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
• Article Data: 24

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

• 1089-78-7 17β-hydroxy-estr-5(10)-en-3-one 
• 734-32-7 estra-4-ene-3,17-dione 
• 10005-66-0 3-methoxy-13β-methylgona-1,3,5(10),9(11)-tetraen-17β-yl acetate 
• 86846-56-2 10β,17β-dihydroxy-5ξ-estran-3-one 
• 13943-33-4 iodomethylbenzoate 
• 1091-93-6 3-methoxy-17-hydroxyestra-2,5⁽¹⁰⁾-diene 
• 571-25-5 17β-hydroxyandrost-5-en-3-one 
• 6733-79-5 3-methoxyestra-1,3,5(10),8(9)-tetraen-17β-ol 
• 111-87-5 octanol 
• 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 

Downstream Products

• 1474-55-1 nandrolone benzoate 
• 10093-54-6 17β-estradiol enanthate 
• 119599-12-1 4-chloro-17β-heptanoyloxy-estr-4-en-3-one 
• 734-32-7 estra-4-ene-3,17-dione 
• 1434-85-1 17β-hydroxy-5α-estran-3-one 
• 21547-28-4 17β-hydroxy-5-methyl-19-nor-5β,9α,10β-androstan-3-one 
• 4146-29-6 6β,17β-dihydroxy-19-norandrost-4-en-3-one 
• 5949-49-5 6β-hydroxy-19-norandrostenedione 
• 131749-24-1 estr-4-en-3-one-17β-O-glucuronide 
• 294213-86-8 3α-hydroxy-5α-estran-17-one glucuronide 
• 294213-87-9 3α-hydroxy-5β-estran-17-one glucuronide 
• 3764-87-2 7α-methyl-19-nortestosterone 
• 1092-04-2 2α-Methyl-19-nor-testosteron 
• 3919-20-8 2β-Methyl-17β-hydroxy-oestr-4-en-3-on 

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.

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.

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

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.

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.