Norephedrine
Structural formula | ||||||||||||||||||||||
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Structural formula of L- norephedrine | ||||||||||||||||||||||
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Non-proprietary name | Phenylpropanolamine | |||||||||||||||||||||
other names |
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Molecular formula | C 9 H 13 NO | |||||||||||||||||||||
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Molar mass | 151.21 g mol −1 | |||||||||||||||||||||
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As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . |
Norephedrine or phenylpropanolamine ( INN ) is a sympathomimetic that belongs to the group of amphetamines . It is particularly very similar to ephedrine , both chemically and in its effect.
Isomerism
Phenylpropanolamine has two stereocenters , hence there are a total of four stereoisomers of the compound. The (1 R , 2 S ) isomer is called L - or (-) - norephedrine . The (1 S , 2 S ) isomer is called cathine ("pseudonorephedrine"). The other two isomers [(1 S , 2 R ) - and (1 R , 2 R ) -phenylpropanolamine] are irrelevant.
The racemate of (1 R , 2 S ) - and (1 S , 2 R ) -phenylpropanolamine [(±) -Norephedrine] or its hydrochloride is used in finished medicinal products .
Isomers of phenylpropanolamine | ||||
Surname | (1 R , 2 S ) -phenylpropanolamine | (1 S , 2 R ) - (+) - Phenylpropanolamine | (1 S , 2 S ) - (+) - phenylpropanolamine | (1 R , 2 R ) -phenylpropanolamine |
other names |
L- norephedrine (-) - Norephedrine |
D -norephedrine (+) - norephedrine |
(+) - norpseudoephedrine |
(-) - norpseudoephedrine |
Structural formula | ||||
CAS number | 492-41-1 | 37577-28-9 | 492-39-7 | 37577-07-4 |
14838-15-4 [(±) -Norephedrine] | 36393-56-3 [(±) -Norspeudoephedrine] | |||
48115-38-4 (unspec.) | ||||
EC number | 207-755-7 | 628-077-1 | 207-754-1 | 636-436-9 |
238-900-2 [(±) -Norephedrine] | 253-014-6 [(±) -Norspeudoephedrine] | |||
ECHA info card | 100.007.051 | 100.156.379 | 100.007.050 | 100.164.234 |
100,035,349 [(±) -Norephedrine] | 100,048,179 [(±) -Norspeudoephedrine] | |||
PubChem | 10297 | 26934 | 441457 | 162265 |
4786 (unspec.) | ||||
Wikidata | Q26840801 | Q413147 | Q423797 | Q6456100 |
Q59627745 [(±) -Norephedrine] | Q59628358 [(±) -Norspeudoephedrine] |
use
Today, norephedrine is mainly used as a medicinal substance in prescription-only anorectics (appetite suppressants) because, like all amphetamines, it has an appetite-suppressing effect. In addition, it is used in combination preparations to alleviate the symptoms of influenza-like infectious diseases because, on the one hand, the vasoconstricting effect promotes the swelling of the nasal mucous membranes and, on the other hand, the cardiovascular system is slightly stimulated.
Its use as a drug is controversial, however, as norephedrine has a particularly pronounced effect on the circulatory system and therefore cardiac arrhythmias and even heart attacks can occur. Similar to ephedrine and other amphetamine derivatives, norephedrine is often misused as a doping or intoxicant. Norephedrine is also used in some cases in the illegal synthesis of amphetamines, since both substances are chemically very similar. In the chemical industry , norephedrine is used in the resolution of carboxylic acids according to the diastereomer method.
Legal
Due to its suitability as a starting material in amphetamine synthesis, norephedrine belongs in Germany and the EU to Category I of the monitored chemicals according to the Basic Substance Monitoring Act . This means that manufacturing, trading and importing or exporting without a permit is a criminal offense.
Trade names
Boxogetten (D), Recatol mono (D)
Anti-obesity (D), Basoplex (D), Wick Daymed cold capsules (D)
Individual evidence
- ↑ a b data sheet (1R, 2S) - (-) - Norephedrine from Sigma-Aldrich , accessed on April 16, 2011 ( PDF ).
- ↑ External identifiers of or database links to (-) - norephedrine hydrochloride : CAS number: 154-41-6, EC number: 205-826-7, ECHA InfoCard: 100.005.298 , PubChem : 62943 , ChemSpider : 56660 , DrugBank : DBSALT000996 , Wikidata : Q27270210 .
- ↑ Entry on Phenylpropanolamine in the DrugBank of the University of Alberta , accessed December 12, 2018.