ChemicalBook > CAS DataBase List > (-)-N-METHYLEPHEDRINE

(-)-N-METHYLEPHEDRINE

Product Name
(-)-N-METHYLEPHEDRINE
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
Formula Weight
179.26
MOL File
552-79-4.mol
More
Less

(-)-N-METHYLEPHEDRINE Property

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)
More
Less

Safety

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
More
Less

Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H225Highly Flammable liquid and vapour

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

H370Causes damage to organs

Precautionary statements

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P260Do not breathe dust/fume/gas/mist/vapours/spray.

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P310IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P311Call a POISON CENTER or doctor/physician.

P405Store locked up.

More
Less

N-Bromosuccinimide Price

Sigma-Aldrich
Product number
235210
Product name
(1R,2S)-(−)-N-Methylephedrine
Purity
99%
Packaging
5G
Price
$182
Updated
2024/03/01
Sigma-Aldrich
Product number
M-129
Product name
(1R,2S)-(-)-N--Methylephedrine solution
Purity
1.0?mg/mL in methanol, ampule of 1?mL, certified reference material, Cerilliant?
Packaging
1mL
Price
$44.8
Updated
2022/05/15
Alfa Aesar
Product number
041570
Product name
(-)-N-Methylephedrine
Purity
98+%
Packaging
1g
Price
$33.6
Updated
2022/04/27
More
Less

(-)-N-METHYLEPHEDRINE Chemical Properties,Usage,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 Preparation Products And Raw materials

Raw materials

Pseudoephedrine EPHEDRINE HYDROCHLORIDE - * DRUG PRECURSOR

Preparation Products

Ephedrine
More
Less

(-)-N-METHYLEPHEDRINE Suppliers

Global 0

552-79-4, (-)-N-METHYLEPHEDRINERelated 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

  • (1R,2S)-(-)-N--Methylephedrine solution
  • 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)-(-)-N-METHYLEPHEDRINE
  • (-)-1R,2S-METHYLEPHEDRINE
  • (-)-(1R,2S)-2-DIMETHYLAMINO-1-PHENYL-1-PROPANOL
  • (-)-(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-
  • 2-(Dimethylamino)-1-phenyl-1-propanol
  • Benzenemethanol, alpha-[1-(dimethylamino)ethyl]-, [R-(R*,S*)]-
  • Erythro-alpha-[1-(dimethylamino)ethyl]benzyl alcohol
  • N,N-Dimethylnorephedrine
  • N,N-Dimethylnorephedrine2-dimethylamino-1-phenylpropanol
  • L-N-METHYLEPHEDRINE
  • (-)-ALPHA-[1-(DIMETHYLAMINO)ETHYL]BENZENEMETHANOL
  • METHYLEPHEDRINE
  • Cinchocaine Solution, 100ppm
  • [R-(R*,S*)]-ALPHA-[1-(DIMETHYLAMINO)ETHYL]BENZENEMETHANOL
  • (-)-N-METHYLEPHEDRINE
  • (-)-N-METHYLEPHEDRINE USP/EP/BP
  • (-)-Methylephedrine
  • Methylephedrine ((1R,2S)-Methylephedrine)
  • 552-79-4
  • C6H5CHOHCHCH3NCH32
  • Asymmetric Synthesis
  • Chiral Auxiliaries
  • Ephedrine Derivatives
  • Pharmaceutical Raw Materials