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Substance Name: Amitriptyline [INN:BAN]
RN: 50-48-6
UNII: 1806D8D52K
InChIKey: KRMDCWKBEZIMAB-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

Molecular Weight

  • 277.409
 

Classification Codes

  • Adrenergic Agents
  • Adrenergic Uptake Inhibitors
  • Analgesics
  • Analgesics, Non-Narcotic
  • Antidepressive Agents
  • Antidepressive Agents, Tricyclic
  • Antihistaminic
  • Central Nervous System Agents
  • Drug / Therapeutic Agent
  • Human Data
  • Membrane Transport Modulators
  • Neurotransmitter Agents
  • Neurotransmitter Uptake Inhibitors
  • Peripheral Nervous System Agents
  • Psychotropic Drugs
  • Reproductive Effect
  • Sensory System Agents

Names and Synonyms

Name of Substance

  • Amitriptyline
  • Amitriptyline [INN:BAN]

MeSH Heading

  • Amitriptyline

Synonyms

  • 10,11-Dihydro-5-(gamma-dimethylaminopropylidene)-5H-dibenzo(a,d)cycloheptene
  • 10,11-Dihydro-N,N-dimethyl-5H-dibenzo(a,d)heptalene-delta(sup 5),gamma-propylamine
  • 3-(10,11-Dihydro-5H-dibenzo(a,d)cyclohepten-5-yliden)-N,N-dimethylpropylamin
  • 3-(10,11-Dihydro-5H-dibenzo(a,d)cyclohepten-5-ylidene)-N,N-dimethyl-1-propanamine
  • 5-(3'-Dimethylaminopropylidene)-dibenzo-(a,d)(1,4)-cycloheptadiene
  • 5-(3-Dimethylaminopropylidene)-10,11-dihydro-5H-dibenzo(a,d)cycloheptene
  • 5-(gamma-Dimethylaminopropylidene)-10,11-dihydro-5H-dibenzo(a,d)cycloheptene
  • 5-(gamma-Dimethylaminopropylidine)-5H-dibenzo(a,d)(1,4)cycloheptadiene
  • 5H-Dibenzo(a,d)cycloheptene-delta5,gamma-propylamine, 10,11-dihydro-N,N-dimethyl-
  • Adepress
  • Adepril
  • Amitriptilina
  • Amitriptilina [INN-Spanish]
  • Amitriptilina [Italian]
  • Amitriptylin
  • Amitriptylin [German]
  • Amitriptyline
  • Amitriptylinum
  • Amitriptylinum [INN-Latin]
  • Amytriptylin
  • BRN 2217885
  • CCRIS 9174
  • Damilen
  • Damitriptyline
  • EC 200-041-6
  • EINECS 200-041-6
  • Elavil
  • Flavyl
  • HSDB 3007
  • Lantron
  • MK 230
  • N 750
  • Proheptadiene
  • Redomex
  • Ro 4-1575
  • Seroten
  • Triptanol
  • Triptilin
  • Triptisol
  • Tryptanol
  • Tryptizol
  • UNII-1806D8D52K

Systematic Names

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

Registry Numbers

CAS Registry Number

  • 50-48-6

FDA UNII

  • 1806D8D52K

Related Registry Numbers

  • 17086-03-2 (pamoate (2:1))
  • 30227-34-0 (maleate (1:1))
  • 549-18-8 (hydrochloride)

System Generated Number

  • 0000050486

Structure Descriptors

InChI

1S/C20H23N/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

InChIKey

KRMDCWKBEZIMAB-UHFFFAOYSA-N

Smiles

C1(\c2c(CCc3c1cccc3)cccc2)=C\CCN(C)C

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
child TDLo oral 4500ug/kg (4.5mg/kg) BEHAVIORAL: SLEEP British Medical Journal. Vol. 3, Pg. 663, 1967.
dog LDLo subcutaneous 50mg/kg (50mg/kg) PERIPHERAL NERVE AND SENSATION: SPASTIC PARALYSIS WITH OR WITHOUT SENSORY CHANGE

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)
Pharmacologist. Vol. 11, Pg. 283, 1969.
guinea pig LDLo intravenous 35mg/kg (35mg/kg)   Drugs of the Future. Vol. 8, Pg. 949, 1983.
human TDLo oral 2mg/kg/3D-I (2mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

