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Norpseudoephedrine

CAS number 14838-15-4

Identification

Synonyms Phenylpropanolamine
Molecular Structure Norpseudoephedrine,
Phenylpropanolamine,
Molecular Formula C9H13NO
Molecular Weight 151.21
CAS Registry Number 14838-15-4
EINECS 238-900-2

Closely related to ephedrine, cathinone and other amphetamines, it may contribute to the stimulant effect of Catha edulis, although another constituent, cathinone appears to show stronger activity.

Norpseudoephedrine (1RS,2RS)-2-Amino-1-phenylpropan-1-ole, C9H13NO, MW 151,21 g/mol. The (1S,2S)-Isomer is called Cathine.

Norpseudoephedrine is a scheduled (S2) substance, used as anorexigenic (class A.11.3).

As stimulant, Norpseudoephedrine is included in the doping list of the IOC if a limit value of more than 5 µg/ml in the urine is exceeded.

Norpseudoephedrine is one of the optical isomers of phenylpropanolamine, an appetite suppressant and decongestant which is possibly associated with an increased risk of hemorrhagic stroke.

The World Anti-Doping Agency's list of prohibited substances (used for the Olympic Games among other athletic events) bars cathine in concentrations of over 5 micrograms per milliliter in urine.

Norpseudoephedrine is a Schedule III drug under the Convention on Psychotropic Substances.

In order to investigate effects of khat chewing on uteroplacental blood flow (+) norpseudoephedrine (NPE) infusions were given to 11 anesthetized guinea pigs in late pregnancy (62-66 days) after unilateral uterine artery ligation at days 30-32.

Regional blood flows were determined with radioactive microspheres.

Mean arterial blood pressure increased with 25% and heart rate with 9% during NPE infusion. Myoendometrial blood flow was reduced by 31 %. Placental vascular resistance (PVR) increased by 56% in the control horn (17 fetuses) and by 82% in the ligated horn (17 fetuses).

This vasoconstriction was counteracted by the systemic vasopressor response since placental blood flow remained unchanged. When considering only the 13 growth-retarded fetuses, however, PVR increased by 98% and a 19% reduction of placental blood flow could be demonstrated.

These results suggest that the placenta of the growth-retarded fetus may be more sensitive to adrenergic stimulation than the normal placenta.

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