(-)-N-METHYLEPHEDRINE

(-)-N-METHYLEPHEDRINE Basic information
Product Name:(-)-N-METHYLEPHEDRINE
Synonyms:METHYLESCULETIN, 4-(RG);(1R,2S)-3-Dimethylamino-1-phenyl-1-propanol;Benzenemethanol, α-[(1S)-1-(dimethylamino)ethyl]-, (αR)-;Benzenemethanol, α-[1-(dimethylamino)ethyl]-, [R-(R*,S*)]-;N-Methyl-L-ephedrine;(1R,2S)-(-)-N-METHYLEPHEDRINE;(-)-1R,2S-METHYLEPHEDRINE;(-)-(1R,2S)-2-DIMETHYLAMINO-1-PHENYLPROPANOL
CAS:552-79-4
MF:C11H17NO
MW:179.26
EINECS:209-022-7
Product Categories:Pharmaceutical Raw Materials
Mol File:552-79-4.mol
(-)-N-METHYLEPHEDRINE Structure
(-)-N-METHYLEPHEDRINE Chemical Properties
Melting point 86-88 °C(lit.)
Boiling point 311.8°C (rough estimate)
density 1.0020 (rough estimate)
refractive index 1.5065 (estimate)
Fp 9℃
storage temp. Refrigerator (+4°C)
pkapKa 9.257(H2O,t =25,I=0.00) (Uncertain)
form Powder
Sensitive Moisture Sensitive
Merck 14,6068
CAS DataBase Reference552-79-4(CAS DataBase Reference)
Safety Information
Hazard Codes Xi,T,F
Risk Statements 36/37/38-39/23/24/25-23/24/25-11
Safety Statements 26-36-45-36/37-16-7
RIDADR 1544
WGK Germany 3
3
HazardClass 6.1(b)
PackingGroup III
MSDS Information
ProviderLanguage
ACROS English
SigmaAldrich English
ALFA English
(-)-N-METHYLEPHEDRINE Usage And Synthesis
DescriptionThe Chinese plant 'Ma-Huang' contains this alkaloid, first isolated by Smith. According to Read, the name 'Ma-Huang' is the name for various Ephedra species but the material principally used in China is E. sinica Stapf. (Syn. E. j7ava Porter Smith, E. Mahuang Liu). It has subsequently been discovered in European species, notably E. helvetica C. A. Meyer and E. distachya Linn. The alkaloid crystallizes in stout, colourless needles and has [α]D - 29.2° (MeOH). It yields several crystalline salts and derivatives: hydrochloride, m.p. 188-9°C; [α]20D - 29.8° (H20); oxalate, m.p. 187°C; aurichloride, m.p. 128-9°C; picrate, m.p. 144°C and the methiodide, m.p. 212-3°C; [α]D - 21.8° (H20).
Chemical PropertiesWhite crystals or adhering crystalline powder
Usesadrenergic agonist, analeptic
UsesUsed in conjunction with LiAlH4 for chiral reductions
DefinitionChEBI: (1R,2S)-2-(dimethylamino)-1-phenyl-1-propanol is an alkylbenzene.
Purification MethodsN-Methylephedrine has been recrystallised from Et2O, pet ether, of aqueous EtOH or aqueous MeOH and has been distilled under reduced pressure. [Smith J Chem Soc 2056 1927, Tanaka & Sugawa Yakugaku Zasshi (J Pharm Soc Japan) 72 1548 1952 (Chem Abstr 47 8682 1953), Takamatsu Yakugaku Zasshi (J Pharm Soc Japan) 76 1227 1956, Chem Abstr 51 4304 1957.] The hydrochloride has m 192-193o and [] D (c 5,H2O)[Prelog & Hüfliger Helv Chim Acta 33 2021 1950].20+30o [Beilstein 13 IV 1884.]
ReferencesSmith., J. Chern. Soc., 2056 (1927)
Smith., ibid, 51 (1928)
Smith., ibid, 2755 (1929)
Wolfes., Arch. Pharrn., 268,327 (1930)
Preparation:
Nagai., J. Pharrn. Soc., Japan, No. 120, 109 (1892)
Nagai, Kanao., ibid, 48, 145 (1928)
(-)-N-METHYLEPHEDRINE Preparation Products And Raw materials
Raw materialsPseudoephedrine-->EPHEDRINE HYDROCHLORIDE - * DRUG PRECURSOR-->Methanol-->CARBON DIOXIDE-->Formaldehyde
Preparation ProductsEphedrine
Trecadrine (-)-ERYTHRO-N, N-DIETHYLNOREPHEDRINE HYDROCHLORIDE (1R,2S)-2-DI-N-BUTYLAMINO-1-PHENYL-1-PROPANOL N-PROPIONYL-(4S,5R)-4-METHYL- 5-PHENYL-2-OXAZOLIDINONE (S)-(-)N-CARBOMETHOXY-ALPHA,ALPHA-DIPHENYL -2-PYRROLIDINEMETHANOL,98% (-)-BICUCULLINE METHCHLORIDE, 1(S),9(R) tert-Butyl (2R,3S)-(-)-6-oxo-2,3-diphenyl-4-morpholinecarboxylate (S)-3-ACETYL-4-ISOPROPYL-5,5-DIPHENYLOXAZOLIDINE-2-THIONE N-ACETYL-(4S,5R)-4-METHYL 5-PHENYL-2-OXAZOLIDINONE (-)-BICUCULLINE METHIODIDE (+)-Bicuculline (1S,2R)-N-TOSYLEPHEDRINE SIBIRICINE N-CROTONYL-(4S,5R)-4-METHYL 5-PHENYL-2-OXAZOLIDINONE BICUCULLINE METHYLCHLORIDE (-), [METHYL-3H] BICUCULLINE METHYLCHLORIDE (-), [METHYL-14C] (-)-N-BENZYL-N-METHYLEPHEDRINIUM BROMIDE (S)-(+)-2-PIPERIDINO-1,1,2-TRIPHENYLETHANOL

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