Editing Modafinil (section)

==Chemistry==
===Enantiomers===
<div class="skin-invert-image">{{Multiple image
| direction  = horizontal
| align      = right
| image1     = (R)-(−)-modafinil.svg
| width1     = 180
| caption1   = [[Armodafinil]] ((''R'')-(−)-modafinil)
| image2     = (S)-(+)-modafinil.svg
| width2     = 180
| caption2   = [[Esmodafinil]] ((''S'')-(+)-modafinil)
}}</div>

Modafinil is a [[racemic mixture]] of two [[enantiomer]]s, [[armodafinil]] ((''R'')-modafinil) and [[esmodafinil]] ((''S'')-modafinil).<ref name="pmid20307223">{{cite journal | vauthors = Bogan RK | title = Armodafinil in the treatment of excessive sleepiness | journal = Expert Opinion on Pharmacotherapy | volume = 11 | issue = 6 | pages = 993–1002 | date = April 2010 | pmid = 20307223 | pmc = 3630938 | doi = 10.1517/14656561003705738 }}</ref>

===Detection in body fluids===
Modafinil and/or its major metabolite, modafinil acid, may be quantified in plasma, serum, or urine to monitor dosage in those receiving the drug therapeutically, to confirm a diagnosis of poisoning in hospitalized patients, or to assist in the forensic investigation of a vehicular traffic violation.<ref name="judexbelarus-2018">{{cite journal|url=https://elibrary.ru/item.asp?id=36403188|title=Analytical characteristics and identification of modafinil and adrafinil in the objects of examination|vauthors=Polyakov YS, Mikhniuk ON, Hilkevich TY, Chevtchouk TA, Yurchenko RA, Vinarskiy VA|publisher=State Institute for Advanced Training and Retraining of Customs Authorities of the Republic of Belarus|issn=2413-6158|journal=Судебная экспертиза Беларуси|year=2018|access-date=February 6, 2024|archive-date=September 28, 2020|archive-url=https://web.archive.org/web/20200928001949/https://www.elibrary.ru/item.asp?id=36403188|url-status=live}}</ref> Instrumental techniques involving gas or liquid chromatography are usually employed for these purposes.<ref name="pmid16142993"/><ref name="pmid9549666">{{cite journal | vauthors = Wong YN, King SP, Laughton WB, McCormick GC, Grebow PE | title = Single-dose pharmacokinetics of modafinil and methylphenidate given alone or in combination in healthy male volunteers | journal = Journal of Clinical Pharmacology | volume = 38 | issue = 3 | pages = 276–282 | date = March 1998 | pmid = 9549666 | doi = 10.1002/j.1552-4604.1998.tb04425.x | s2cid = 26877375 }}</ref><ref name="Baselt-2008">{{cite book | vauthors = Baselt RC |title=Disposition of Toxic Drugs and Chemicals in Man |publisher=Biomedical Publications |location=Foster City, CA |year=2008 |isbn=978-0-9626523-7-0 |pages=1152–1153}}</ref> In 2011, modafinil was not tested for by common [[Drug test|drug screens]] (except for anti-doping screens) and is unlikely to cause false positives for other chemically unrelated drugs such as [[substituted amphetamine]]s.<ref name="pmid22537794"/><ref name="pmid20307223" /><ref name="mdpi-advanced-mass-spectrometry" />

[[Reagent testing]] can screen for the presence of modafinil in samples.<ref name="Spratley-2005"/><ref name="Reagent Tests UK-2015"/>

{| class="wikitable"
|+ Colors produced by modafinil with various reagents
|-
!RC
![[Marquis reagent|Marquis Reagent]]
![[Liebermann reagent|Liebermann]]
![[Froehde reagent|Froehde]]
|-
|Modafinil || Yellow/Orange > Brown<ref name="Spratley-2005"/><ref name="Reagent Tests UK-2015"/> || Darkening Orange<ref name="Spratley-2005">{{cite journal | vauthors = Spratley TK, Hayes PA, Geer LC, Cooper SD, McKibben TD | title = Analytical Profiles for Five "Designer" Tryptamines | journal = Microgram Journal | volume = 3 | issue = 1–2 | pages = 54–68 | year = 2005 | format = PDF | url = http://www.erowid.org/library/periodicals/microgram/microgram_journal_2005-1.pdf#page=54 | access-date = December 18, 2015 | archive-date = August 2, 2020 | archive-url = https://web.archive.org/web/20200802180946/https://www.erowid.org/library/periodicals/microgram/microgram_journal_2005-1.pdf#page=54 | url-status = live }}</ref> || Deep orange/red<ref name="Reagent Tests UK-2015">{{cite web | url=http://www.reagent-tests.uk/blog/modafinil-reaction-with-the-froehde-reagent-and-others/ | title=Modafinil reaction with the Froehde reagent and others | publisher=Reagent Tests UK | date=December 13, 2015 | access-date=December 18, 2015 | archive-date=August 3, 2020 | archive-url=https://web.archive.org/web/20200803124145/https://www.reagent-tests.uk/blog/modafinil-reaction-with-the-froehde-reagent-and-others/ | url-status=live }}</ref>
|}

===Structural analogs===
{{See also|List of modafinil analogues and derivatives}}

Many [[chemical derivative|derivative]]s and [[structural analog]]s of modafinil have been synthesized.<ref name="pmid32927246"/><ref name="pmid18954992">{{cite journal | vauthors = De Risi C, Ferraro L, Pollini GP, Tanganelli S, Valente F, Veronese AC | title = Efficient synthesis and biological evaluation of two modafinil analogues | journal = Bioorganic & Medicinal Chemistry | volume = 16 | issue = 23 | pages = 9904–9910 | date = December 2008 | pmid = 18954992 | doi = 10.1016/j.bmc.2008.10.027 }}</ref><ref name="pmid24494745">{{cite journal | vauthors = Okunola-Bakare OM, Cao J, Kopajtic T, Katz JL, Loland CJ, Shi L, Newman AH | title = Elucidation of structural elements for selectivity across monoamine transporters: novel 2-[(diphenylmethyl)sulfinyl]acetamide (modafinil) analogues | journal = Journal of Medicinal Chemistry | volume = 57 | issue = 3 | pages = 1000–1013 | date = February 2014 | pmid = 24494745 | pmc = 3954497 | doi = 10.1021/jm401754x }}</ref> Examples include [[adrafinil]], [[CE-123]], [[fladrafinil]] (CRL-40941; fluorafinil), [[flmodafinil]] (CRL-40940; bisfluoromodafinil, lauflumide), [[RDS03-94]], [[JJC8-088]], [[modafiendz]] and [[modafinil sulfone]] (CRL-41056).<ref name="pmid33024436">{{cite journal | vauthors = Napoletano F, Schifano F, Corkery JM, Guirguis A, Arillotta D, Zangani C, Vento A | title = The Psychonauts' World of Cognitive Enhancers | journal = Frontiers in Psychiatry | volume = 11 | pages = 546796 | date = 2020 | pmid = 33024436 | pmc = 7516264 | doi = 10.3389/fpsyt.2020.546796 | doi-access = free | title-link = doi }}</ref><ref name="pmid32927246"/>