CAS 469-21-6

(±)-Doxylamine

Description:

(±)-Doxylamine is an antihistamine belonging to the ethanolamine class, primarily used for its sedative and anti-allergic properties. It is a racemic mixture, meaning it contains equal parts of two enantiomers, which can exhibit different biological activities. The substance is typically encountered as a white to off-white crystalline powder, and it is soluble in water and alcohol, making it suitable for various formulations. Doxylamine acts by blocking the H1 histamine receptors, thereby alleviating symptoms of allergies and providing relief from insomnia due to its sedative effects. It is commonly found in over-the-counter sleep aids and cold medications. The compound has a relatively low toxicity profile when used as directed, but it can cause side effects such as drowsiness, dry mouth, and dizziness. Due to its sedative properties, caution is advised when operating machinery or driving after consumption. Overall, (±)-Doxylamine is a versatile compound with applications in both allergy relief and sleep management.

Formula: C₁₇H₂₂N₂O

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

InChI key: InChIKey=HCFDWZZGGLSKEP-UHFFFAOYSA-N

SMILES: C(OCCN(C)C)(C)(C1=CC=CC=C1)C2=CC=CC=N2

Synonyms:

• (.+-.)-Doxylamine
• 2-[α-[2-(Dimethylamino)ethoxy]-α-methylbenzyl]pyridine
• Donormil
• Doxilminio
• Doxylamin
• Ls 127
• N,N-Dimethyl-2-[1-phenyl-1-(2-pyridinyl)ethoxy]ethanamine
• Pyridine, 2-[α-[2-(dimethylamino)ethoxy]-α-methylbenzyl]-
• Ethanamine, N,N-dimethyl-2-[1-phenyl-1-(2-pyridinyl)ethoxy]-
• dimethyl(2-(1-phenyl-1-(2-pyridyl)ethoxy)ethyl)amine
• alpha-Dimethylaminoethoxyphenylmethyl-2-picoline
• 2-(alpha-(2-(Dimethylamino)ethoxy)-alpha-methylbenzyl)pyridine
• Phenyl-2-pyridylmethyl-beta-N,N-dimethylaminoethyl ether
• phenyl-2-pyridylmethyl-b-N,N-dimethylaminoethyl ether
• Pyridine, 2-[alpha-[2-(dimethylamino)ethoxy]-alpha-methylbenzyl]-
• DOXYLAMINE USP/EP/BP
• 2-dimethylaminoethoxyphenylmethyl-2-picoline
• NCI C60684
• oxylamine
• Doxylamine Hydrogen inate

Doxylamine Succinate

CAS: 469-21-6, 562-10-7

Formula: C₁₇H₂₂N₂O·C₄H₆O₄

Purity: >98.0%(T)(HPLC)

Color and Shape: White to Almost white powder to crystal

Molecular weight: 388.46

Ref: 3B-D5583

Doxylamine

CAS: 469-21-6

Formula: C₁₇H₂₂N₂O

Molecular weight: 270.38

Ref: 4Z-D-385

S-Doxylamine

Controlled Product

CAS: 469-21-6

Applications S-Doxylamine is a first-​generation antihistamine and a sedative. Doxylamine is used to treat nausea and vomiting of pregnancy. Overdose of Doxylamine can cause rhabdomyolysis.
References Cantrell, F.L., et al.: Clin. Toxicol., 53, 178 (2015); Choi, H., et al.: Yakhak Hoechi, 59, 230 (2015); Koren, G., et al.: BMC Pregnancy Childbirth, 15, 1 (2015); Jo, Y., et al.: Hum Exp Toxicol., 26, 617 (2007)

Formula: C₁₇H₂₂N₂O

Color and Shape: Neat

Molecular weight: 270.37

Ref: TR-D562035

(±)-Doxylamine

Controlled Product

CAS: 469-21-6

Stability Temperature Sensitive
Applications (±)-Doxylamine is an intermediate in the synthesis of Doxylamine N, N’-Dioxide (D562025), which is an impurity of Doxylamine (succinate salt, D562000), which is an H1 Histamine receptor antagonist.
References Sjoqvist, F., et al.: Clin. Pharmacol. Ther., 8, 48 (1967), Eccles, R., et al.: J. Pharm. Pharmacol., 47, 990 (1995)

Formula: C₁₇H₂₂N₂O

Color and Shape: Neat

Molecular weight: 270.37

Ref: TR-D562005