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HomeProduct name list(-)-N-METHYLEPHEDRINE

(-)-N-METHYLEPHEDRINE

Synonym(s):(−)-(1R,2S)-2-Dimethylamino-1-phenylpropanol;(−)-N-Methylephedrine;[R-(R*,S*)]-α-[1-(Dimethylamino)ethyl]benzenemethanol;Ephedra

  • CAS NO.:552-79-4
  • Empirical Formula: C11H17NO
  • Molecular Weight: 179.26
  • MDL number: MFCD00004504
  • EINECS: 209-022-7
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2023-05-04 17:34:39
(-)-N-METHYLEPHEDRINE Structural

What is (-)-N-METHYLEPHEDRINE?

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

The Uses of (-)-N-METHYLEPHEDRINE

adrenergic agonist, analeptic

The Uses of (-)-N-METHYLEPHEDRINE

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)

Properties of (-)-N-METHYLEPHEDRINE

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)
form  Powder
pka pKa 9.257(H2O,t =25,I=0.00) (Uncertain)
Sensitive  Moisture Sensitive
Merck  14,6068
CAS DataBase Reference 552-79-4(CAS DataBase Reference)

Safety information for (-)-N-METHYLEPHEDRINE

Signal word Danger
Pictogram(s)
ghs
Flame
Flammables
GHS02
ghs
Skull and Crossbones
Acute Toxicity
GHS06
ghs
Exclamation Mark
Irritant
GHS07
ghs
Health Hazard
GHS08
GHS Hazard Statements H225:Flammable liquids
H302:Acute toxicity,oral
H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
H370:Specific target organ toxicity, single exposure
Precautionary Statement Codes P210:Keep away from heat/sparks/open flames/hot surfaces. — No smoking.
P260:Do not breathe dust/fume/gas/mist/vapours/spray.
P261:Avoid breathing dust/fume/gas/mist/vapours/spray.
P280:Wear protective gloves/protective clothing/eye protection/face protection.
P311:Call a POISON CENTER or doctor/physician.
P301+P310:IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P304+P340:IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P405:Store locked up.

Computed Descriptors for (-)-N-METHYLEPHEDRINE

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