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Substance Name: Doxepin hydrochloride [USAN:USP]
RN: 1229-29-4
UNII: 3U9A0FE9N5
InChIKey: MHNSPTUQQIYJOT-SJDTYFKWSA-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.Cl-H

Molecular Weight

  • 315.8418
 

Classification Codes

  • Antidepressant
  • Drug / Therapeutic Agent
  • Human Data
  • Reproductive Effect
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Names and Synonyms

Name of Substance

  • Doxepin hydrochloride [USAN:USP]

Synonyms

  • 1-Propanamine, 3-dibenz(b,e)oxepin-11(6H)ylidene-N,N-dimethyl-, hydrochloride
  • 11-(3-(Dimethylamino)propylidene)-6,11-dihydrodibenz(b,e)oxepin hydrochloride
  • Adapin
  • Aponal
  • Curatin
  • Doxepin HCl
  • Doxepin hydrochloride
  • Doxepine hydrochloride
  • EINECS 214-966-8
  • MF 10 HCl
  • N,N-Dimethyldibenz(b,e)oxepin-delta(sup 11(6H),gamma)-propylamine hydrochloride
  • Novoxapin
  • Novoxapin hydrochloride
  • NSC-108160
  • P-3693A
  • Quitaxon
  • Silenor
  • Sinequan
  • Sinequin
  • Toruan
  • UNII-3U9A0FE9N5
  • Zonalon

Systematic Names

  • 1-Propanamine, 3-dibenz(b,e)oxepin-11(6H)ylidene-N,N-dimethyl-, hydrochloride
  • Dibenz(b,e)oxepin-delta(sup 11(6H),gamma)-propylamine, N,N-dimethyl-, hydrochloride
  • Dibenz(b,e)oxepin-delta11(6H),gamma-propylamine, N,N-dimethyl-, hydrochloride
  • Doxepin hydrochloride

Registry Numbers

CAS Registry Number

  • 1229-29-4

FDA UNII

  • 3U9A0FE9N5

Other Registry Number

  • 20917-44-6

System Generated Number

  • 0001229294

Molecular Formulas

Molecular Formula

  • C19-H21-N-O.Cl-H

Molecular Formula Fragments

  • C19-H21-N-O
  • Cl-H
  • COMPONENT

Structure Descriptors

InChI

InChI=1S/C19H21NO.ClH/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;1H/b17-11+;

InChIKey

MHNSPTUQQIYJOT-SJDTYFKWSA-N

Smiles

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

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
child TDLo skin 75mg/kg (75mg/kg) CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP

BEHAVIORAL: SLEEP		 Annals of Pharmacotherpy. Vol. 34, Pg. 328, 2000.
dog LD50 intramuscular 40mg/kg (40mg/kg) SENSE ORGANS AND SPECIAL SENSES: MYDRIASIS (PUPILLARY DILATION): EYE

GASTROINTESTINAL: NAUSEA OR VOMITING

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD		 Oyo Yakuri. Pharmacometrics. Vol. 6, Pg. 889, 1972.
dog LD50 intravenous > 27mg/kg (27mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING

SENSE ORGANS AND SPECIAL SENSES: MYDRIASIS (PUPILLARY DILATION): EYE

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD		 Oyo Yakuri. Pharmacometrics. Vol. 6, Pg. 889, 1972.
dog LDLo oral 300mg/kg (300mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING

SENSE ORGANS AND SPECIAL SENSES: MYDRIASIS (PUPILLARY DILATION): EYE

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD		 Oyo Yakuri. Pharmacometrics. Vol. 6, Pg. 889, 1972.
human LDLo oral 90mg/kg (90mg/kg) BLOOD: HEMORRHAGE

BEHAVIORAL: COMA

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD		 Journal of Analytical Toxicology. Vol. 2, Pg. 18, 1978.
human TDLo oral 9300ug/kg (9.3mg/kg) BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)

BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"

CARDIAC: CHANGE IN RATE		 JAMA, Journal of the American Medical Association. Vol. 237, Pg. 2632, 1977.
man LDLo oral 357ug/kg (0.357mg/kg) VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION

BEHAVIORAL: MUSCLE WEAKNESS

BEHAVIORAL: COMA		 Journal of Analytical Toxicology. Vol. 7, Pg. 161, 1983.
man TDLo oral 357ug/kg (0.357mg/kg)   Australian and New Zealand Journal of Medicine. Vol. 23, Pg. 523, 1993.
man TDLo oral 357ug/kg (0.357mg/kg) LIVER: "HEPATITIS (HEPATOCELLULAR NECROSIS), ZONAL" Australian and New Zealand Journal of Medicine. Vol. 23, Pg. 523, 1993.
monkey LDLo intravenous 20400ug/kg (20.4mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)		 Indian Journal of Experimental Biology. Vol. 22, Pg. 539, 1984.
mouse LD50 intraperitoneal 79mg/kg (79mg/kg)   "Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972Vol. -, Pg. 72, 1972.
mouse LD50 intravenous 15mg/kg (15mg/kg)   "Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972Vol. -, Pg. 72, 1972.
mouse LD50 oral 180mg/kg (180mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: ATAXIA

BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)		 Oyo Yakuri. Pharmacometrics. Vol. 6, Pg. 889, 1972.
mouse LD50 subcutaneous 160mg/kg (160mg/kg)   "Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972Vol. -, Pg. 72, 1972.
rabbit LD50 intravenous 11mg/kg (11mg/kg)   "Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972Vol. -, Pg. 72, 1972.
rat LD50 intraperitoneal 84mg/kg (84mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: ATAXIA

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD		 Oyo Yakuri. Pharmacometrics. Vol. 6, Pg. 889, 1972.
rat LD50 intravenous 13mg/kg (13mg/kg)   "Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972Vol. -, Pg. 72, 1972.
rat LD50 oral 147mg/kg (147mg/kg)   "Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972Vol. -, Pg. 72, 1972.
rat LD50 subcutaneous 155mg/kg (155mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: CYANOSIS		 Oyo Yakuri. Pharmacometrics. Vol. 6, Pg. 889, 1972.
women TDLo oral 112mg/kg/4W-I (112mg/kg) BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS" Journal of Clinical Psychiatry. Vol. 44, Pg. 106, 1983.
women TDLo oral 141mg/kg/12W- (141mg/kg) SENSE ORGANS AND SPECIAL SENSES: TINNITUS: EAR Southern Medical Journal. Vol. 76, Pg. 1204, 1983.