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Name	Normethisterone	EINECS	208-183-0
CAS No.	514-61-4	Density	1.12 g/cm³
PSA	37.30000	LogP	3.87920
Solubility	N/A	Melting Point	153-158 °C
Formula	C₁₉H₂₈O₂	Boiling Point	434.6 °C at 760 mmHg
Molecular Weight	288.43	Flash Point	185.4 °C
Transport Information	N/A	Appearance	white solid
Safety		Risk Codes	R20/21; R65
Molecular Structure		Hazard Symbols	N/A
Synonyms	Estr-4-en-3-one,17b-hydroxy-17-methyl- (8CI);17-Methyl-19-nortestosterone;17a-Methyl-17b-hydroxy-4-estrene-3-one;17a-Methyl-19-nortestosterone;17a-Methyl-3-oxo-4-estren-17b-ol;17a-Methylestra-4-en-17-ol-3-one;17b-Hydroxy-17a-methylestr-4-en-3-one;19-Normethisterone;Lutenin;Methylnortestosterone;NSC 10039;Normetandrone;Orgasteron;RU 598;

Normethisterone Synthetic route

: 2863-88-9
3-ethoxy-19-nor-3,5-androstadiene-17-one

: 75-16-1
methylmagnesium bromide

: 514-61-4
normethandrolone

Conditions

Conditions	Yield
With hydrogenchloride

: 75-16-1
methylmagnesium bromide

: 96111-40-9
3,3-ethanediyldioxy-17ξ-hydroxy-estr-5-ene-17ξ-carbonitrile

: 514-61-4
normethandrolone

Conditions

Conditions	Yield
With hydrogenchloride

: 5696-57-1
3,3-ethanediyldioxy-17α-methyl-estr-5-en-17β-ol

: 514-61-4
normethandrolone

Conditions

Conditions	Yield
With acetic acid

3-methoxy-17α-methyl-estra-1,3,5(10)-trien-17β-ol: 3-methoxy-17α-methyl-estra-1,3,5(10)-trien-17β-ol

: 514-61-4
normethandrolone

Conditions

Conditions	Yield
With hydrogenchloride; ammonia; lithium

: 434-22-0
19-nortestosterone

: 514-61-4
normethandrolone

Conditions

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

: 734-32-7
estra-4-ene-3,17-dione

: 514-61-4
normethandrolone

Conditions

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

: 514-61-4
normethandrolone

A: 1428370-33-5
17α-methyl-6β,17β-dihydroxyestr-4-en-3-one

B: 1428370-34-6
17α-(hydroxymethyl)-11β,17β-dihydroxyestr-4-en-3-one

C: 1428370-35-7
17α-methyl-2α,11β,17β-trihydroxyestr-4-en-3-one

D: 1428370-36-8
17α-methyl-1β,17β-dihydroxyestr-4-en-3-one

E: 7100-20-1
17α-methyl-11β,17β-dihydroxyestr-4-en-3-one

F: 7100-20-1
17α-methyl-11α,17β-dihydroxyestr-4-en-3-one

Conditions

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%

...Expand

: 514-61-4
normethandrolone

A: 1428370-37-9
17α-methyl-3,17β-dihydroxyestr-1,3,5(10)-trien-6-one

B: 302-76-1
17-methyl-estra-1,3,5(10)-triene-3,17α-diol

C: 7100-20-1
17α-methyl-11β,17β-dihydroxyestr-4-en-3-one

Conditions

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

: 514-61-4
normethandrolone

A: 1428370-33-5
17α-methyl-6β,17β-dihydroxyestr-4-en-3-one

B: 18318-25-7
17α-methyl-10β,17β-dihydroxyestr-4-en-3-one

C: 67473-37-4
17α-(hydroxymethyl)-17β-hydroxyestr-4-en-3-one

Conditions

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

: 514-61-4
normethandrolone

A: 1428370-38-0
17α-methyl-6β,10β,17β-trihydroxyestr-4-en-3-one

B: 7100-20-1
17α-methyl-11α,17β-dihydroxyestr-4-en-3-one

Conditions

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

Normethisterone Chemical Properties

Product Name: Metalutin (CAS NO.514-61-4)

Molecular Formula: C₁₉H₂₈O₂
Molecular Weight: 288.42g/mol
Mol File: 514-61-4.mol
Einecs: 208-183-0
Melting Point: 153-158°C
Boiling point: 434.6 °C at 760 mmHg
Flash Point: 185.4 °C
Density: 1.12 g/cm³
Surface Tension: 44.4 dyne/cm
Enthalpy of Vaporization: 79.75 kJ/mol
Vapour Pressure: 2.22E-09 mmHg at 25°C
XLogP3-AA: 2.8
H-Bond Donor: 1
H-Bond Acceptor: 2

Normethisterone Toxicity Data With Reference

1.		orl-wmn TDLo:18 mg/kg (12-24W preg):TER		BRGOAY Bulletin de la Societa Royale Belge de Gynecologie et dObstetrique. 28 (1958),137.
2.		orl-rbt TDLo:200 µg/kg (female 1D pre):REP		85GRAA The Control of Fertility Pincus, G.,New York, NY.: Academic Press,1965,57.

Normethisterone Safety Profile

Human teratogenic effects by ingestion: extra embryonic structures and developmental abnormalities of the urogenital system. An experimental teratogen. Experimental reproductive effects. When heated to decomposition it emits acrid smoke and irritating fumes. See also TESTOSTERONE.

Normethisterone Specification

Metalutin ,its CAS NO. is 514-61-4,the synonyms is 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 .

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