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Cathine

Chemical compound

Chemical compound

  • Appetite suppressant
  • CNS stimulant

| elimination_half-life = 1.8–8.6 hours

  • (+)-Norpseudoephedrine
  • Cathine
  • (1S,2S)-β-Hydroxyamphetamine

Cathine, also known as D-norpseudoephedrine or as (+)-norpseudoephedrine, is a psychoactive drug of the phenethylamine and amphetamine groups which acts as a stimulant. Along with cathinone, it is found naturally in Catha edulis (khat), and contributes to the overall effects of the plant. Cathine has approximately 7 to 10% of the potency of amphetamine.

Pharmacology

Like amphetamines, cathinone and ephedrine, cathine acts as a norepinephrine releasing agent (NRA).

CompoundRef
Dextroamphetamine (S(+)-amphetamine)6.6–7.2
S(–)-Cathinone12.4
Ephedrine ((–)-ephedrine)43.1–72.4
(+)-Ephedrine218
Dextromethamphetamine (S(+)-methamphetamine)12.3–13.8
Levomethamphetamine (R(–)-methamphetamine)28.5
(+)-Phenylpropanolamine ((+)-norephedrine)42.1
(–)-Phenylpropanolamine ((–)-norephedrine)137
Cathine ((+)-norpseudoephedrine)15.0
(–)-Norpseudoephedrine30.1
(–)-Pseudoephedrine4,092
Pseudoephedrine ((+)-pseudoephedrine)224
Notes: The smaller the value, the more strongly the drug releases the neurotransmitter. The assays were done in rat brain synaptosomes and human potencies may be different. See also Monoamine releasing agent § Activity profiles for a larger table with more compounds. Refs:

Chemistry

Cathine is one of the four stereoisomers of phenylpropanolamine (PPA).

Regulation

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. In the United States, it is classified as a Schedule IV controlled substance.

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

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

Ephedra, found in many Ephedraceae species, is a Chinese and Western herb that contains, among other amphetamines, -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).

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

References

References

  1. Anvisa. (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial". [[Diário Oficial da União]].
  2. (July 2003). "Pharmacokinetics of cathinone, cathine and norephedrine after the chewing of khat leaves". British Journal of Clinical Pharmacology.
  3. (December 2010). "Khat use and neurobehavioral functions: suggestions for future studies". Journal of Ethnopharmacology.
  4. (2020-10-16). "The Appetite Suppressant D-norpseudoephedrine (Cathine) Acts ''via'' D1/D2-Like Dopamine Receptors in the Nucleus Accumbens Shell". Frontiers in Neuroscience.
  5. (January 2001). "Amphetamine-type central nervous system stimulants release norepinephrine more potently than they release dopamine and serotonin". Synapse.
  6. (2013). "Powerful cocaine-like actions of 3,4-methylenedioxypyrovalerone (MDPV), a principal constituent of psychoactive 'bath salts' products". Neuropsychopharmacology.
  7. (October 2003). "In vitro characterization of ephedrine-related stereoisomers at biogenic amine transporters and the receptorome reveals selective actions as norepinephrine transporter substrates". J Pharmacol Exp Ther.
  8. (April 2012). "The designer methcathinone analogs, mephedrone and methylone, are substrates for monoamine transporters in brain tissue". Neuropsychopharmacology.
  9. (2003). "Monoamine transporters and psychostimulant drugs". Eur. J. Pharmacol..
  10. (2006). "Therapeutic potential of monoamine transporter substrates". Curr Top Med Chem.
  11. "Scheduling Actions". U.S. Department Of Justice, Drug Enforcement Administration (DEA).
  12. (March 2019). "Stimulant Use in Pregnancy: An Under-recognized Epidemic Among Pregnant Women". Clinical Obstetrics and Gynecology.
  13. (October 2017). "Correlates of khat use during pregnancy: A cross-sectional study". Addictive Behaviors.
  14. (September 1987). "Use of khat in lactating women: a pilot study on breast-milk secretion". Journal of Ethnopharmacology.
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amphetamine-alkaloids beta-hydroxyamphetamines decongestants euphoriants methamphetamines norepinephrine-dopamine-releasing-agents recreational-drug-metabolites human-drug-metabolites
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