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Substance Name: Doxylamine [INN:BAN]
RN: 469-21-6
UNII: 95QB77JKPL
InChIKey: HCFDWZZGGLSKEP-UHFFFAOYSA-N

Note

  • Histamine H1 antagonist with pronounced sedative properties. It is used in allergies and as an antitussive, antiemetic, and hypnotic. Doxylamine has also been administered in veterinary applications and was formerly used in PARKINSONISM.

Molecular Formula

  • C17-H22-N2-O

Molecular Weight

  • 270.374
 

Classification Codes

  • Antiemetics
  • Autonomic Agents
  • Central Nervous System Agents
  • Gastrointestinal Agents
  • Histamine Agents
  • Histamine Antagonists
  • Histamine H1 Antagonists
  • Neurotransmitter Agents
  • Peripheral Nervous System Agents

Names and Synonyms

Name of Substance

  • Doxylamine
  • Doxylamine [INN:BAN]

MeSH Heading

  • Doxylamine

Synonyms

  • 2-(alpha-(2-(Dimethylamino)ethoxy)-alpha-methylbenzyl)pyridine
  • 2-Dimethylaminoethoxyphenylmethyl-2-picoline
  • 5-21-03-00508 (Beilstein Handbook Reference)
  • BRN 0230379
  • Dossilamina
  • Dossilamina [DCIT]
  • Doxilminio
  • Doxilminio [INN-Spanish]
  • Doxylamine
  • Doxylaminum
  • Doxylaminum [INN-Latin]
  • EC 207-414-2
  • EINECS 207-414-2
  • HSDB 5184
  • N,N-Dimethyl-2-(1-phenyl-1-(2-pyridinyl)ethoxy)ethanamine
  • NCI C60684
  • Phenyl-2-pyridylmethyl-beta-N,N-dimethylaminoethyl ether
  • Pyridine, 2-(alpha-(2-(dimethylamino)ethoxy)-alpha-methylbenzyl)-
  • UNII-95QB77JKPL

Systematic Names

  • Doxylamine
  • Ethanamine, N,N-dimethyl-2-(1-phenyl-1-(2-pyridinyl)ethoxy)-

Superlist Name

  • Doxylamine

Registry Numbers

CAS Registry Number

  • 469-21-6

FDA UNII

  • 95QB77JKPL

System Generated Number

  • 0000469216

Structure Descriptors

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

InChIKey

HCFDWZZGGLSKEP-UHFFFAOYSA-N

Smiles

c1([C@@](c2ccccn2)(OCCN(C)C)C)ccccc1

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
man TDLo oral 57mg/kg (57mg/kg) BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"

BEHAVIORAL: MUSCLE WEAKNESS

BEHAVIORAL: COMA
Toxicology Letters. Vol. 109(Suppl,
mouse LD50 intravenous 62mg/kg (62mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD Dangerous Properties of Industrial Materials Report. Vol. 2(5), Pg. 17, 1982.
mouse LD50 oral 470mg/kg (470mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD Dangerous Properties of Industrial Materials Report. Vol. 2(5), Pg. 17, 1982.
mouse LD50 subcutaneous 460mg/kg (460mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD Dangerous Properties of Industrial Materials Report. Vol. 2(5), Pg. 17, 1982.
rabbit LD50 intravenous 49mg/kg (49mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: REGIDITY
Dangerous Properties of Industrial Materials Report. Vol. 2(5), Pg. 17, 1982.
rabbit LD50 oral 250mg/kg (250mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: REGIDITY
Dangerous Properties of Industrial Materials Report. Vol. 2(5), Pg. 17, 1982.
rat LD50 subcutaneous 440mg/kg (440mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD Dangerous Properties of Industrial Materials Report. Vol. 2(5), Pg. 17, 1982.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point < 25 deg C   EXP
log P (octanol-water) 2.370 (none)   EST
Atmospheric OH Rate Constant 1.12E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.