Chemistry:Cathine
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.[1] Cathine has approximately 7 to 10% of the potency of amphetamine.[1]
Pharmacology
Like amphetamines, cathinone and ephedrine, cathine acts as a norepinephrine releasing agent (NRA).[1] It also acts as a dopamine releasing agent (DRA).[1][2]
| Compound | NE | DA | 5-HT | Ref |
|---|---|---|---|---|
| Dextroamphetamine (S(+)-amphetamine) | 6.6–7.2 | 5.8–24.8 | 698–1,765 | [3][4] |
| S(–)-Cathinone | 12.4 | 18.5 | 2,366 | [5] |
| Ephedrine ((–)-ephedrine) | 43.1–72.4 | 236–1,350 | >10,000 | [3] |
| (+)-Ephedrine | 218 | 2,104 | >10,000 | [3][5] |
| Dextromethamphetamine (S(+)-methamphetamine) | 12.3–13.8 | 8.5–24.5 | 736–1,292 | [3][6] |
| Levomethamphetamine (R(–)-methamphetamine) | 28.5 | 416 | 4,640 | [3] |
| (+)-Phenylpropanolamine ((+)-norephedrine) | 42.1 | 302 | >10,000 | [5] |
| (–)-Phenylpropanolamine ((–)-norephedrine) | 137 | 1,371 | >10,000 | [5] |
| Cathine ((+)-norpseudoephedrine) | 15.0 | 68.3 | >10,000 | [5] |
| (–)-Norpseudoephedrine | 30.1 | 294 | >10,000 | [5] |
| (–)-Pseudoephedrine | 4,092 | 9,125 | >10,000 | [5] |
| Pseudoephedrine ((+)-pseudoephedrine) | 224 | 1,988 | >10,000 | [5] |
| 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:[7][8] | ||||
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.[9] In the United States, it is classified as a Schedule IV controlled substance.[10]
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, 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).[11]
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.[12] Among lactating women who chew khat, D-norpseudoephedrine is found in breastmilk.[13]
See also
- L-Norpseudoephedrine, the enantiomer
- Methcathinone
- Ephedra sinica ("Ephedra")
- Ephedrine
- Pseudoephedrine
- Methamphetamine
References
- ↑ 1.0 1.1 1.2 1.3 "Khat use and neurobehavioral functions: suggestions for future studies". Journal of Ethnopharmacology 132 (3): 554–63. December 2010. doi:10.1016/j.jep.2010.05.033. PMID 20553832.
- ↑ "The Appetite Suppressant D-norpseudoephedrine (Cathine) Acts via D1/D2-Like Dopamine Receptors in the Nucleus Accumbens Shell". Frontiers in Neuroscience 14. 2020-10-16. doi:10.3389/fnins.2020.572328. PMID 33177980.
- ↑ 3.0 3.1 3.2 3.3 3.4 "Amphetamine-type central nervous system stimulants release norepinephrine more potently than they release dopamine and serotonin". Synapse 39 (1): 32–41. January 2001. doi:10.1002/1098-2396(20010101)39:1<32::AID-SYN5>3.0.CO;2-3. PMID 11071707.
- ↑ "Powerful cocaine-like actions of 3,4-methylenedioxypyrovalerone (MDPV), a principal constituent of psychoactive 'bath salts' products". Neuropsychopharmacology 38 (4): 552–562. 2013. doi:10.1038/npp.2012.204. PMID 23072836.
- ↑ 5.0 5.1 5.2 5.3 5.4 5.5 5.6 5.7 "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 307 (1): 138–145. October 2003. doi:10.1124/jpet.103.053975. PMID 12954796.
- ↑ "The designer methcathinone analogs, mephedrone and methylone, are substrates for monoamine transporters in brain tissue". Neuropsychopharmacology 37 (5): 1192–203. April 2012. doi:10.1038/npp.2011.304. PMID 22169943.
- ↑ "Monoamine transporters and psychostimulant drugs". Eur. J. Pharmacol. 479 (1–3): 23–40. 2003. doi:10.1016/j.ejphar.2003.08.054. PMID 14612135.
- ↑ "Therapeutic potential of monoamine transporter substrates". Curr Top Med Chem 6 (17): 1845–1859. 2006. doi:10.2174/156802606778249766. PMID 17017961.
- ↑ "List of psychotropic substances under international control". International Narcotics Control Board. http://www.incb.org/pdf/e/list/green.pdf.
- ↑ "Scheduling Actions". Diversion Control Division. U.S. Department Of Justice, Drug Enforcement Administration (DEA). https://www.deadiversion.usdoj.gov/schedules/orangebook/a_sched_alpha.pdf.
- ↑ "Stimulant Use in Pregnancy: An Under-recognized Epidemic Among Pregnant Women". Clinical Obstetrics and Gynecology 62 (1): 168–184. March 2019. doi:10.1097/GRF.0000000000000418. PMID 30601144.
- ↑ "Correlates of khat use during pregnancy: A cross-sectional study". Addictive Behaviors 73: 178–184. October 2017. doi:10.1016/j.addbeh.2017.05.008. PMID 28531823.
- ↑ "Use of khat in lactating women: a pilot study on breast-milk secretion". Journal of Ethnopharmacology 21 (1): 85–90. September 1987. doi:10.1016/0378-8741(87)90097-3. PMID 3695559.
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