Doxylamine

Doxylamine
Clinical data
Trade names	Unisom, Vicks Formula 44 (in combination with Dextromethorphan), others
AHFS/Drugs.com	Monograph
MedlinePlus	a682537
Pregnancy; category	AU: A; A (Briggs);
Routes of; administration	By mouth
ATC code	R06AA09 (WHO) ;
Legal status
Legal status	AU: S3 (Pharmacist only); US: OTC;
Pharmacokinetic data
Bioavailability	Oral: 24.7%; Intranasal: 70.8%
Metabolism	Hepatic (CYP2D6, CYP1A2, CYP2C9)
Elimination half-life	10–12 hours (range 7–15 hours)
Excretion	Urine (60%), feces (40%)
Identifiers
	IUPAC name (RS)-N,N-dimethyl-2-[1-phenyl-1-(pyridin-2-yl)ethoxy]ethan-1-amine;
CAS Number	469-21-6 ;
PubChem CID	3162;
IUPHAR/BPS	7171;
DrugBank	DB00366 ;
ChemSpider	3050 ;
UNII	95QB77JKPL;
KEGG	D07878 ;
ChEBI	CHEBI:51380 ;
ChEMBL	ChEMBL1004 ;
CompTox Dashboard (EPA)	DTXSID1022970 ;
ECHA InfoCard	100.006.742
Chemical and physical data
Formula	C17H22N2O
Molar mass	270.376 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES n1ccccc1C(c1ccccc1)(C)OCCN(C)C;
	InChI InChI=1S/C17H22N2O/c1-17(20-14-13-19(2)3,15-9-5-4-6-10-15)16-11-7-8-12-18-16/h4-12H,13-14H2,1-3H3 ; Key:HCFDWZZGGLSKEP-UHFFFAOYSA-N ;
	(verify)

Doxylamine, sold under the brand name Unisom among others, is an antihistamine medication which is used in the treatment of insomnia and allergies. It is also used to treat morning sickness in pregnant women in combination with pyridoxine (vitamin B₆). Doxylamine is available over-the-counter, and is used in nighttime cold medicines, such as NyQuil, as well as in pain medications containing acetaminophen and codeine, to help with sleep. The medication is taken by mouth.

Side effects of doxylamine include dizziness, drowsiness, grogginess, and dry mouth, among others.^[6]^[4] Doxylamine is an antihistamine—specifically an inverse agonist of the histamine H₁ receptor—and to a lesser extent an anticholinergic—specifically an antagonist of the muscarinic acetylcholine receptors M₁ through M₅. It is a first-generation antihistamine and crosses the blood–brain barrier into the brain, thereby producing centrally mediated sedative and hypnotic effects.

Doxylamine was first described in 1948 or 1949.^[7] Several of the first-generation antihistamines, including doxylamine, are the most widely used sleep medications in the world.^[8] Doxylamine is also a potent anticholinergic, which means it also works as a deliriant at much higher than recommended doses as a result.^[9] Its sedative and deliriant effects have led to some cases of recreational use.

^ ^a ^b Cite error: The named reference pmid12214324 was invoked but never defined (see the help page).
^ ^a ^b Cite error: The named reference KrygerRoth2010 was invoked but never defined (see the help page).
^ Cite error: The named reference pmid29671128 was invoked but never defined (see the help page).
^ ^a ^b Cite error: The named reference pmid27057416 was invoked but never defined (see the help page).
^ "New Zealand Datasheet: Doxylamine Succinate" (PDF). Medsafe, New Zealand Medicines and Medical Devices Safety Authority. 16 July 2008. Archived from the original on 22 March 2016.
^ Neubauer DN (August 2007). "The evolution and development of insomnia pharmacotherapies". Journal of Clinical Sleep Medicine. 3 (5 Suppl): S11–S15. doi:10.5664/jcsm.26930. PMC 1978321. PMID 17824496.
^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 546. ISBN 9783527607495.
^ Cite error: The named reference SimonsSimons2011 was invoked but never defined (see the help page).
^ "Doxylamine - PsychonautWiki".

[pmid12214324-1] Cite error: The named reference pmid12214324 was invoked but never defined (see the help page).

[KrygerRoth2010-2] Cite error: The named reference KrygerRoth2010 was invoked but never defined (see the help page).

[pmid29671128-3] Cite error: The named reference pmid29671128 was invoked but never defined (see the help page).

[pmid27057416-4] Cite error: The named reference pmid27057416 was invoked but never defined (see the help page).

[NZlabel-5] "New Zealand Datasheet: Doxylamine Succinate" (PDF). Medsafe, New Zealand Medicines and Medical Devices Safety Authority. 16 July 2008. Archived from the original on 22 March 2016.

[pmid17824496-6] Neubauer DN (August 2007). "The evolution and development of insomnia pharmacotherapies". Journal of Clinical Sleep Medicine. 3 (5 Suppl): S11–S15. doi:10.5664/jcsm.26930. PMC 1978321. PMID 17824496.

[Fis2006-7] Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 546. ISBN 9783527607495.

[SimonsSimons2011-8] Cite error: The named reference SimonsSimons2011 was invoked but never defined (see the help page).

[9] "Doxylamine - PsychonautWiki".

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