Cathine: Difference between revisions

{{Short description|Chemical compound}}

{{Distinguish|Caffeine}}

| class = {{Plainlist|

*[[Appetite suppressant]]

*[[CNS stimulant|{{abbr|CNS|Central nervous system}} stimulant]]

}}

| solubility = 20

| verifiedrevid = 446197235

| drug_name = {{sc|D}}-norpseudoephedrine

| type =

| image = Cathine2DCSD.svg

| width = 150px

| alt =

| caption =

| image2 = Cathine3DanJ.gif

| width2 = 250px

<!--Clinical data-->| tradename =

| MedlinePlus =

| licence_EU =

| licence_US =

| pregnancy_AU =

| pregnancy_US =

| pregnancy_category =

| legal_AU = S4

| legal_BR = A3

| legal_BR_comment = <ref>{{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2023-03-31 |title=RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |url-status=live |archive-url=https://web.archive.org/web/20230803143925/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |archive-date=2023-08-03 |access-date=2023-08-16 |publisher=[[Diário Oficial da União]] |language=pt-BR |publication-date=2023-04-04}}</ref>

| legal_CA = Schedule IV

| legal_DE = Rx-only/Anlage III

| legal_US = Schedule IV

| legal_UK = Class C

| legal_UN = P III

| legal_status =

<!--Pharmacokinetic data-->| bioavailability =

| metabolism =

| elimination_half-life = 1.8–8.6 hours<ref>{{cite journal | vauthors = Toennes SW, Harder S, Schramm M, Niess C, Kauert GF | title = Pharmacokinetics of cathinone, cathine and norephedrine after the chewing of khat leaves | journal = British Journal of Clinical Pharmacology | volume = 56 | issue = 1 | pages = 125–30 | date = July 2003 | pmid = 12848785 | pmc = 1884326 | doi = 10.1046/j.1365-2125.2003.01834.x }}</ref>

<!--Identifiers-->| CAS_number_Ref = {{cascite|correct|??}}

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| synonyms = {{Plainlist|

*(+)-norpseudoephedrine

*Cathine

}}

| ChEMBL = 1412041

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| ChEBI = 4109

| KEGG = D07627

| UNII_Ref = {{fdacite|correct|FDA}}

<!--Chemical data-->| C = 9

| H = 13

| N = 1

| O = 1

'''{{sc|D}}-norpseudoephedrine''', also known as '''cathine''' and '''(+)-norpseudoephedrine''', is a [[psychoactive drug]] of the [[phenethylamine]] and [[amphetamine]] [[chemical class]]es which acts as a [[stimulant]]. Along with [[cathinone]], it is found naturally in ''[[Catha edulis]]'' (khat), and contributes to its overall effects.<ref name="behav2010">{{cite journal | vauthors = Hoffman R, Al'Absi M | title = Khat use and neurobehavioral functions: suggestions for future studies | journal = Journal of Ethnopharmacology | volume = 132 | issue = 3 | pages = 554–63 | date = December 2010 | pmid = 20553832 | pmc = 2976806 | doi = 10.1016/j.jep.2010.05.033 }}</ref> It has approximately 7-10% the potency of [[amphetamine]].<ref name = behav2010/>

Like [[amphetamine]]s, cathinone and [[ephedrine]], cathine acts as a [[norepinephrine releasing agent]] (NRA).<ref name = behav2010/> It also acts as a [[dopamine releasing agent]] (DRA).<ref name = behav2010/><ref>{{cite journal | vauthors = Kalyanasundar B, Perez CI, Arroyo B, Moreno MG, Gutierrez R | title = The Appetite Suppressant D-norpseudoephedrine (Cathine) Acts ''via'' D1/D2-Like Dopamine Receptors in the Nucleus Accumbens Shell | journal = Frontiers in Neuroscience | volume = 14 | pages = 572328 | date = 2020-10-16 | pmid = 33177980 | pmc = 7596745 | doi = 10.3389/fnins.2020.572328 | doi-access = free }}</ref>

Cathine is one of the four [[Stereoisomerism|stereoisomers]] of [[phenylpropanolamine]] (PPA).

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 [[microgram]]s per [[milliliter]] in [[urine]]. Cathine is a [[Convention on Psychotropic Substances#Schedules of Controlled Substances|Schedule III]] drug under the [[Convention on Psychotropic Substances]].<ref name="List of controlled substances" /> In the United States, it is classified as a Schedule IV [[controlled substance]].<ref>{{cite web | title = Scheduling Actions | url = https://www.deadiversion.usdoj.gov/schedules/orangebook/a_sched_alpha.pdf | work = Diversion Control Division | publisher = U.S. Department Of Justice, Drug Enforcement Administration (DEA) }}</ref>

In Australia, Cathine is officially a [[Standard for the Uniform Scheduling of Medicines and Poisons|schedule 4]] drug prescription only, but is not available or approved for any medical use.

[[File:Catha edulis.jpg|thumb|250px|left|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 (medicine)|Ephedra]], found in many ''[[Ephedraceae]]'' species, is a Chinese and Western herb that contains, among other amphetamines, {{sc|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]] [[Statistical association|association]] to women not using ephedra ([[odds ratio]] 2.8, [[confidence interval]] 1.0–7.3).<ref>{{cite journal | vauthors = Smid MC, Metz TD, Gordon AJ | title = Stimulant Use in Pregnancy: An Under-recognized Epidemic Among Pregnant Women | journal = Clinical Obstetrics and Gynecology | volume = 62 | issue = 1 | pages = 168–184 | date = March 2019 | pmid = 30601144 | pmc = 6438363 | doi = 10.1097/GRF.0000000000000418 }}</ref>

A small study of 642 participants in Yemen found that among pregnant women who chewed khat (containing {{sc|D}}-norpseudoephedrine) there was no increased risk of [[stillbirth]] or [[Birth defect|congenital malformations]].<ref>{{cite journal | vauthors = Nakajima M, Jebena MG, Taha M, Tesfaye M, Gudina E, Lemieux A, Hoffman R, al'Absi M | display-authors = 6 | title = Correlates of khat use during pregnancy: A cross-sectional study | journal = Addictive Behaviors | volume = 73 | pages = 178–184 | date = October 2017 | pmid = 28531823 | doi = 10.1016/j.addbeh.2017.05.008 }}</ref> Among lactating women who chew khat, {{sc|D}}-norpseudoephedrine is found in [[breastmilk]].<ref>{{cite journal | vauthors = Kristiansson B, Abdul Ghani N, Eriksson M, Garle M, Qirbi A | title = Use of khat in lactating women: a pilot study on breast-milk secretion | journal = Journal of Ethnopharmacology | volume = 21 | issue = 1 | pages = 85–90 | date = September 1987 | pmid = 3695559 | doi = 10.1016/0378-8741(87)90097-3 }}</ref>

* [[L-Norpseudoephedrine|{{sc|L}}-Norpseudoephedrine]], the [[enantiomer]]

* ''[[Ephedra sinica]]'' ("Ephedra")

{{Reflist|refs=

<ref name="List of controlled substances">

{{cite web

| url = http://www.incb.org/pdf/e/list/green.pdf

| archive-url = https://web.archive.org/web/20120831222336/http://www.incb.org/pdf/e/list/green.pdf

| archive-date = 2012-08-31

| title = List of psychotropic substances under international control

| work = International Narcotics Control Board

}}</ref>}}

{{Monoamine releasing agents}}

[[Category:Phenylethanolamines]]

[[Category:Norepinephrine-dopamine releasing agents]]