Skip Navigation
ChemIDplus A TOXNET DATABASE LiteBrowseAdvanced

Substance Name: Amitriptyline hydrochloride [USP:JAN]
RN: 549-18-8
UNII: 26LUD4JO9K
InChIKey: KFYRPLNVJVHZGT-UHFFFAOYSA-N

Note

  • Tricyclic antidepressant with anticholinergic and sedative properties. It appears to prevent the re-uptake of norepinephrine and serotonin at nerve terminals, thus potentiating the action of these neurotransmitters. Amitriptyline also appears to antagonize cholinergic and alpha-1 adrenergic responses to bioactive amines.

Molecular Formula

  • C20-H23-N.Cl-H

Molecular Weight

  • 313.8696
 

Classification Codes

  • Antidepressant
  • Drug / Therapeutic Agent
  • Human Data
  • Mutation Data
  • Reproductive Effect

Names and Synonyms

Name of Substance

  • Amitriptyline hydrochloride
  • Amitriptyline hydrochloride [USP:JAN]

Synonyms

  • 1-Propanamine, 3-(10,11-dihydro-5H-dibenzo(a,d)cyclohepten-5-ylidene)-N,N-dimethyl-, hydrochloride
  • 10,11-Dihydro-N,N-dimethyl-5H-dibenzo(a,d)cycloheptene-delta(sup 5,gamma)-propylamine hydrochloride
  • 5-(3-Dimethylaminopropylidene)dibenzo(a,d)(1,4)cycloheptadiene hydrochloride
  • Adepril
  • ADT-Zimaia
  • Amavil
  • Ami-Anelun
  • Amilit
  • Amineurin
  • Amiplin
  • Amiprin
  • Amitid
  • Amitril
  • Amitrip
  • Amitriptyline chloride
  • Amitriptyline HCl
  • Amitriptyline hydrochloride
  • Amyline
  • Amyzol
  • Anapsique
  • Annoyltin
  • Apo-Amitriptyline
  • Belpax
  • CCRIS 7092
  • Damilen hydrochloride
  • Daprimen
  • Deprex
  • Domical
  • EINECS 208-964-6
  • Elatrol
  • Elatrolet
  • Elavil
  • Elavil hydrochloride
  • Enafon
  • Endep
  • Etrafon
  • Etravil
  • Kyliran
  • Laroxyl
  • Larozyl
  • Lentizol
  • Levate
  • Limbitrol DS
  • Maxivalet
  • Miketorin
  • Mitaptyline
  • NIH 10794
  • Nornaln
  • Novoprotect
  • Novotriptyn
  • NSC 104210
  • Oasil-M
  • Pinsanu
  • Pinsaun
  • Proheptadien monohydrochloride
  • Rantoron
  • Redomex
  • Saroten
  • Saroten Retard
  • Sarotena
  • sk-Amitriptyline chloride
  • Syneudon
  • Teperin
  • Trepiline
  • Triavil
  • Tridep
  • Tripta
  • Triptizol
  • Trynol
  • Tryptacap hydrochloride
  • Tryptine
  • Tryptizol
  • Tryptizol retard
  • Trytomer
  • UNII-26LUD4JO9K
  • Vanatrip
  • Yamanouchi

Systematic Names

  • 1-Propanamine, 3-(10,11-dihydro-5H-dibenzo(a,d)cyclohepten-5-ylidene)-N,N-dimethyl-, hydrochloride
  • 1-Propanamine, 3-(10,11-dihydro-5H-dibenzo(a,d)cyclohepten-5-ylidene)-N,N-dimethyl-, hydrochloride (1:1)
  • 5H-Dibenzo(a,d)cycloheptene-delta(sup 5),gamma-propylamine, 10,11-dihydro-N,N-dimethyl-, hydrochloride
  • 5H-Dibenzo(a,d)cycloheptene-delta5,gamma-propylamine, 10,11-dihydro-N,N-dimethyl-, hydrochloride (8CI)
  • Amitriptyline hydrochloride

Mixture Names

  • Etrafon
  • Limbitrol
  • Triavil

Registry Numbers

CAS Registry Number

  • 549-18-8

FDA UNII

  • 26LUD4JO9K

Other Registry Number

  • 8058-15-9

Related Registry Number

  • 50-48-6 (Parent)

System Generated Number

  • 0000549188

Molecular Formulas

Molecular Formula

  • C20-H23-N.Cl-H

Molecular Formula Fragments

  • C20-H23-N
  • Cl-H
  • COMPONENT

Structure Descriptors

InChI

1S/C20H23N.ClH/c1-21(2)15-7-12-20-18-10-5-3-8-16(18)13-14-17-9-4-6-11-19(17)20;/h3-6,8-12H,7,13-15H2,1-2H3;1H

