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| Routes of administration | Oral |
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| Eliminationhalf-life | 1.8–8.6 hours[2] |
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| CompTox Dashboard(EPA) | |
| ECHA InfoCard | 100.007.050 |
| Chemical and physical data | |
| Formula | C9H13NO |
| Molar mass | 151.209 g·mol−1 |
| 3D model (JSmol) | |
| Solubility in water | 20 mg/mL (20 °C) |
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Cathine, also known asD-norpseudoephedrine or as(+)-norpseudoephedrine, is apsychoactive drug of thephenethylamine andamphetamine groups which acts as astimulant. Along withcathinone, it is found naturally inCatha edulis (khat), and contributes to the overall effects of the plant.[3] Cathine has approximately 7 to 10% of thepotency ofamphetamine.[3]
Likeamphetamines, cathinone andephedrine, cathine acts as anorepinephrine releasing agent (NRA).[3] It also acts as adopamine releasing agent (DRA).[3][4]
| Compound | NETooltip Norepinephrine | DATooltip Dopamine | 5-HTTooltip Serotonin | Ref |
|---|---|---|---|---|
| Dextroamphetamine (S(+)-amphetamine) | 6.6–7.2 | 5.8–24.8 | 698–1,765 | [5][6] |
| S(–)-Cathinone | 12.4 | 18.5 | 2,366 | [7] |
| Ephedrine ((–)-ephedrine) | 43.1–72.4 | 236–1,350 | >10,000 | [5] |
| (+)-Ephedrine | 218 | 2,104 | >10,000 | [5][7] |
| Dextromethamphetamine (S(+)-methamphetamine) | 12.3–13.8 | 8.5–24.5 | 736–1,292 | [5][8] |
| Levomethamphetamine (R(–)-methamphetamine) | 28.5 | 416 | 4,640 | [5] |
| (+)-Phenylpropanolamine ((+)-norephedrine) | 42.1 | 302 | >10,000 | [7] |
| (–)-Phenylpropanolamine ((–)-norephedrine) | 137 | 1,371 | >10,000 | [7] |
| Cathine ((+)-norpseudoephedrine) | 15.0 | 68.3 | >10,000 | [7] |
| (–)-Norpseudoephedrine | 30.1 | 294 | >10,000 | [7] |
| (–)-Pseudoephedrine | 4,092 | 9,125 | >10,000 | [7] |
| Pseudoephedrine ((+)-pseudoephedrine) | 224 | 1,988 | >10,000 | [7] |
| Notes: The smaller the value, the more strongly the drug releases the neurotransmitter. Theassays were done in rat brainsynaptosomes and humanpotencies may be different. See alsoMonoamine releasing agent § Activity profiles for a larger table with more compounds.Refs:[9][10] | ||||
Cathine is one of the fourstereoisomers ofphenylpropanolamine (PPA).
TheWorld Anti-Doping Agency's list of prohibited substances (used for theOlympic Games among other athletic events) bans cathine in concentrations of over 5micrograms permilliliter inurine. Cathine is aSchedule III drug under theConvention on Psychotropic Substances.[11] In the United States, it is classified as a Schedule IVcontrolled substance.[12]
In Australia, Cathine is officially aschedule 4 drug prescription only, but is not available or approved for any medical use.
InHong Kong, cathine is regulated under Schedule 1 of Hong Kong's Chapter 134Dangerous Drugs Ordinance. Unlawful possession is punishable by severe fines and imprisonment.
Ephedra, found in manyEphedraceae 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 ofanencephaly were born to women who used ephedra, however there was nostatistically significantassociation to women not using ephedra (odds ratio 2.8,confidence interval 1.0–7.3).[13]
A small study of 642 participants in Yemen found that among pregnant women who chewed khat (containingD-norpseudoephedrine) there was no increased risk ofstillbirth orcongenital malformations.[14] Among lactating women who chew khat,D-norpseudoephedrine is found inbreastmilk.[15]