BEHAVIORAL: CHANGES IN PSYCHOPHYSIOLOGICAL TESTS
British Journal of Clinical Pharmacology. Vol. 49, Pg. 118, 2000.
human TDLo oral 14mg/kg (14mg/kg) CARDIAC: OTHER CHANGES Proceedings of the European Society for the Study of Drug Toxicity. Vol. 6, Pg. 171, 1965.
infant TDLo oral 50mg/kg (50mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)

CARDIAC: CHANGE IN RATE
American Journal of Diseases of Children. Vol. 130, Pg. 507, 1976.
man LDLo oral 29mg/kg (29mg/kg)   Human & Experimental Toxicology. Vol. 9, Pg. 257, 1990.
man TDLo oral 1564mg/kg/2Y- (1564mg/kg) PERIPHERAL NERVE AND SENSATION: PARESTHESIS

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

BEHAVIORAL: ATAXIA
Italian Journal of Neurological Sciences. Vol. 9, Pg. 89, 1988.
man TDLo unreported 45mg/kg/21D (45mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

CARDIAC: CHANGE IN RATE
Lancet. Vol. 2, Pg. 1202, 1972.
mouse LD50 intraperitoneal 48400ug/kg (48.4mg/kg)   Farmakologiya i Toksikologiya Vol. 53(4), Pg. 19, 1990.
mouse LD50 intravenous 16mg/kg (16mg/kg) BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) Journal of Medicinal Chemistry. Vol. 17, Pg. 65, 1974.
mouse LD50 oral 99mg/kg (99mg/kg)   Doklady Akademii Nauk SSSR. Proceedings of the Academy of Sciences of the USSR. For English translation, see DBIOAM and DKBSAS. Vol. 335, Pg. 388, 1994.
mouse LD50 subcutaneous 100mg/kg (100mg/kg)   United States Patent Document. Vol. #4605673,
mouse LD50 unreported 80mg/kg (80mg/kg) AUTONOMIC NERVOUS SYSTEM: "SMOOTH MUSCLE RELAXANT (MECHANISM UNDEFINED, SPASMOLYTIC)" Journal of Medicinal Chemistry. Vol. 10, Pg. 418, 1967.
rabbit LD50 intraperitoneal 58700ug/kg (58.7mg/kg) LUNGS, THORAX, OR RESPIRATION: CYANOSIS Journal of Toxicology, Clinical Toxicology. Vol. 19, Pg. 321, 1982.
rabbit LD50 intravenous 8600ug/kg (8.6mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 15, Pg. 863, 1965.
rat LD50 intraperitoneal 72mg/kg (72mg/kg)   Polish Journal of Pharmacology and Pharmacy. Vol. 27, Pg. 503, 1975.
rat LD50 oral 320mg/kg (320mg/kg) GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS

BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

BEHAVIORAL: ATAXIA
Arzneimittel-Forschung. Drug Research. Vol. 15, Pg. 863, 1965.
women TDLo intramuscular 240ug/kg/36H- (0.24mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD Lancet. Vol. 1, Pg. 390, 1968.
women TDLo oral 13500ug/kg/3D (13.5mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: EXCITEMENT
Lancet. Vol. 1, Pg. 390, 1968.
women TDLo oral 16800ug/kg/2W (16.8mg/kg) PERIPHERAL NERVE AND SENSATION: PARESTHESIS

BEHAVIORAL: HEADACHE
Lancet. Vol. 1, Pg. 426, 1968.
women TDLo oral 18500ug/kg (18.5mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

CARDIAC: EKG CHANGES NOT DIAGNOSTIC OF ABOVE

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 35, Pg. 795, 1993.
women TDLo oral 60mg/kg (60mg/kg) VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION

CARDIAC: ARRHYTHMIAS (INCLUDING CHANGES IN CONDUCTION)

CARDIAC: CHANGE IN RATE
Journal of Toxicology, Clinical Toxicology. Vol. 19, Pg. 67, 1982.
women TDLo oral 84mg/kg (84mg/kg) CARDIAC: EKG CHANGES NOT DIAGNOSTIC OF ABOVE Japanese Journal of Toxicology. Vol. 5, Pg. 69, 1992.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 196.5 deg C   EXP
pKa Dissociation Constant 9.4 (none)   EXP
log P (octanol-water) 4.92 (none)   EXP
Water Solubility 9.71 mg/L 24 EXP
Vapor Pressure 1.84E-06 mm Hg 25 EST
Henry's Law Constant 6.85E-08 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 1.79E-10 cm3/molecule-sec 25 EST

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