(-)-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
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) |
Flame Flammables GHS02 Skull and Crossbones Acute Toxicity GHS06 Exclamation Mark Irritant GHS07 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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