Cathine

Not to be confused with Caffeine.

D-NORPSEUDOEPHEDRINE

Clinical data

Other names (+)-norpseudoephedrine

Cathine

Routes of Oral
administration

Drug class Appetite suppressant

CNS stimulant

ATC code A08AA07 (WHO)

Legal status

Legal status AU: S4 (Prescription only)

BR: Class A3 (Psychoactive drugs)[1]

CA: Schedule IV

DE: Prescription only (Anlage III for higher

doses)
UK: Class C

US: Schedule IV

UN: Psychotropic Schedule III

 Pharmacokinetic data

Elimination half-life 1.8–8.6 hours[2]

Identifiers

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IUPAC name

CAS Number 492-39-7

PubChem CID 441457

DrugBank DB01486

ChemSpider 390189

UNII E1L4ZW2F8O

KEGG D07627

ChEBI CHEBI:4109

ChEMBL ChEMBL1412041

CompTox DTXSID50889347
Dashboard (EPA)

ECHA InfoCard 100.007.050

Chemical and physical data

Formula C9H13NO

Molar mass 151.209 g·mol−1

3D model (JSmol) Interactive image

Solubility in water 20 mg/mL (20 °C)

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SMILES

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InChI

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D-norpseudoephedrine, also known as cathine and (+)-norpseudoephedrine, is

a psychoactive drug of the phenethylamine and amphetamine chemical classes which
acts as a stimulant. Along with cathinone, it is found naturally in Catha edulis (khat), and
contributes to its overall effects.[3] It has approximately 7-10% the potency
of amphetamine.[3]
Pharmacology[edit]
Like amphetamines, cathinone and ephedrine, cathine acts as a norepinephrine
releasing agent (NRA).[3] It also acts as a dopamine releasing agent (DRA).[3][4]

Chemistry[edit]
Cathine is one of the four stereoisomers of phenylpropanolamine (PPA).

Regulation[edit]
The World Anti-Doping Agency's list of prohibited substances (used for the Olympic
Games among other athletic events) bans cathine in concentrations of over
5 micrograms per milliliter in urine. Cathine is a Schedule III drug under the Convention
on Psychotropic Substances.[5] In the United States, it is classified as a Schedule
IV controlled substance.[6]

In Australia, Cathine is officially a schedule 4 drug prescription only, but is not available
or approved for any medical use.

Cathine is found in the shrub khat (Catha edulis).

In Hong Kong, cathine is regulated under Schedule 1 of Hong Kong's Chapter
134 Dangerous Drugs Ordinance. Unlawful possession is punishable by severe fines
and imprisonment.

Pregnancy[edit]
Ephedra, found in many Ephedraceae species, is a Chinese and Western herb that
contains, among other amphetamines, D-norpseudoephedrine. In the National Birth
Defects Prevention Study, which included 18,438 women from 10 states from 1999 to
2003, 1.3% of women reported using ephedra during pregnancy. During the trial, five
cases of anencephaly were born to women who used ephedra, however there was
no statistically significant association to women not using ephedra (odds
ratio 2.8, confidence interval 1.0–7.3).[7]

A small study of 642 participants in Yemen found that among pregnant women who
chewed khat (containing D-norpseudoephedrine) there was no increased risk
of stillbirth or congenital malformations.[8] Among lactating women who chew khat, D-
norpseudoephedrine is found in breastmilk.[9]

See also[edit]
 L-Norpseudoephedrine, the enantiomer
 Methcathinone
 Ephedra sinica ("Ephedra")
 Ephedrine
 Pseudoephedrine
 Methamphetamine