InChIKey

KFYRPLNVJVHZGT-UHFFFAOYSA-N

Smiles

Cl.CN(C)CCC=C1c2ccccc2CCc3ccccc13

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LD50 oral 37mg/kg (37mg/kg)   Drug Development Research. Vol. 22, Pg. 385, 1991.
child LDLo oral 62500ug/kg (62.5mg/kg) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION

VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
New England Journal of Medicine. Vol. 267, Pg. 1031, 1962.
child LDLo oral 62500ug/kg (62.5mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: CYANOSIS
American Journal of Diseases of Children. Vol. 106, Pg. 501, 1963.
child TDLo oral 4167ug/kg (4.167mg/kg) BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)

BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"

BEHAVIORAL: SLEEP
New England Journal of Medicine. Vol. 267, Pg. 1031, 1962.
child TDLo oral 58mg/kg (58mg/kg) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION

VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION

BEHAVIORAL: COMA
Southern Medical Journal. Vol. 82, Pg. 1588, 1989.
dog LD50 intramuscular > 23mg/kg (23mg/kg)   Oyo Yakuri. Pharmacometrics. Vol. 6, Pg. 899, 1972.
dog LD50 intravenous > 27mg/kg (27mg/kg)   Oyo Yakuri. Pharmacometrics. Vol. 6, Pg. 899, 1972.
dog LDLo oral 200mg/kg (200mg/kg)   Oyo Yakuri. Pharmacometrics. Vol. 6, Pg. 889, 1972.
guinea pig LDLo intravenous 52mg/kg (52mg/kg) CARDIAC: OTHER CHANGES Therapie. Vol. 20, Pg. 67, 1965.
human TDLo oral 200mg/kg (200mg/kg) BEHAVIORAL: COMA

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)
JAMA, Journal of the American Medical Association. Vol. 230, Pg. 1405, 1974.
man TDLo oral 714ug/kg/1D-I (0.714mg/kg) BEHAVIORAL: CHANGES IN PSYCHOPHYSIOLOGICAL TESTS

BEHAVIORAL: ALTERATION OF OPERANT CONDITIONING
Human Psychopharmacology. Vol. 7, Pg. 273, 1992.
man TDLo oral 14286ug/kg (14.286mg/kg) BEHAVIORAL: COMA

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Lancet. Vol. 2, Pg. 543, 1963.
man TDLo oral 60mg/kg/3W-I (60mg/kg) BEHAVIORAL: WITHDRAWAL

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: ATAXIA
Journal of Clinical Psychiatry. Vol. 53, Pg. 160, 1992.
monkey LDLo intravenous 20300ug/kg (20.3mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION
Indian Journal of Experimental Biology. Vol. 22, Pg. 539, 1984.
mouse LD50 intraperitoneal 65mg/kg (65mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Journal of Drug Research. Vol. 16, Pg. 7, 1985.
mouse LD50 intravenous 21mg/kg (21mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 21, Pg. 808, 1971.
mouse LD50 oral 140mg/kg (140mg/kg)   Wiener Medizinische Wochenschrift. Vol. 111, Pg. 256, 1961.
mouse LD50 subcutaneous 80mg/kg (80mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: ATAXIA

LUNGS, THORAX, OR RESPIRATION: CYANOSIS
Oyo Yakuri. Pharmacometrics. Vol. 6, Pg. 889, 1972.
rabbit LD50 intravenous 9900ug/kg (9.9mg/kg)   "Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972Vol. -, Pg. 61, 1972.
rat LD50 intraperitoneal 67mg/kg (67mg/kg)   Drugs in Japan Vol. -, Pg. 49, 1990.
rat LD50 intravenous 14mg/kg (14mg/kg)   "Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972Vol. -, Pg. 61, 1972.
rat LD50 oral 240mg/kg (240mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: ATAXIA

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Oyo Yakuri. Pharmacometrics. Vol. 6, Pg. 889, 1972.
rat LD50 subcutaneous 385mg/kg (385mg/kg) LUNGS, THORAX, OR RESPIRATION: CYANOSIS

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
European Journal of Pharmacology. Vol. 32, Pg. 108, 1975.
women LDLo oral 19mg/kg (19mg/kg) BEHAVIORAL: COMA

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Lancet. Vol. 2, Pg. 543, 1963.
women TDLo oral 10mg/kg (10mg/kg) BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS" Canadian Medical Association Journal. Vol. 129, Pg. 1203, 1983.