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Substance Name: Doxepin [INN:BAN]
RN: 1668-19-5
UNII: 5ASJ6HUZ7D
InChIKey: ODQWQRRAPPTVAG-GZTJUZNOSA-N

Note

  • A dibenzoxepin tricyclic compound. It displays a range of pharmacological actions including maintaining adrenergic innervation. Its mechanism of action is not fully understood, but it appears to block reuptake of monoaminergic neurotransmitters into presynaptic terminals. It also possesses anticholinergic activity and modulates antagonism of histamine H(1)- and H(2)-receptors.

Molecular Formula

  • C19-H21-N-O

Molecular Weight

  • 279.3809
 

Classification Codes

  • Antidepressive Agents
  • Antidepressive Agents, Tricyclic
  • Central Nervous System Agents
  • Drug / Therapeutic Agent
  • Histamine Agents
  • Histamine Antagonists
  • Human Data
  • Neurotransmitter Agents
  • Psychotropic Drugs
  • Sleep Aids, Pharmaceutical

Names and Synonyms

Name of Substance

  • Doxepin
  • Doxepin [INN:BAN]
  • Doxepin [USAN]

MeSH Heading

  • Doxepin

Synonyms

  • 1-Propanamine, 3-dibenz(b,e)oxepin-11(6H)-ylidene-N,N-dimethyl-
  • 11-(3-(Dimethylamino)propylidene)-6H-dibenz(b,e)oxepine
  • 11-(3-Dimethylamino-propyliden)-6,11-dihydro-dibenz(b,e)oxipin
  • 11-(3-Dimethylaminopropylidene)-6,11-dihydrodibenz(b,e)oxipin
  • CCRIS 9176
  • Doxepin
  • Doxepina
  • Doxepina [INN-Spanish]
  • Doxepine
  • Doxepinum
  • Doxepinum [INN-Latin]
  • HSDB 3069
  • MF 10
  • N,N-Dimethyldibenz(b,e)oxepin-delta(11(6H),gamma)-propylamine
  • UNII-5ASJ6HUZ7D

Systematic Names

  • 1-Propanamine, 3-dibenz(b,e)oxepin-11(6H)-ylidene-N,N-dimethyl-
  • Dibenz(b,e)oxepin-delta(sup 11(6H)),gamma-propylamine, N,N-dimethyl-

Registry Numbers

CAS Registry Number

  • 1668-19-5

FDA UNII

  • 5ASJ6HUZ7D

System Generated Number

  • 0001668195

Structure Descriptors

InChI

1S/C19H21NO/c1-20(2)13-7-11-17-16-9-4-3-8-15(16)14-21-19-12-6-5-10-18(17)19/h3-6,8-12H,7,13-14H2,1-2H3/b17-11+

InChIKey

ODQWQRRAPPTVAG-GZTJUZNOSA-N

Smiles

CN(C)CC\C=C\1/c2ccccc2COc3ccccc13

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
human LDLo oral 60mg/kg (60mg/kg) LUNGS, THORAX, OR RESPIRATION: BRONCHIECTASIS Clinical Toxicology. Vol. 10, Pg. 327, 1977.
mouse LD50 intraperitoneal 79mg/kg (79mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

AUTONOMIC NERVOUS SYSTEM: PARASYMPATHOLYTIC
Arzneimittel-Forschung. Drug Research. Vol. 15, Pg. 863, 1965.
mouse LD50 intravenous 26mg/kg (26mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

AUTONOMIC NERVOUS SYSTEM: PARASYMPATHOLYTIC
Arzneimittel-Forschung. Drug Research. Vol. 15, Pg. 863, 1965.
mouse LD50 oral 135mg/kg (135mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

AUTONOMIC NERVOUS SYSTEM: PARASYMPATHOLYTIC
Arzneimittel-Forschung. Drug Research. Vol. 15, Pg. 863, 1965.
rabbit LD50 intravenous 11mg/kg (11mg/kg) AUTONOMIC NERVOUS SYSTEM: PARASYMPATHOLYTIC

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Arzneimittel-Forschung. Drug Research. Vol. 15, Pg. 863, 1965.
rat LD50 intraperitoneal 182mg/kg (182mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

AUTONOMIC NERVOUS SYSTEM: PARASYMPATHOLYTIC
Arzneimittel-Forschung. Drug Research. Vol. 15, Pg. 863, 1965.
rat LD50 intravenous 16mg/kg (16mg/kg) AUTONOMIC NERVOUS SYSTEM: PARASYMPATHOLYTIC

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Arzneimittel-Forschung. Drug Research. Vol. 15, Pg. 863, 1965.
rat LD50 oral 147mg/kg (147mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

AUTONOMIC NERVOUS SYSTEM: PARASYMPATHOLYTIC
Arzneimittel-Forschung. Drug Research. Vol. 15, Pg. 863, 1965.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point < 25 deg C   EXP
log P (octanol-water) 4.29 (none)   EXP
Water Solubility 31.6 mg/L 25 EXP
Vapor Pressure 1.59E-06 mm Hg 25 EST
Henry's Law Constant 2.77E-09 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 1.98E-10 cm3/molecule-sec 25 EST

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