Molecular Structure:

Molecular Formula: C₂₀H₂₃N
Molecular Weight: 277.4033
IUPAC Name: (3S,4R)-3-(1,3-Benzodioxol-5-yloxymethyl)-4-(4-fluorophenyl)piperidine
Synonyms of Amitriptyline (CAS NO.50-48-6): 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] ; Amitriptylinum ; Amitriptylinum [INN-Latin] ; Amytriptylin ; BRN 2217885 ; CCRIS 9174 ; Damilen ; Damitriptyline ; EINECS 200-041-6 ; Elavil ; Flavyl ; Lantron ; MK 230 ; N 750 ; Proheptadiene ; Redomex ; Ro 4-1575 ; Seroten ; Triptanol ; Triptilin ; Triptisol ; Tryptanol ; UNII-1806D8D52K ; 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-
CAS NO: 50-48-6
Classification Code: Adrenergic Agents ; Adrenergic uptake inhibitors ; Analgesics ; Analgesics, Non-Narcotic ; Antidepressive Agents ; Antidepressive agents, tricyclic ; Antihistaminic ; Central Nervous System Agents ; Drug / Therapeutic Agent ; Human Data ; Neurotransmitter Agents ; Neurotransmitter Uptake Inhibitors ; Peripheral Nervous System Agents ; Psychotropic Drugs ; Reproductive Effect ; Sensory System Agents
Melting point: 196-197°C 
Index of Refraction: 1.628
Molar Refractivity: 91.52 cm³
Molar Volume: 257.7 cm³
Surface Tension: 47 dyne/cm
Density: 1.076 g/cm³
Flash Point: 174 °C
Enthalpy of Vaporization: 64.88 kJ/mol
Boiling Point: 398.2 °C at 760 mmHg
Vapour Pressure: 1.5E-06 mmHg at 25°C

  Amitriptyline (CAS NO.50-48-6) is recommended for the treatment of mental depression, with improvement in mood seen in 2 to 3 weeks after the start of medication. It is now used in the United States and United Kingdom to prevent migraines only in very small doses. It is also used as sleeping aids in small doses of usually 25 mg, and for diabetic retinopathy.

The synthesis of Amitriptyline (CAS NO.50-48-6) starts from the key intermediate dibenzo-suberone (manufactured from phthalic anhydride) and can proceed by two pathways (Fig. 1). Treatment of dibenzosuberone with cyclopropyl Grignard gives the tertiary alcohol after hydrolysis. Reaction of the alcohol with hydrochloric acid proceeds with rearrangement and opening of the strained cyclopropane to give a chloride. Reaction and displacement of the chlorine atom with dimethylamine forms amitriptyline. Alternatively, dibenzosuberone can be reacted with dimethylaminopropyl Grignard to form an alcohol, which upon dehydration forms amitriptyline.

FIGURE 1 Manufacture of amitriptyline.

Human poison by an unspecified route. Poison experimentally by ingestion, intraperitoneal, subcutaneous, intramuscular, and intravenous routes. Human systemic effects by ingestion and intramuscular routes: changes in sleep, headache, paresthesia, convulsions, excitement, somnolence, muscle contractions, change in heart rate, and other cardiac changes. An experimental teratogen. Other experimental reproductive effects. An antidepressant. When heated to decomposition it emits toxic fumes of NO_x.

Common side effects of using amitriptyline are mostly due to its anticholinergic activity, including: weight gain, dry mouth, loss of appetite, drowsiness, muscle stiffness, nausea, constipation, nervousness, dizziness, blurred vision, urinary retention and insomnia. Some rare side effects include tinnitus, hypotension, mania, psychosis, heart block, arrhythmias, lip and mouth ulcers, extrapyramidal symptoms, depression, and hepatic toxicity.