3-(10,11-Dihydro-5H-dibenzo(a,d)-cyclohepten-5-yliden)-N,N-dime-thyl-1-propanamin-hydrochlorid

Bezeichnung:3-(10,11-Dihydro-5H-dibenzo(a,d)-cyclohepten-5-yliden)-N,N-dime-thyl-1-propanamin-hydrochlorid

CAS-Nr549-18-8

Englisch Name:Amitriptyline hydrochloride

CBNumberCB1252307

SummenformelC20H24ClN

Molgewicht313.86

MOL-Datei549-18-8.mol

Synonyma

Amitriptylinhydrochlorid

3-(10,11-Dihydro-5H-dibenzo(a,d)-cyclohepten-5-yliden)-N,N-dime-thyl-1-propanamin-hydrochlorid

3-(10,11-Dihydro-5H-dibenzo(a,d)-cyclohepten-5-yliden)-N,N-dime-thyl-1-propanamin-hydrochlorid physikalisch-chemischer Eigenschaften

Schmelzpunkt	196-197°C
Flammpunkt	11 °C
storage temp.	2-8°C
Löslichkeit	H₂O: soluble
Aggregatzustand	powder
pka	9.4(at 25℃)
Farbe	white to off-white
PH	4.5～6.0 (10g/l, 25℃)
Wasserlöslichkeit	almost transparency
Merck	14,487
BCS Class	1
CAS Datenbank	549-18-8(CAS DataBase Reference)
EPA chemische Informationen	Amitriptyline hydrochloride (549-18-8)

Sicherheit

Kennzeichnung gefährlicher	T,F,N,Xn
R-Sätze:	23/24/25-36/37/38-42/43-63-39/23/24/25-11-50/53-36-22
S-Sätze:	22-26-36/37/39-45-36/37-16-61-60-7
RIDADR	UN 2811 6.1/PG 3
WGK Germany	3
RTECS-Nr.	HO9450000
TSCA	Yes
HazardClass	6.1(b)
PackingGroup	III
HS Code	29214990
Toxizität	LD50 in mice, rats (mg/kg): 350, 380 orally; 65, 75 i.p. (Tobe)

Gefahreninformationscode (GHS)

