Editing Ephedrine (section)

==Pharmacology==
===Pharmacodynamics===
{| class="wikitable sortable floatright" style="font-size:small;"
|+ Monoamine release by ephedrine and related agents ({{Abbrlink|EC<sub>50</sub>|half maximal effective concentration}}, nM)<ref name="RothmanBaumann2003">{{cite journal | vauthors = Rothman RB, Baumann MH | title = Monoamine transporters and psychostimulant drugs | journal = Eur. J. Pharmacol. | volume = 479 | issue = 1–3 | pages = 23–40 | year = 2003 | pmid = 14612135 | doi = 10.1016/j.ejphar.2003.08.054}}</ref><ref name="RothmanBaumann2006">{{cite journal | vauthors = Rothman RB, Baumann MH | title = Therapeutic potential of monoamine transporter substrates | journal = Curr Top Med Chem | volume = 6 | issue = 17 | pages = 1845–1859 | date = 2006 | pmid = 17017961 | doi = 10.2174/156802606778249766 | url = }}</ref>
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! Compound !! data-sort-type="number" | {{abbrlink|NE|Norepinephrine}} !! data-sort-type="number" | {{abbrlink|DA|Dopamine}} !! data-sort-type="number" | {{abbrlink|5-HT|Serotonin}} !! Ref
|-
| [[Dextroamphetamine]] (''S''(+)-amphetamine) || 6.6–7.2 || 5.8–24.8 || 698–1765 || <ref name="RothmanBaumannDersch2001">{{cite journal | vauthors = Rothman RB, Baumann MH, Dersch CM, Romero DV, Rice KC, Carroll FI, Partilla JS | title = Amphetamine-type central nervous system stimulants release norepinephrine more potently than they release dopamine and serotonin | journal = Synapse | volume = 39 | issue = 1 | pages = 32–41 | date = January 2001 | pmid = 11071707 | doi = 10.1002/1098-2396(20010101)39:1<32::AID-SYN5>3.0.CO;2-3 | url = }}</ref><ref name="BaumannPartillaLehner2013">{{cite journal | vauthors = 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 | title = Powerful cocaine-like actions of 3,4-methylenedioxypyrovalerone (MDPV), a principal constituent of psychoactive 'bath salts' products | journal = Neuropsychopharmacology | volume = 38 | issue = 4 | pages = 552–562 | year = 2013 | pmid = 23072836 | pmc = 3572453 | doi = 10.1038/npp.2012.204 }}</ref>
|-
| [[Cathinone|''S''(–)-Cathinone]] || 12.4 || 18.5 || 2366 || <ref name="RothmanVuPartilla2003">{{cite journal | vauthors = Rothman RB, Vu N, Partilla JS, Roth BL, Hufeisen SJ, Compton-Toth BA, Birkes J, Young R, Glennon RA | title = In vitro characterization of ephedrine-related stereoisomers at biogenic amine transporters and the receptorome reveals selective actions as norepinephrine transporter substrates | journal = J Pharmacol Exp Ther | volume = 307 | issue = 1 | pages = 138–145 | date = October 2003 | pmid = 12954796 | doi = 10.1124/jpet.103.053975 | url = }}</ref>
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| Ephedrine ((–)-ephedrine) || 43.1–72.4 || 236–1350 || >10000 || <ref name="RothmanBaumannDersch2001" />
|-
| (+)-Ephedrine || 218 || 2104 || >10000 || <ref name="RothmanBaumannDersch2001" /><ref name="RothmanVuPartilla2003" />
|-
| [[Dextromethamphetamine]] (''S''(+)-methamphetamine) || 12.3–13.8 || 8.5–24.5 || 736–1291.7 || <ref name="RothmanBaumannDersch2001" /><ref name="BaumannAyestasPartilla2012">{{cite journal | vauthors = Baumann MH, Ayestas MA, Partilla JS, Sink JR, Shulgin AT, Daley PF, Brandt SD, Rothman RB, Ruoho AE, Cozzi NV | title = The designer methcathinone analogs, mephedrone and methylone, are substrates for monoamine transporters in brain tissue | journal = Neuropsychopharmacology | volume = 37 | issue = 5 | pages = 1192–203 | date = April 2012 | pmid = 22169943 | pmc = 3306880 | doi = 10.1038/npp.2011.304 | url = }}</ref>
|-
| [[Levomethamphetamine]] (''R''(–)-methamphetamine) || 28.5 || 416 || 4640 || <ref name="RothmanBaumannDersch2001" />
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| [[Phenylpropanolamine|(+)-Phenylpropanolamine]] ((+)-norephedrine) || 42.1 || 302 || >10000 || <ref name="RothmanVuPartilla2003" />
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| [[Phenylpropanolamine|(–)-Phenylpropanolamine]] ((–)-norephedrine) || 137 || 1371 || >10000 || <ref name="RothmanVuPartilla2003" />
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| [[Cathine]] ((+)-norpseudoephedrine) || 15.0 || 68.3 || >10000 || <ref name="RothmanVuPartilla2003" />
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| [[L-Norpseudoephedrine|(–)-Norpseudoephedrine]] || 30.1 || 294 || >10000 || <ref name="RothmanVuPartilla2003" />
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| (–)-Pseudoephedrine || 4092 || 9125 || >10000 || <ref name="RothmanVuPartilla2003" />
|-
| [[Pseudoephedrine]] ((+)-pseudoephedrine) || 224 || 1988 || >10000 || <ref name="RothmanVuPartilla2003" />
|-
| colspan="7" style="width: 1px; background-color:#eaecf0; text-align: center;" | '''Notes:''' The smaller the value, the more strongly the substance releases the neurotransmitter. See also [[Monoamine releasing agent#Activity profiles|Monoamine releasing agent § Activity profiles]] for a larger table with more compounds.
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|}

