Norephedrine

Structural formula
Structural formula of L- norephedrine
General
Non-proprietary name	Phenylpropanolamine
other names	Norephedrine 2-amino-1-phenyl-propan-1-ol PPA Naldecon
Molecular formula	C 9 H 13 NO
External identifiers / databases
CAS number 14838-15-4 [(±) -Norephedrine] EC number 238-900-2 ECHA InfoCard 100.035.349 PubChem 4786 ChemSpider 142493 DrugBank DB00397 Wikidata Q59627745
Drug information
ATC code	R01 BA01
Drug class	Sympathomimetic
properties
Molar mass	151.21 g mol −1
safety instructions
Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed GHS labeling of hazardous substances Caution H and P phrases H: 302-315-319-335 P: 261-305 + 351 + 338
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 Cathine	(-) - 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

Monopreparations

Boxogetten (D), Recatol mono (D)

Combination preparations

Anti-obesity (D), Basoplex (D), Wick Daymed cold capsules (D)

Individual evidence

1. ↑ ^{a b} data sheet (1R, 2S) - (-) - Norephedrine from Sigma-Aldrich , accessed on April 16, 2011 ( PDF ).
2. ↑ 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 .
3. ↑ Entry on Phenylpropanolamine in the DrugBank of the University of Alberta , accessed December 12, 2018.

This article is about a health issue. It is not used for self-diagnosis and does not replace a diagnosis by a doctor. Please note the information on health issues !