Cathine

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Cathine
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Clinical data
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  • (+)-Norpseudoephedrine
  • Cathine
  • (1S,2S)-β-Hydroxyamphetamine
Routes of
administration		Oral
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Legal status
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Pharmacokinetic data
Elimination half-life1.8–8.6 hours[2]
Identifiers
  • (1S,2S)-2-amino-1-phenylpropan-1-ol
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E number{{#property:P628}}
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Chemical and physical data
FormulaC9H13NO
Molar mass151.209 g·mol−1
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Solubility in water20 mg/mL (20 °C)
  • O[C@@H](c1ccccc1)[C@@H](N)C
  • InChI=1S/C9H13NO/c1-7(10)9(11)8-5-3-2-4-6-8/h2-7,9,11H,10H2,1H3/t7-,9+/m0/s1 checkY
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Data page
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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.[3] Cathine has approximately 7 to 10% of the potency of amphetamine.[3]

Pharmacology

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]

Monoamine release by cathine and related agents (EC50Tooltip half maximal effective concentration, nM)
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. 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:[9][10]

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.[11] In the United States, it is classified as a Schedule IV controlled substance.[12]

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

Ephedra, found in many Ephedraceae species, is a Chinese and Western herb that contains, among other amphetamines, Page Template:Smallcaps/styles.css has no content.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).[13]

A small study of 642 participants in Yemen found that among pregnant women who chewed khat (containing Page Template:Smallcaps/styles.css has no content.D-norpseudoephedrine) there was no increased risk of stillbirth or congenital malformations.[14] Among lactating women who chew khat, Page Template:Smallcaps/styles.css has no content.D-norpseudoephedrine is found in breastmilk.[15]

See also

References

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  1. ^ Page Module:Citation/CS1/styles.css has no content.Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in português do Brasil). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
  2. ^ Page Module:Citation/CS1/styles.css has no content.Toennes SW, Harder S, Schramm M, Niess C, Kauert GF (July 2003). "Pharmacokinetics of cathinone, cathine and norephedrine after the chewing of khat leaves". British Journal of Clinical Pharmacology. 56 (1): 125–30. doi:10.1046/j.1365-2125.2003.01834.x. PMC 1884326. PMID 12848785.
  3. ^ a b c d Page Module:Citation/CS1/styles.css has no content.Hoffman R, Al'Absi M (December 2010). "Khat use and neurobehavioral functions: suggestions for future studies". Journal of Ethnopharmacology. 132 (3): 554–63. doi:10.1016/j.jep.2010.05.033. PMC 2976806. PMID 20553832.
  4. ^ Page Module:Citation/CS1/styles.css has no content.Kalyanasundar B, Perez CI, Arroyo B, Moreno MG, Gutierrez R (2020-10-16). "The Appetite Suppressant D-norpseudoephedrine (Cathine) Acts via D1/D2-Like Dopamine Receptors in the Nucleus Accumbens Shell". Frontiers in Neuroscience. 14 572328. doi:10.3389/fnins.2020.572328. PMC 7596745. PMID 33177980.
  5. ^ a b c d e Page Module:Citation/CS1/styles.css has no content.Rothman RB, Baumann MH, Dersch CM, Romero DV, Rice KC, Carroll FI, Partilla JS (January 2001). "Amphetamine-type central nervous system stimulants release norepinephrine more potently than they release dopamine and serotonin". Synapse. 39 (1): 32–41. doi:10.1002/1098-2396(20010101)39:1<32::AID-SYN5>3.0.CO;2-3. PMID 11071707.
  6. ^ Page Module:Citation/CS1/styles.css has no content.Baumann MH, Partilla JS, Lehner KR, Thorndike EB, Hoffman AF, Holy M, Rothman RB, Goldberg SR, Lupica CR, Sitte HH, Brandt SD, Tella SR, Cozzi NV, Schindler CW (2013). "Powerful cocaine-like actions of 3,4-methylenedioxypyrovalerone (MDPV), a principal constituent of psychoactive 'bath salts' products". Neuropsychopharmacology. 38 (4): 552–562. doi:10.1038/npp.2012.204. PMC 3572453. PMID 23072836.
  7. ^ a b c d e f g h Page Module:Citation/CS1/styles.css has no content.Rothman RB, Vu N, Partilla JS, Roth BL, Hufeisen SJ, Compton-Toth BA, Birkes J, Young R, Glennon RA (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. 307 (1): 138–145. doi:10.1124/jpet.103.053975. PMID 12954796.
  8. ^ Page Module:Citation/CS1/styles.css has no content.Baumann MH, Ayestas MA, Partilla JS, Sink JR, Shulgin AT, Daley PF, Brandt SD, Rothman RB, Ruoho AE, Cozzi NV (April 2012). "The designer methcathinone analogs, mephedrone and methylone, are substrates for monoamine transporters in brain tissue". Neuropsychopharmacology. 37 (5): 1192–203. doi:10.1038/npp.2011.304. PMC 3306880. PMID 22169943.
  9. ^ Page Module:Citation/CS1/styles.css has no content.Rothman RB, Baumann MH (2003). "Monoamine transporters and psychostimulant drugs". Eur. J. Pharmacol. 479 (1–3): 23–40. doi:10.1016/j.ejphar.2003.08.054. PMID 14612135.
  10. ^ Page Module:Citation/CS1/styles.css has no content.Rothman RB, Baumann MH (2006). "Therapeutic potential of monoamine transporter substrates". Curr Top Med Chem. 6 (17): 1845–1859. doi:10.2174/156802606778249766. PMID 17017961.
  11. ^ Page Module:Citation/CS1/styles.css has no content."List of psychotropic substances under international control" (PDF). International Narcotics Control Board. Archived from the original (PDF) on 2012-08-31.
  12. ^ Page Module:Citation/CS1/styles.css has no content."Scheduling Actions" (PDF). Diversion Control Division. U.S. Department Of Justice, Drug Enforcement Administration (DEA).
  13. ^ Page Module:Citation/CS1/styles.css has no content.Smid MC, Metz TD, Gordon AJ (March 2019). "Stimulant Use in Pregnancy: An Under-recognized Epidemic Among Pregnant Women". Clinical Obstetrics and Gynecology. 62 (1): 168–184. doi:10.1097/GRF.0000000000000418. PMC 6438363. PMID 30601144.
  14. ^ Page Module:Citation/CS1/styles.css has no content.Nakajima M, Jebena MG, Taha M, Tesfaye M, Gudina E, Lemieux A, et al. (October 2017). "Correlates of khat use during pregnancy: A cross-sectional study". Addictive Behaviors. 73: 178–184. doi:10.1016/j.addbeh.2017.05.008. PMID 28531823.
  15. ^ Page Module:Citation/CS1/styles.css has no content.Kristiansson B, Abdul Ghani N, Eriksson M, Garle M, Qirbi A (September 1987). "Use of khat in lactating women: a pilot study on breast-milk secretion". Journal of Ethnopharmacology. 21 (1): 85–90. doi:10.1016/0378-8741(87)90097-3. PMID 3695559.

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