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HCID 4976Erstellt: 4. November 2026

N-Methyl-5H-dibenzo(a,d)cyclohep-ten-5-propanamin

Triptil · Vivactil · Amimetilina · Protriptylin · PROTRIPTYLINE · Protryptyline · Protriptyline-d6 · Protriptyline 13CD3

https://huagongshe.com/de/chemical/4976

Molekülstruktur von N-Methyl-5H-dibenzo(a,d)cyclohep-ten-5-propanamin

Identifikatoren & physikalische Daten

CAS No.438-60-8
SummenformelC19H21N
Durchschnittliche Molmasse263,4 g/mol
Monoisotopische Masse263,16739967 g/mol
SMILESCNCCCC1c2ccccc2C=Cc2ccccc21
InChIKeyBWPIARFWQZKAIA-UHFFFAOYSA-N
PubChem CID4976
ChEMBLCHEMBL668
ChEBICHEBI:8597
EC No.207-119-9
DTXSIDDTXSID0023535
Lokaler NameN-Methyl-5H-dibenzo(a,d)cyclohep-ten-5-propanamin

Chemische & physikalische Eigenschaften

XLogP4,4
Polarare Oberfläche (TPSA)12
H-Brücken-Donoren1
H-Brücken-Akzeptoren1
Frei drehbare Bindungen4
Schwere Atome20
Formalladung0
Komplexität296
ArzneimittelDEA NFLIS-Drug Category -> StimulantsPharmaceuticals -> Listed in ZINC15
LogP (Verteilungskoeffizient)log Kow= 1.18 @ 25 °C4.7
LöslichkeitSOL: 1 G IN ABOUT 2 ML WATER, ABOUT 2 ML METHANOL, ABOUT 2.3 ML CHLOROFORM, ABOUT 4 ML ALCOHOLPRACTICALLY INSOL IN ETHER /HYDROCHLORIDE/Freely sol in water /hydrochloride/2.31e-04 g/L
Human DrugsAntidepressants -> Tricyclic antidepressants (TCA)Breast FeedingLactationMilk, HumanAntidepressive AgentsAntidepressive Agents, TricyclicPharmaceuticals
Endocrine DisruptorsPotential endocrine disrupting compound
DecompositionWhen heated to decomposition it emits toxic fumes of nitroxides.
Schmelzpunkt169-171 °C (Protriptyline HCl)Max absorption 290 nm (e= 13,311)MP: 169-171 °Ccrystals from isopropanol- ethyl ether /hydrochloride/169 - 171 °C (protriptyline hydrochloride)
Physical DescriptionSolid
Stability/Shelf LifeREASONABLY STABLE IN LIGHT, STABLE IN AIR, & STABLE IN HEAT UNDER USUAL PREVAILING TEMP /HYDROCHLORIDE/
Collision Cross Section164.5 Ų [M+H]+ [CCS Type: DTBuffer gas: N2Ionization: ESI+Dataset: Antidepressants]162.8 Ų [M+H]+ [CCS Type: TWMethod: Major Mix IMS/Tof Calibration Kit (Waters)]Method: calibrated with polyalanine and drug standards]161.47 Ų [M+H]+ [CCS Type: TW
Other Experimental PropertiesODORLESS OR HAS NOT MORE THAN SLIGHT ODOR & HAS BITTER TASTEWHITE TO YELLOWISH POWDER /HYDROCHLORIDE/
Siedepunkt396.62°C (rough estimate)
Dichte0.9076 (rough estimate)
Brechungsindex1.7500 (estimate)
pKa (Säurekonstante)8.2(at 25℃)
EPA chemische InformationenProtriptyline (438-60-8)

