514-61-4

Basic information

• Product Name: Normethisterone
• Synonyms: NORMETHANDROLONE;NORMETHANDRONE;NORMETHISTERONE;NORETHANDRONE;17-alpha-methyl-17-beta-hydroxy-4-estren-3-one;17-beta-hydroxy-17-alpha-methyl-estr-4-en-3-on;17-beta-hydroxy-17-methylestr-4-en-3-one;17-methyl-19-nortestosterone
• CAS NO: 514-61-4
• Molecular Formula: C₁₉H₂₈O₂
• Molecular Weight: 288.42
• EINECS: 208-183-0
• Product Categories: Intermediates & Fine Chemicals;Pharmaceuticals;Steroids
• Mol File: 514-61-4.mol
• Article Data: 0

Chemical Properties

• Melting Point: 153-158°C
• Boiling Point: 370.65°C (rough estimate)
• Flash Point: 185.4 °C
• Appearance: white solid
• Density: 1.0484 (rough estimate)
• Vapor Pressure: 2.22E-09mmHg at 25°C
• Refractive Index: 1.4709 (estimate)
• Storage Temp.: Controlled Substance, -20°C Freezer
• PKA: 15.13±0.40(Predicted)
• CAS DataBase Reference: Normethisterone(CAS DataBase Reference)
• NIST Chemistry Reference: Normethisterone(514-61-4)
• EPA Substance Registry System: Normethisterone(514-61-4)

Safety Data

• Hazardous Substances Data: 514-61-4(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

Androgen. Controlled substance (anabolic steroid).

InChI:InChI=1/C19H28O2/c1-18-9-7-15-14-6-4-13(20)11-12(14)3-5-16(15)17(18)8-10-19(18,2)21/h11,14-17,21H,3-10H2,1-2H3/t14-,15+,16+,17-,18-,19-/m0/s1

Synthetic route

3-ethoxy-19-nor-3,5-androstadiene-17-one (2863-88-9) + methylmagnesium bromide (75-16-1) → normethandrolone (514-61-4)

Conditions	Yield
With hydrogenchloride

methylmagnesium bromide (75-16-1) + 3,3-ethanediyldioxy-17ξ-hydroxy-estr-5-ene-17ξ-carbonitrile (96111-40-9) → normethandrolone (514-61-4)

Conditions	Yield
With hydrogenchloride

3,3-ethanediyldioxy-17α-methyl-estr-5-en-17β-ol (5696-57-1) → normethandrolone (514-61-4)

Conditions	Yield
With acetic acid

3-methoxy-17α-methyl-estra-1,3,5(10)-trien-17β-ol → normethandrolone (514-61-4)

Conditions	Yield
With hydrogenchloride; ammonia; lithium

19-nortestosterone (434-22-0) → normethandrolone (514-61-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: CrO3 3: aqueous HCl View Scheme

estra-4-ene-3,17-dione (734-32-7) → normethandrolone (514-61-4)

Conditions	Yield
Multi-step reaction with 2 steps 2: aqueous HCl View Scheme

normethandrolone (514-61-4) → 17α-methyl-6β,17β-dihydroxyestr-4-en-3-one (1428370-33-5) + 17α-(hydroxymethyl)-11β,17β-dihydroxyestr-4-en-3-one (1428370-34-6) + 17α-methyl-2α,11β,17β-trihydroxyestr-4-en-3-one (1428370-35-7) + 17α-methyl-1β,17β-dihydroxyestr-4-en-3-one (1428370-36-8) + 17α-methyl-11β,17β-dihydroxyestr-4-en-3-one (7100-20-1) + 17α-methyl-11α,17β-dihydroxyestr-4-en-3-one (7100-20-1)

Conditions	Yield
With Macrophomina phaseolina KUCC 730 In water for 192h; Microbiological reaction;	A 0.018% B 0.008% C 0.006% D 0.045% E 0.014% F 0.0045%

normethandrolone (514-61-4) → 17α-methyl-3,17β-dihydroxyestr-1,3,5(10)-trien-6-one (1428370-37-9) + 17-methyl-estra-1,3,5(10)-triene-3,17α-diol (302-76-1) + 17α-methyl-11β,17β-dihydroxyestr-4-en-3-one (7100-20-1)

Conditions	Yield
With Gibberella fujikuroi ATCC 10704 In water; acetone for 264h; Microbiological reaction;	A 0.01% B 0.014% C n/a

normethandrolone (514-61-4) → 17α-methyl-6β,17β-dihydroxyestr-4-en-3-one (1428370-33-5) + 17α-methyl-10β,17β-dihydroxyestr-4-en-3-one (18318-25-7) + 17α-(hydroxymethyl)-17β-hydroxyestr-4-en-3-one (67473-37-4)

Conditions	Yield
With Aspergillus niger ATCC 10549 In water; acetone for 336h; Microbiological reaction;	A n/a B 0.008% C 0.012%

normethandrolone (514-61-4) → 17α-methyl-6β,10β,17β-trihydroxyestr-4-en-3-one (1428370-38-0) + 17α-methyl-11α,17β-dihydroxyestr-4-en-3-one (7100-20-1)

Conditions	Yield
With Cunninghamella echinulata ATCC 9244 In water; acetone for 288h; Microbiological reaction;	A 0.006% B n/a

normethandrolone (514-61-4) → 17-methyl-estr-5-ene-3β,17β-diol (95554-01-1)

normethandrolone (514-61-4) → 17-methyl-5α-estrane-3β,17β-diol (31658-47-6)

