ChemicalBook CAS DataBase List 492-41-1

492-41-1

Name	L-(-)-Ephedrine
CAS	492-41-1
EINECS(EC#)	207-755-7
Molecular Formula	C10H15NO
MDL Number	MFCD00066044
Molecular Weight	165.23
MOL File	492-41-1.mol

Synonyms

(1R,2S)-(-)-2-AMINO-1-PHENYL-1-PROPANOL (1R,2S)-2-AMINO-1-PHENYL-1-PROPANOL (1R,2S)-2-AMINO-1-PHENYLPROPAN-1-OL (-)-1R,2S-NOREPHEDRINE (1R,2S)-(-)-NOREPHEDRINE (1R,2S)-(-)-NOREPHEDRINE, L-(-)-NOREPHEDRINE (1R,2S)-(-)-PHENYLPROPANOLAMINE 2-AMINO-1-PHENYL-1-PROPANOL AURORA KA-7791 AURORA KA-7792 DL-NOREPHEDRINE L-(-)-NOREPHEDRINE NOREPHEDRINE, (-)-1R,2S- (-)-benzylalcoho (-)-norephedrin (-)-Norephedrine 1-Propanol, 2-amino-1-phenyl- alpha-(1-aminoethyl)-,(r-(r*,s*))-benzenemethano alpha-(1-aminoethyl)-,[theta-(theta,s)]-benzenemethano Benzenemethanol, alpha-(1-aminoethyl)-, [R-(R*,S*)]-

Chemical Properties

Appearance	white powder
Melting point	51-53 °C(lit.)
alpha	-41 º (c=7, 1M HCl)
Boiling point	273.23°C (rough estimate)
density	1.0406 (rough estimate)
refractive index	1.5380 (estimate)
Fp	>230 °F
storage temp.	2-8°C
form	A solid
pka	9.958(at 10℃)
Stability:	Stable. Incompatible with strong oxidizing agents. May discolour on exposure to light.
Optical Rotation	[α]20/D -41°, c =7 in 1 M HCl
InChI	1S/C9H13NO/c1-7(10)9(11)8-5-3-2-4-6-8/h2-7,9,11H,10H2,1H3/t7-,9-/m0/s1
InChIKey	DLNKOYKMWOXYQA-CBAPKCEASA-N
SMILES	C[C@H](N)[C@H](O)c1ccccc1
CAS DataBase Reference	492-41-1(CAS DataBase Reference)
NIST Chemistry Reference	Phenylpropanolamine(492-41-1)
EPA Substance Registry System	492-41-1(EPA Substance)

Safety Data

Hazard Codes	Xn
Risk Statements	R22:Harmful if swallowed. R36/37/38:Irritating to eyes, respiratory system and skin . less more
Safety Statements	S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . less more
WGK Germany	3
RTECS	RC2275000
F	3-8-10
Hazard Note	Harmful
TSCA	TSCA listed
REACH Registrations	Active
Storage Class	11 - Combustible Solids
Hazard Classifications	Acute Tox. 4 Oral Eye Irrit. 2 Skin Irrit. 2 STOT SE 3
Safety Profile	A human poison by ingestion. Poison experimentally by intravenous, subcutaneous, and intraperitoneal routes. Moderately toxic by an unspecified route. Human systemic effects by ingestion: sleep, increased pulse rate without blood pressure decrease, and chronic pulmonary edema or congestion, convulsions, headache, and blood pressure elevation. Used in production of drugs of abuse. When heated to decomposition it emits toxic fumes of NOx. less more
Toxicity	LD50 orl-rat: 1538 mg/kg BCFAAI 109,132,70 less more

Hazard Information

Description

This alkaloid was first isolated by Kanao from the Chinese drug 'Ma-Huang' (Ephedra sinica Stapf.) and later by Wolfes from E. helvetica C. A. Meyer and E. distachya Linn. It forms a crystalline mass and has [α] ²⁰ _D - 14.56° (EtOH). Several crystalline salts and derivatives are known: the hydrochloride has m.p. 171-2°C; [α] ²⁰ _D- 33.27° (H20); the sulphate dihydrate, m.p. 285-6°C (dry, dec.); [α] ²⁸ _D- 31.99° (H20); the aurichloride, m.p. 188°C; platinichloride, m.p. 221°C (dec.); (-)-hydrogen tartrate, m.p. about 160° after sintering at 130°C; oxalate, m.p. 245°C (dec.) and the p-nitrobenzoyl derivative, m.p. 175-6°C; [α] ²⁸ _D- 49.58° (CHCI3).
The (+)-form has m.p. 52°C; [α] ²⁷ _D + 14.76° (EtOH), yielding a hydro_x0002_chloride, m.p. 171-2°C; [α] ²⁷ _D + 33.4° (EtOH); sulphate dihydrate, m.p. 285- 6°C (dry, dec.); [α] ²⁷ _D+ 31.51 0 C (H20); aurichloride, m.p. 188°C (dec.) and platinichloride, m.p. 221.5°C (dec.). The (±)-form crystallizes as colourless plates from Et20, m.p. 104-5°C and also furnishes a series of crystalline salts and derivatives.

Chemical Properties

white powder

Uses

A metabolite of Phenmetrazine.

Definition

ChEBI: (-)-norephedrine is an amphetamine that is propylbenzene substituted by a hydroxy group at position 1 and by an amino group at position 2 (the 1R,2S-stereoisomer). It is a plant alkaloid. It has a role as a plant metabolite. It is a member of amphetamines and a phenethylamine alkaloid.

References

Kanao., Ber., 63,95 (1930) Wolfes., Arch. Pharrn., 268,87 (1930) Hey., J. Chern. Soc., 1232 (1930) Akabori, Momotani., J. Chern. Soc., Japan, 64, 608 (1943) Hoover, Hass., J. Org. Chern., 12,506 (1947)

Spectrum Detail

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