Sicherheit & Vorschriften

Regulatorische Informationen5H-Dibenzoa,dcycloheptene-5-propanamine, N-methyl-: Does not have an individual approval but may be used under an appropriate group standard
FDA-AnforderungenManufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended21 U.S.C. 321-392).
EntsorgungsverfahrenSRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
TreatmentDry mouth, if severe to the point of causing difficulty speaking or swallowing, may be managed by dosage reduction or temporary discontinuation of the drug. Patients may also chew sugarless gum or suck on sugarless candy in order to increase the flow of saliva. Some artificial saliva products may give temporary relief. Men with prostate enlargement who take protriptyline may be especially likely to have problems with urinary retention. Symptoms include having difficulty starting a urine flow and more difficulty than usual passing urine. In most cases, urinary retention is managed with dose reduction or by switching to another type of antidepressant. In extreme cases, patients may require treatment with bethanechol, a drug that reverses this particular side effect. As management of overdose is complex and changing, it is recommended that the physician contact a poison control center for current information on treatment. Signs and symptoms of toxicity develop rapidly after tricyclic antidepressant overdose, therefore, hospital monitoring is required as soon as possible. (Wikipedia)
WechselwirkungenOther interactions that also may potentiate the effects of tricyclic antidepressants can result from interference with their metabolism in the liver. This effect has been associated with neuroleptic drugs, methylphenidate, and certain steroids, including oral contraceptives. /Tricyclic antidepressants/TRICYCLIC ANTIDEPRESSANTS MAY ENHANCE EFFECTS OF ORAL ANTICOAGULANTS. /TRICYCLIC ANTIDEPRESSANTS/A PARTICULARLY SEVERE, BUT RARE, DRUG-DRUG INTERACTION HAS BEEN NOTED FOLLOWING THE CONCURRENT ADMINISTRATION OF AN MAO INHIBITOR AND A TRICYCLIC ANTIDEPRESSANT. /TRICYCLIC ANTIDEPRESSANTS/

Anwendungen & Verwendung

Verwenden

Protriptyline is a powerful antidepressant, the mechanism of action of which is not known. It is not a MAO inhibitor and does not stimulate the CNS. It begins to act much faster and acts much longer than imipramine or amitriptyline. Protriptyline does not possess sedative tranquilizing properties. It is used in clinical conditions for treating severe depression.