Conditions	Yield
With methanol; ammonia; lithium

normethandrolone (514-61-4) → 17α-methyl-11α,17β-dihydroxyestr-4-en-3-one (7100-20-1)

Conditions	Yield
mit Hilfe von Rhizopus nigricans;

normethandrolone (514-61-4) + benzoyl chloride (98-88-4) → 17β-benzoyloxy-17α-methyl-estr-4-en-3-one

normethandrolone (514-61-4) + ethylene glycol (107-21-1) → 3,3-ethanediyldioxy-5,6α-epoxy-17α-methyl-5α-estran-17β-ol (113455-03-1) + 3,3-ethanediyldioxy-5,10-epoxy-17α-methyl-5β-estran-17β-ol (113563-89-6)

Conditions	Yield
With toluene-4-sulfonic acid; benzene Behandeln des Reaktionsprodukts in Chloroform mit Monoperoxyphthalsaeure in Aether;

normethandrolone (514-61-4) + ethylene glycol (107-21-1) → 3,3-ethanediyldioxy-17α-methyl-estr-5-en-17β-ol (5696-57-1)

Conditions	Yield
With toluene-4-sulfonic acid; benzene

normethandrolone (514-61-4) + formic acid ethyl ester (109-94-4) → 17β-hydroxy-17α-methyl-3-oxo-estr-4-ene-2-carbaldehyde

Conditions	Yield
With sodium hydride; benzene

normethandrolone (514-61-4) + methyl iodide (74-88-4) → 17β-hydroxy-4,4,17α-trimethyl-estr-5-en-3-one (56053-68-0)

Conditions	Yield
With potassium tert-butylate; tert-butyl alcohol

ethyl bromide (74-96-4) + normethandrolone (514-61-4) → 5β-Ethyl-17β-hydroxy-17-methylestran-3-on (56006-61-2)

Conditions	Yield
(i) Mg, THF, (ii) /BRN= 2622263/, Cu(OAc)2; Multistep reaction;

Vinyl bromide (593-60-2) + normethandrolone (514-61-4) → 17β-Hydroxy-17-methyl-5β-vinylestran-3-on (56006-60-1)

Conditions	Yield
(i) Mg, THF, (ii) /BRN= 2622263/, Cu(OAc)2; Multistep reaction;

normethandrolone (514-61-4) → 17,17-Dimethyl-gona-4,13-dien-3-on (153-23-1)

Conditions	Yield
With hydrogenchloride In acetic acid

methyl magnesium iodide (917-64-6) + normethandrolone (514-61-4) → 17β-hydroxy-5,17-dimethyl-19-nor-5β,9α,10β-androstan-3-one (56085-15-5)

Conditions	Yield
With tetrahydrofuran; diethyl ether; copper(l) chloride

methyl magnesium iodide (917-64-6) + normethandrolone (514-61-4) → 3,17α-Dimethyl-oestradien-(3,5)-ol-(17β)

Conditions	Yield
With tetrahydrofuran; diethyl ether; copper(l) chloride

normethandrolone (514-61-4) → (8R,9S,10R,13S,14S,17S)-13,17-Dimethyl-2,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-ol

Conditions	Yield
(i) LiAlH4, THF, (ii) aq. HCl, acetone; Multistep reaction;

normethandrolone (514-61-4) + phenyllithium (591-51-5) → (8R,9S,10R,13S,14S,17S)-13,17-Dimethyl-3-phenyl-2,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-ol

Conditions	Yield
(i) Et2O, THF, (ii) aq. HCl, acetone; Multistep reaction;

normethandrolone (514-61-4) → 4,4,17-trimethyl-5α-estrane-3β,17β-diol (97016-87-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: potassium tert-butylate; tert-butyl alcohol 3: NaBH4; aqueous dioxane View Scheme

normethandrolone (514-61-4) → 17β-hydroxy-17α-methyl-estr-5-en-3-one (95801-37-9)

Conditions	Yield
Multi-step reaction with 2 steps 2: acetone; CrO3; H2SO4 View Scheme

normethandrolone (514-61-4) → 4,4,17-trimethyl-estr-5-ene-3β,17β-diol (88870-36-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium tert-butylate; tert-butyl alcohol 2: NaBH4; aqueous dioxane View Scheme

normethandrolone (514-61-4) → 17β-hydroxy-4,4,17α-trimethyl-5α-estran-3-one (64006-29-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium tert-butylate; tert-butyl alcohol View Scheme

Upstream product

• 734-32-7 estra-4-ene-3,17-dione 
• 434-22-0 19-nortestosterone 
• 5696-57-1 3,3-ethanediyldioxy-17α-methyl-estr-5-en-17β-ol 
• 75-16-1 methylmagnesium bromide 
• 96111-40-9 3,3-ethanediyldioxy-17ξ-hydroxy-estr-5-ene-17ξ-carbonitrile 
• 2863-88-9 3-ethoxy-19-nor-3,5-androstadiene-17-one 

Downstream Products

• 95554-01-1 17-Methyl-oestr-5-en-3β,17β-diol 
• 1428370-37-9 17α-methyl-3,17β-dihydroxyestr-1,3,5(10)-trien-6-one 
• 302-76-1 17-methyl-estra-1,3,5(10)-triene-3,17α-diol 
• 7100-20-1 17α-methyl-11β,17β-dihydroxyestr-4-en-3-one 
• 153-23-1 17,17-Dimethyl-gona-4,13-dien-3-on