked 17alpha-estradiol. The preparation method includes the following steps that 17beta-acylated elollactone and 14C marked acetylchloride serve as starting materials, and a condensation reaction, a primary hydrolysis reaction, a Mitsunobu reaction, an aromatization reaction and a secondary hydrolysis reaction are carried out to obtain [3-14C] marked 17alpha-estradiol. The method has the advantages that the synthesis cost is low, the line is short and the product yield is high. Besides, the preparation method is easy to operate and suitable for large-scale production.

Regio- and stereoselective reduction of 17-oxosteroids to 17β-hydroxysteroids by a yeast strain Zygowilliopsis sp. WY7905

The reduction of 17-oxosteroids to 17β-hydroxysteroids is one of the important transformations for the preparation of many steroidal drugs and intermediates. The strain Zygowilliopsis sp. WY7905 was found to catalyze the reduction of C-17 carbonyl group of androst-4-ene-3,17-dione (AD) to give testosterone (TS) as the sole product by the constitutive 17β-hydroxysteroid dehydrogenase (17β-HSD). The optimal conditions for the reduction were pH 8.0 and 30 °C with supplementing 10 g/l glucose and 1% Tween 80 (w/v). Under the optimized transformation conditions, 0.75 g/l AD was reduced to a single product TS with >90% yield and >99% diastereomeric excess (de) within 24 h. This strain also reduced other 17-oxosteroids such as estrone, 3β-hydroxyandrost-5-en-17-one and norandrostenedione, to give the corresponding 17β-hydroxysteroids, while the C-3 and C-20 carbonyl groups were intact. The absence of by-products in this microbial 17β-reduction would facilitate the product purification. As such, the strain might serve as a useful biocatalyst for this important transformation.

C-20 STEROID COMPOUNDS, COMPOSITIONS AND USES THEREOF TO TREAT TRAUMATIC BRAIN INJURY (TBI), INCLUDING CONCUSSIONS

The present invention relates to C-20 steroid compounds, compositions and methods of use thereof to treat, minimize and/or prevent traumatic brain injury (TBI), including severe TBI, moderate TBI and mild TBI, including concussions.

HELIX 12 DIRECTED STEROIDAL PHARMACEUTICAL PRODUCTS

Compounds having the structure or their salts: are used to treat or reduce le likelihood of acquiring androgen-dependent diseases, such as prostate cancer, benign prostatic hyperplasia, polycystic ovarian syndrome, acne, hirsutism, seborrhea, androgenic alopecia and male baldness. They can be formulated together with pharmaceutically acceptable diluent or carrier or otherwise made into any pharmaceutical dosage form. Some of these compounds having tissue-specific antiandrogenic activity and tissue-specific androgenic activity can be used to treat or reduce the risk of developing diseases related to loss of androgenic stimulation. Combinations with other active pharmaceutical agents are also disclosed.