Ephedrine
Legality: DEA Listed Chemicals
Production of this substance may be illegal in some jurisdictions under certain circumstances.
21CFR1310.02 a & b
In 1995/6, two lists were created "List I" and "List II", for which commercial manufacturers and distributors must register, and for which possession with the intent to manufacture illegal substances (such as methamphetamine, ecstasy, etc) is illegal. On these a few dozen "precursor" compounds commonly used in the manufacture of illegal drugs. [1] [2]
Bottom line: Do not produce this chemical without checking to make sure that you may do so legally.
| Chemical formula | C13H21NO3 |
|---|---|
| OTP appearance | solid |
| Molar Mass(g/mol) | 165.23 |
| Density(g/cc) | 1.124 |
| Melting Point(°C) | 37-39 |
| Boiling Point(°C) | 255 |
| NFPA 704 |  0
0
0
|
| Chemical formula | C13H21NO3 |
|---|---|
| OTP appearance | solid |
| Molar Mass(g/mol) | 165.23 |
| Density(g/cc) | 1.124 |
| Melting Point(°C) | 118-119 |
| NFPA 704 | 0
0
0
|
Uses
Primary
- WHO LEM
Natural occurrence
- Ephendrine occurs naturally
- Pseudoephedrine occurs naturally.
Hazards
Production
Extraction
from Ephedra sinica
From ephedra sinica
- Dry and powder plant
- Extract with benzene and potassium carbonate
- Filter
- Discard residue
- Add hydrochloric acid
- Filter
- Discard residue
- Add potassium carbonate to filtrate
- Add trichloromethane
- Mix thoroughly
- Discard aqueous layer
- Add sodium sulfate or other drying agent to filtrate
- Mix thoroughly
- Filter
- Discard residue
- Distil ether
- Estimate yield 2.6g from 1kg of dried plant powder
Synthesis
Purification
- Dissolve mixed bases in ethanol
- Neutralize with a hydrochloric acid / ethanol mixture
- Allow to stand
- Filter
- Optionally retain filtrate - it may contain additional product
- Wash residue with ethanol and diethyl ether
- Retain residue
Separation
ephedrine from pseudoephedrine
- Separating ephedrine and pseudoephedrine by aqueous solubility of their oxalates
- Mix base with warm aqueous solution of oxalic acid (or sodium oxalate if in hydrochloride form)
- Chill
- Filter
- Residue is ephedrine oxalate
- Add calcium chloride to filtrate
- Filter
- Decompose filtrate (calcium oxalate)
- Dry filtrate (contains salt and pseudoephedrine)
further
The separation of the six natural ephedra bases has been described by Kanao.[3] l-Ephedrine was first separated as hydrochloride, then pseudoephedrine as the free base, l-methylephedrine as the oxalate, d-methyl-pseudoephedrine as the d-bitartrate and finally nor-d-pseudo-ephedrine, from alcohol, as the sulfate. Norephedrine, which crystallizes together with nor-d-pseudo-ephedrine was separated in the form of its l-bitartrate.
Conversion
- Converting ephedrine and pseudoephedrine back and forth
See Also
- Chou, T.Q. (1926) "The Preparation and Properties of Ephedrine and Its Salts" (local copy)
Journal of Biologivcal Chemistry 1(70); pp109-115.
link courtesy Journal of Biological Chemistry. - Ephedrine And Its Salts, Isolation And Properties
- Chen, K.K.; Kao, C.H. (1926) "Ephedrine and Pseudoephedrine, their Isolation, Constitution, Isomerism, Properties, Derivatives and Synthesis. (with a Bibliography)".
Journal of Pharmaceutical Sciences 15(8); pp625–639.
References
- ↑ "Emphasizing the "Control" in controlled substances"
United States Drug Enforcement Agency
link last accessed 11 September 2012. - ↑ "Controlled Substances Act; Title 21; Chapter 13; Subchapter I"
United States Food & Drug Administration
link last accessed 11 September 2012. - ↑ Kanao, S. (1930) "l-nor-ephedrine (About the components of Chinese drug "Ma Huang", VII. msgs.)"
Berichte der Deutschen Chemischen Gesellschaft(95)
link courtesy European Journal of Inorganic Chemistry.