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(-)-N-METHYLEPHEDRINE

(-)-N-METHYLEPHEDRINE Structure
(-)-N-METHYLEPHEDRINE structure
CAS No.
552-79-4
Chemical Name:
(-)-N-METHYLEPHEDRINE
Synonyms
METHYLEPHEDRINE;L-N-METHYLEPHEDRINE;(-)-1R,2S N-METHYLEPHEDRINE;2-(Dimethylamino)-1-phenyl-1-propanol;(-)-(1R,2S)-2-DIMETHYLAMINO-1-PHENYL-1-PROPANOL;(-)-ALPHA-[1-(DIMETHYLAMINO)ETHYL]BENZENEMETHANOL;Dimethyl-ephedrine;(-)-Methylephedrine;N-Methyl-L-ephedrine;(-)-N-METHYLEPHEDRINE
CBNumber:
CB7495234
Molecular Formula:
C11H17NO
Molecular Weight:
179.26
MDL Number:
MFCD00004504
MOL File:
552-79-4.mol
Last updated:2023-05-04 17:34:39

(-)-N-METHYLEPHEDRINE Properties

Melting point 86-88 °C(lit.)
Boiling point 311.8°C (rough estimate)
Density 1.0020 (rough estimate)
refractive index 1.5065 (estimate)
Flash point 9℃
storage temp. Refrigerator (+4°C)
pka pKa 9.257(H2O,t =25,I=0.00) (Uncertain)
form Powder
Sensitive Moisture Sensitive
Merck 14,6068
CAS DataBase Reference 552-79-4(CAS DataBase Reference)
FDA UNII 60VH42A1KJ

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictogramsGHS hazard pictogramsGHS hazard pictogramsGHS hazard pictograms
GHS02,GHS06,GHS08,GHS07
Signal word  Danger
Hazard statements  H225-H301+H311+H331-H370-H302-H315-H319-H335
Precautionary statements  P261-P280a-P304+P340-P305+P351+P338-P405-P501a-P210-P260-P280-P301+P310-P311
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
F  3
HazardClass  6.1(b)
PackingGroup  III

(-)-N-METHYLEPHEDRINE Chemical Properties,Uses,Production

Description

The 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 Properties

White crystals or adhering crystalline powder

Uses

adrenergic agonist, analeptic

Uses

Used in conjunction with LiAlH4 for chiral reductions

Definition

ChEBI: (1R,2S)-2-(dimethylamino)-1-phenyl-1-propanol is an alkylbenzene.

Purification Methods

N-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.]

References

Smith., 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 synthesis

50-00-0
299-42-3
552-79-4
Synthesis of (-)-N-METHYLEPHEDRINE from Formaldehyde and Ephedrine

(-)-N-METHYLEPHEDRINE Preparation Products And Raw materials

Raw materials

Pseudoephedrine EPHEDRINE HYDROCHLORIDE - * DRUG PRECURSOR Methanol Carbon dioxide Formaldehyde

Preparation Products

Ephedrine

(-)-N-METHYLEPHEDRINE Spectrum

(-)-N-METHYLEPHEDRINE(552-79-4)MS(-)-N-METHYLEPHEDRINE(552-79-4)1HNMR(-)-N-METHYLEPHEDRINE(552-79-4)IR1(-)-N-METHYLEPHEDRINE(552-79-4)IR2(-)-N-METHYLEPHEDRINE(552-79-4)Raman

552-79-4((-)-N-METHYLEPHEDRINE)Related Search:

Trecadrine (1S,2R)-N-TOSYLEPHEDRINE (+)-Bicuculline (1R,2S)-2-DI-N-BUTYLAMINO-1-PHENYL-1-PROPANOL tert-Butyl (2R,3S)-(-)-6-oxo-2,3-diphenyl-4-morpholinecarboxylate
Benzyl (2R,3S)-(-)-6-oxo-2,3-diphenyl-4-morpholinecarboxylate (S)-(+)-2-[HYDROXY(DIPHENYL)METHYL]-1-METHYLPYRROLIDINE L-N-METHYLEPHEDRINE HYDROCHLORIDE, 99 (-)-BETA-HYDRASTINE Ipenoxazone
(-)-N-METHYLEPHEDRINE (-)-BICUCULLINE METHOBROMIDE (-)-N-DODECYL-N-METHYLEPHEDRINIUM BROMIDE dl-Methylephedrine HCl ,dl-methylephedrine hydrochloride L-N-METHYLEPHEDRINE HYDROCHLORIDE,METHYLEPHEDRINE HCL,(IR,2S)-I-N-Methylephedrine HCL
(+)-N-METHYLEPHEDRINE 1-Phenyl-1-propanol Ephedrine

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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 (IR,2S)-I-N-Methylephedrine Base METHYLEPHEDRINE, (-)-1R,2S SNAPN 1.0mg/mL(SH) N-Methylephedrine (base and/or unspecified salts) (-)-N-Methylephedrine, 98+% (-)-N-Methylephedrine, (-)-(1R,2S)-2-Dimethylamino-1-phenylpropanol, [R-(R*,S*)]-α-[1-(Dimethylamino)ethyl]benzenemethanol (-)-N-Methylephedrine,99% [R-(R,S)]-α-[1-(Dimethylamino)ethyl]benzenemethanol Methanol(Test Methylephedrine, 1.0 mg/mL) N-METHYL (-)EPHEDRINE [1R,2S] Methylephedrine solution (1Rs,2Rs)-2-dimethylamino-1-phenylpropan-1-ol -[1-(Dimethylamino)ethyl]benzenemethanol [R,(-)]-α-[(S)-1-(Dimethylamino)ethyl]benzyl alcohol Dimethyl-ephedrine METHYLEPHEDRINE, (-)-1R,2S- METHYLEPHEDRINE, (-)-1R,2S N- Benzenemethanol, alpha-[1-(dimethylamino)ethyl]-, [R-(R*,S*)]- Erythro-alpha-[1-(dimethylamino)ethyl]benzyl alcohol N,N-Dimethylnorephedrine N,N-Dimethylnorephedrine2-dimethylamino-1-phenylpropanol [R-(R*,S*)]-ALPHA-[1-(DIMETHYLAMINO)ETHYL]BENZENEMETHANOL (-)-N-METHYLEPHEDRINE (1R,2S)-(-)-N--Methylephedrine solution Cinchocaine Solution, 100ppm (-)-N-METHYLEPHEDRINE USP/EP/BP (-)-Methylephedrine (-)-1R,2S N-METHYLEPHEDRINE (-)-(1R,2S)-2-DIMETHYLAMINO-1-PHENYL-1-PROPANOL 2-(Dimethylamino)-1-phenyl-1-propanol L-N-METHYLEPHEDRINE (-)-ALPHA-[1-(DIMETHYLAMINO)ETHYL]BENZENEMETHANOL METHYLEPHEDRINE Methylephedrine ((1R,2S)-Methylephedrine) 552-79-4 C6H5CHOHCHCH3NCH32 Asymmetric Synthesis Chiral Auxiliaries Ephedrine Derivatives Pharmaceutical Raw Materials