THIS AGENT IS ALSO CONTRAINDICATED IN PT TAKING ANY OF MAO INHIBITOR ANTIDEPRESSANTS, SUCH AS NIALAMIDE, ISOCARBOXAZID, TRANYLCYPROMINE, OR PHENELZINE. /HYDROCHLORIDE/
For more Interactions (Complete) data for PROTRIPTYLINE (32 total), please visit the HSDB record page.
Gesundheitliche AuswirkungenProtriptyline shares side effects common to all tricyclic antidepressants. The most frequent of these are dry mouth, constipation, urinary retention, increased heart rate, sedation, irritability, dizziness, decreased coordination, anxiety, blood disorders, confusion, decreased libido, dizziness, flushing, headache, impotence, insomnia, low blood pressure, nightmares, rapid or irregular heartbeat, rash, seizures, sensitivity to sunlight, stomach and intestinal problems. Other more complicated side effects includechest pain or heavy feeling, pain spreading to the arm or shoulder, nausea, sweating, general ill feelingsudden numbness or weakness, especially on one side of the bodysudden headache, confusion, problems with vision, speech, or balancehallucinations, or seizure (convulsions)easy bruising or bleeding, unusual weaknessrestless muscle movements in your eyes, tongue, jaw, or neckurinating less than usual or not at allextreme thirst with headache, nausea, vomiting, and weaknessor feeling light-headed or fainting. Deaths may occur from overdosage with this class of drugs. Multiple drug ingestion (including alcohol) is common in deliberate tricyclic antidepressant overdose. (Wikipedia)
HepatotoxicityLiver test abnormalities have been reported to occur in 10% to 12% of patients on tricyclic antidepressants, but elevations are uncommonly above 3 times the upper limit of normal. The aminotransferase abnormalities are usually mild, asymptomatic and transient, reversing even with continuation of medication. The rate of serum enzyme elevations specifically during protriptyline therapy has not been well defined. Rare instances of clinically apparent acute liver injury have been reported in patients on tricyclic antidepressants, but there have been no specific reports related to protriptyline. In typical tricyclic antidepressant acute liver injury, the latency to onset has ranged from 1 to 14 months. The pattern of serum enzyme elevations was typically cholestatic, but hepatocellular cases have also been reported including an acute hepatitis-like syndrome with acute liver failure. Instances of acute cholestatic hepatitis and prolonged jaundice compatible with vanishing bile duct syndrome have been linked to other tricyclic antidepressants, mostly amitriptyline and imipramine, the two most commonly used agents in this class. Signs or symptoms of hypersensitivity (rash, fever and eosinophilia) are frequent in reported cases, but these symptoms are usually mild and transient. Autoantibody formation is rare. Protriptyline is a rarely used tricyclic antidepressant but is suspected of having a profile of adverse effects similar to that of imipramine and amitriptyline.
Unerwünschte WirkungenProtriptyline, like all TCAs, has multiple adverse effects. Although as effective as SSRIs and SNRIs, TCAs, and MAOs are not first-line treatment due to their side effects. Among the TCAs, protriptyline is the most likely to cause tachycardia, hypotension, anxiety, and agitation, and for this reason, some European countries have discontinued protriptyline use.
ExpositionspfadeOral
ToxizitätsübersichtTricyclic antidepressants, like all antidepressants, are used in a group of patients that are already at increased risk of attempted suicide. Thus, overdose with such drugs is something that needs to have a plan at hand. Furthermore, TCAs are often used in drug-resistant depression, which makes them even more of a risk than the first-line SSRIs and SNRIs. Thus protriptyline is a very potent TCA and a dangerous drug for overdose.Protriptyline acts by decreasing the reuptake of norepinephrine and serotonin (5-HT).
Signs and SymptomsWithdrawal symptoms include gastrointestinal disturbances, anxiety, and insomnia.
Human Toxicity ExcerptsOCCASIONAL PT WILL SHOW PHYSICAL DEPENDENCE ... FOLLOWING ABRUPT DISCONTINUATION OF HIGH DOSES ... /TRICYCLIC ANTIDEPRESSANTS/Effects of overdosage include agitation, hallucinations, hyperreflexia, hyperpyrexia, and convulsions. /Tricyclic antidepressants/VENTRICULAR FIBRILLATION WAS OBSERVED IN 51-YR OLD WOMAN RECEIVING PERPHENAZINE & PROTRIPTYLINE. PERPHENAZINE ALSO WIDENED VENTRICULAR ECHO ZONE & ALLOWED INDUCTION OF LONG RUNS OF VENTRICULAR TACHYCARDIA. BOTH DRUGS INCR INCIDENCE OF VENTRICULAR DYSRHYTHMIAS.EFFECTS OF AMITRIPTYLINE-HCL, NORTRIPTYLINE-HCL, & PROTRIPTYLINE HCL & BW-247 ON PERFORMANCE TESTS & SUBJECTIVE RATINGS IN 2 DOUBLE BLIND TRIALS WITH 24 VOLUNTEERS. NO SIGNIFICANT CHANGE FOLLOWED 10 MG PROTRIPTYLINE OR 12.5 & 25 MG BW-247.PROTRIPTYLINE HAD NO EFFECT ON THE EXTN FRACTION OF WATER.
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Drug Induced Liver InjuryDrug-Induced Liver Injury Severity and Toxicity (DILIst)protriptylineDILI NegativeOralDOI:10.1016/j.drudis.2019.09.022
Non-Human Toxicity ExcerptsPOS CHRONOTROPISM IN RATS @ PLASMA CONCN OF 0.04-1.2 MUG/ML@ HIGHER LEVELS POS CHRONOTROPIC EFFECT DECR & BRADYCARDIA DEVELOPED. THRESHOLD PLASMA LEVEL GIVING 40 DEG RIGHT ROTATION OF ELECTRICAL AXIS OF HEART 1.75 MUG/ML. ATRIOVENTRICULAR CONDUCTION PROLONGED @ 3.6 MUG/ML.
Gefahrstoffdaten438-60-8(Hazardous Substances Data)