Ephedrine, a [[sympathomimetic amine]], acts on part of the [[sympathetic nervous system]] (SNS). The principal mechanism of action relies on its indirect stimulation of the [[adrenergic receptor]] system by increasing activation of [[α-adrenergic receptor|α-]] and [[β-adrenergic receptor]]s via [[norepinephrine releasing agent|induction of norepinephrine release]].<ref name=merck>{{cite web | url = http://www.merckmanuals.com/professional/lexicomp/ephedrine.html | date = January 2010 | work = Merck Manuals | title = EPHEDrine | archive-url = https://web.archive.org/web/20110324031411/http://www.merckmanuals.com/professional/lexicomp/ephedrine.html | archive-date = 24 March 2011 }}</ref> The presence of direct interactions with α-adrenergic receptors is unlikely but still controversial.<ref name="Docherty2008" /><ref name='drew'/><ref name="Ma_2007">{{cite journal | vauthors = Ma G, Bavadekar SA, Davis YM, Lalchandani SG, Nagmani R, Schaneberg BT, Khan IA, Feller DR | display-authors = 6 | title = Pharmacological effects of ephedrine alkaloids on human alpha(1)- and alpha(2)-adrenergic receptor subtypes | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 322 | issue = 1 | pages = 214–221 | date = July 2007 | pmid = 17405867 | doi = 10.1124/jpet.107.120709 | s2cid = 86429875 }}</ref><ref name="pmid14570629">{{cite journal | vauthors = Kobayashi S, Endou M, Sakuraya F, Matsuda N, Zhang XH, Azuma M, Echigo N, Kemmotsu O, Hattori Y, Gando S | display-authors = 6 | title = The sympathomimetic actions of l-ephedrine and d-pseudoephedrine: direct receptor activation or norepinephrine release? | journal = Anesthesia and Analgesia | volume = 97 | issue = 5 | pages = 1239–1245 | date = November 2003 | pmid = 14570629 | doi = 10.1213/01.ANE.0000092917.96558.3C | doi-access = free }}</ref> <small>L</small>-ephedrine, and particularly its stereoisomer [[norpseudoephedrine]] (which is also present in ''[[Catha edulis]]'') has indirect [[sympathomimetic]] effects and due to its ability to cross the [[blood–brain barrier]], it is a [[Central nervous system|CNS]] [[stimulant]] similar to [[amphetamine]]s, but less pronounced, as it releases norepinephrine and [[dopamine]] in the [[brain]].<ref>{{cite journal | vauthors = Munhall AC, Johnson SW | title = Dopamine-mediated actions of ephedrine in the rat substantia nigra | journal = Brain Research | volume = 1069 | issue = 1 | pages = 96–103 | date = January 2006 | pmid = 16386715 | doi = 10.1016/j.brainres.2005.11.044 | s2cid = 40626692 }}</ref>

===Pharmacokinetics===
====Absorption====
The [[oral administration|oral]] [[bioavailability]] of ephedrine is 88%.<ref name="DrugBank" /> The [[onset of action]] of ephedrine orally is 15 to 60{{nbsp}}minutes, via [[intramuscular injection]] is 10 to 20{{nbsp}}minutes, and via [[intravenous infusion]] is within seconds.<ref name="AHFS2016" />

====Distribution====
Its [[plasma protein binding]] is approximately 24 to 29%, with 5 to 10% bound to [[human serum albumin|albumin]].<ref name="VolppHolzgrabe2019" /><ref name="Schmidt2023" /><ref name="GadAzabKhattab2021" />

====Metabolism====
Ephedrine is largely not [[drug metabolism|metabolized]].<ref name="DrugBank" /> [[Norephedrine]] (phenylpropanolamine) is an [[active metabolite]] of ephedrine formed via ''N''-[[demethylation]].<ref name="DrugBank" /><ref name="ChuaBenrimojTriggs1989" /> About 8 to 20% of an oral dose of ephedrine is demethylated into norephedrine, about 4 to 13% is [[oxidation|oxidatively]] [[deamination|deaminated]] into [[benzoic acid]], and a small fraction is converted into 1,2-dihydroxy-1-phenylpropane.<ref name="ChuaBenrimojTriggs1989" />

====Elimination====
Ephedrine is [[elimination (pharmacology)|eliminated]] mainly in [[urine]], with 60% (range 53–79%) [[excretion|excreted]] unchanged.<ref name="DrugBank" /><ref name="ChuaBenrimojTriggs1989" />

The [[elimination half-life]] of ephedrine is 6{{nbsp}}hours.<ref name="DrugBank" /> Its [[duration of action]] orally is 2 to 4{{nbsp}}hours and via intravenous or intramuscular injection is 60{{nbsp}}minutes.{{Citation needed|date=August 2024}}

The elimination of ephedrine is dependent on urinary [[pH]].<ref name="ChuaBenrimojTriggs1989" />