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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
- All
- Classifications
- Links to Resources
- Names & Synonyms
- Registry Numbers
- Structure Descriptors
- Toxicity
- Physical Properties
Classification Codes
- Adrenergic Agents
- Adrenergic Uptake Inhibitors
- Analgesics
- Analgesics, Non-Narcotic
- Antidepressive Agents
- Antidepressive Agents, Tricyclic
- Antihistaminic
- Antiviral (COVID-19)
- 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
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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
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,7,13-15H2,1-2H3InChIKey
KRMDCWKBEZIMAB-UHFFFAOYSA-NSmiles
CN(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.