Cathine

D-norpseudoephedrine
Clinical data
Other names	(+)-Norpseudoephedrine; Cathine; (1S,2S)-β-Hydroxyamphetamine;
Routes of; administration	Oral
Drug class	Appetite suppressant; CNS stimulant;
ATC code	A08AA07 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); BR: Class A3 (Psychoactive drugs); 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
Identifiers
	IUPAC name (1S,2S)-2-amino-1-phenylpropan-1-ol;
CAS Number	492-39-7 ;
PubChem CID	441457;
DrugBank	DB01486 ;
ChemSpider	390189 ;
UNII	E1L4ZW2F8O;
KEGG	D07627;
ChEBI	CHEBI:4109;
ChEMBL	ChEMBL1412041 ;
CompTox Dashboard (EPA)	DTXSID50889347 ;
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)
	SMILES O[C@@H](c1ccccc1)[C@@H](N)C;
	InChI 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 ; Key:DLNKOYKMWOXYQA-IONNQARKSA-N ;
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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

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

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.^[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

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]

References

^ 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 Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
^ 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.
^ ^a ^b ^c ^d 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.
^ 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.
^ "List of psychotropic substances under international control" (PDF). International Narcotics Control Board. Archived from the original (PDF) on 2012-08-31.
^ "Scheduling Actions" (PDF). Diversion Control Division. U.S. Department Of Justice, Drug Enforcement Administration (DEA).
^ 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.
^ 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.
^ 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.

[1] 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 Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.

[2] 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.

[behav2010-3] 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] 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.

[List_of_controlled_substances-5] "List of psychotropic substances under international control" (PDF). International Narcotics Control Board. Archived from the original (PDF) on 2012-08-31.

[6] "Scheduling Actions" (PDF). Diversion Control Division. U.S. Department Of Justice, Drug Enforcement Administration (DEA).

[7] 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.

[8] 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.

[9] 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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