Amitriptyline hydrochloride Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R23/24/25:Giftig beim Einatmen, Verschlucken und Berührung mit der Haut.
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
R42/43:Sensibilisierung durch Einatmen und Hautkontakt möglich.
R63:Kann das Kind im Mutterleib möglicherweise schädigen.
R39/23/24/25:Giftig: ernste Gefahr irreversiblen Schadens durch Einatmen, Berührung mit der Haut und durch Verschlucken.
R11:Leichtentzündlich.
S-Sätze Betriebsanweisung:
S22:Staub nicht einatmen.
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36/37/39:Bei der Arbeit geeignete Schutzkleidung,Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
S45:Bei Unfall oder Unwohlsein sofort Arzt zuziehen (wenn möglich, dieses Etikett vorzeigen).
S36/37:Bei der Arbeit geeignete Schutzhandschuhe und Schutzkleidung tragen.
S16:Von Zündquellen fernhalten - Nicht rauchen.
Beschreibung
Amitriptyline (hydrochloride) (CRM) (Item No. 19031) is a certified reference material categorized as a tricyclic antidepressant. This product is intended for analytical forensic applications. This product is also available as a general research tool .
Chemische Eigenschaften
White to Off-White Solid
Originator
Elavil HCl Merck Sharp and,Dohme,US,1961
Verwenden
Amitriptyline hydrochloride is a tricyclic antidepressant drug. Amitriptyline hydrochloride inhibits the norepinephrine and serotonin transporters but has a high affinity for α1-adrenergic, serotonin and muscarinic acetylcholine receptors.
Verwenden
Amitriptyline hydrochloride has been used:
- as an antidepressant to study its effects on social behavior and memory in transgenic for acid sphingomyelinase (t-ASM) mice
- as a tricyclic antidepressant to analyze its effects on glucocorticoid receptor function in whole human blood
- as an anti-depressant to study its effects on scratching and locomotion behavior in chloroquine-induced mouse
Verwenden
vasoconstrictor
Definition
ChEBI: Amitriptyline hydrochloride is an organic tricyclic compound.
Manufacturing Process
Phthalic anhydride is reacted with phenylacetic acid to form 3- benzylidenephthalide which is then hydrogenated to 2-phenethylbenzoic acid. Conversion to the acid chloride followed by intramolecular dehydrochlorination yields the ketone, 5H-dibenzo[a,d]cyclohepten-5-one. The ketone undergoes a Grignard reaction with 3-(dimethylamino)propyl chloride to give 5-(γ- dimethylaminopropylidene)-5H-dibenzo[a,d]cycloheptene.
Then, as described in US Patent 3,205,264, a solution of 5-(γ- dimethylaminopropylidene)-5H-dibenzo[a,d]cycloheptene (42 grams; 0.153 mol) in 105 ml of ethanol is hydrogenated over Raney nickel (1.5 grams) at 65°C under an initial hydrogen pressure of 450 lb. After 1 mol of hydrogen is absorbed (3.5 hours), the reaction mixture is filtered to remove the catalyst and is acidified with 80 ml of 2.5 N hydrochloric acid (0.2 mol). The acidic solution is concentrated to dryness under vacuum and is flushed three times with 100 ml of benzene to remove residual water. The solid residue then is dried under vacuum at 40°C to yield 44.9 grams (94% of theory) of the product, MP 187-189.5°C, equivalent weight 307, ultraviolet absorption A% 2380432. Recrystallization from isopropyl alcohol and ether affords the product in high purity.
In practice it is usually used as hydrochloride.
Trademarks
Elavil (AstraZeneca); Endep (Roche).
Therapeutic Function
Antidepressant
Allgemeine Beschreibung
Amitriptyline, 3-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-N,N-dimethyl-1-propanamine hydrochloride,5-(3-dimethylaminopropylidene)-10,11-dihydro-5Hdibenzo[a,d]cycloheptene hydrochloride (Elavil), is one ofthe most anticholinergic and sedative of the TCAs. Becauseit lacks the ring-electron–enriching nitrogen atom ofimipramine, metabolic inactivation mainly proceeds not at theanalogous 2-position but at the benzylic 10-position (i.e.,toluene-like metabolism predominates). Because of the 5-exocyclic double bond, E- and Z-hydroxy isomers are producedby oxidation metabolism. Conjugation produces excretablemetabolites. As is typical of the dimethyl compounds,N-demethylation occurs, and nortriptyline is produced, whichhas a less anticholinergic, less sedative, and more stimulantaction than amitriptyline. Nortriptyline is a SNERI; thecomposite action of drug and metabolite is nonselective.
Biochem/physiol Actions
Tricyclic antidepressant; inhibits the norepinephrine and serotonin transporters with Kis of 100 nM and 14.7 nM, respectively; high in vitro affinity for α1-adrenoceptors, serotonin and muscarinic acetylcholine receptors.
Clinical Use
Tricyclic antidepressant:
Depression, used especially where sedation is required
Neuropathic pain (unlicensed)
Migraine prophylaxis (unlicensed)
Sicherheitsprofil
Poison by ingestion, intraperitoneal, intravenous, and subcutaneous routes. Human systemic effects by ingestion: convulsions, respiratory depression, changes in sleep, hallucinations, muscle contractions, somnolence, blood pressure decrease, coma, cyanosis, dyspnea, and ataxia. An experimental teratogen. Other experimental reproductive effects. Mutation data reported. Used in the treatment of depression. When heated to decomposition it emits very toxic fumes of HCl and NOx. See also ELAVIL.
Veterinary Drugs and Treatments
Amitriptyline has been used for behavioral conditions such as separation anxiety or generalized anxiety in dogs, and excessive grooming, spraying and anxiety in cats. Amitriptyline may be useful for adjunctive treatment of pruritus, or chronic pain of neuropathic origin in dogs and cats. In cats, it potentially could be useful for adjunctive treatment of lower urinary tract disease. Amitriptyline has been tried to reduce feather plucking in birds.
Arzneimittelwechselwirkung
Potentially hazardous interactions with other drugs
Alcohol: increased sedative effect.
Analgesics: increased risk of CNS toxicity with tramadol; possibly increased risk of side effects with nefopam; possibly increased sedative effects with opioids.
Anti-arrhythmics: increased risk of ventricular arrhythmias with amiodarone - avoid; increased risk of ventricular arrhythmias with disopyramide, flecainide or propafenone; avoid with dronedarone.
Antibacterials: increased risk of ventricular arrhythmias with moxifloxacin and delamanid - avoid with moxifloxacin.
Anticoagulants: may alter anticoagulant effect of coumarins.
Antidepressants: possibly increased serotonergic effects with duloxetine; enhanced CNS excitation and hypertension with MAOIs and moclobemide; concentration possibly increased with SSRIs; risk of ventricular arrhythmias with citalopram and escitalopram - avoid; possible increased risk of convulsions with vortioxetine; concentration reduced by St John’s wort.
Antiepileptics: convulsive threshold lowered; concentration reduced by carbamazepine, phenobarbital and possibly fosphenytoin, phenytoin and primidone.
Antimalarials: avoid with artemether/lumefantrine and piperaquine with artenimol.
Antipsychotics: increased risk of ventricular arrhythmias especially with droperidol, fluphenazine, haloperidol, pimozide, sulpiride and zuclopenthixol - avoid; increased antimuscarinic effects with clozapine and phenothiazines; concentration increased by antipsychotics.
Antivirals: increased risk of ventricular arrhythmias with saquinavir - avoid; concentration possibly increased with ritonavir.
Atomoxetine: increased risk of ventricular arrhythmias and possibly convulsions.
Beta-blockers: increased risk of ventricular arrhythmias with sotalol.
Clonidine: tricyclics antagonise hypotensive effect; increased risk of hypertension on clonidine withdrawal.
Cytotoxics: increased risk of ventricular arrhythmias with arsenic trioxide.
Dapoxetine: possibly increased risk of serotonergic effects - avoid. Dopaminergics: avoid with entacapone; CNS toxicity reported with selegiline and rasagiline.
Pentamidine: increased risk of ventricular arrhythmias.
Sympathomimetics: increased risk of hypertension and arrhythmias with adrenaline and noradrenaline; metabolism possibly inhibited by methylphenidate.
Stoffwechsel
Amitriptyline undergoes extensive first-pass metabolism and is demethylated in the liver by the cytochrome P450 isoenzymes CYP3A4, CYP2C9, and CYP2D6 to its primary active metabolite, nortriptyline. Other paths of metabolism of amitriptyline include hydroxylation (possibly to active metabolites) by CYP2D6 and N-oxidation; nortriptyline follows similar paths. Amitriptyline is excreted in the urine, mainly in the form of its metabolites, either free or in conjugated form.
Lager
Room temperature (desiccate)

Amitriptyline hydrochloride Upstream-Materialien And Downstream Produkte

3-(10,11-Dihydro-5H-dibenzo(a,d)-cyclohepten-5-yliden)-N,N-dime-thyl-1-propanamin-hydrochlorid Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

549-18-8, Amitriptyline hydrochloride Verwandte Suche:

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