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Amitriptyline

Amitriptyline Structure
Amitriptyline
  • CAS No.50-48-6
  • Chemical Name:Amitriptyline
  • CBNumber:CB1159271
  • Molecular Formula:C20H23N
  • Formula Weight:277.4
  • MOL File:50-48-6.mol
Amitriptyline Property
  • Melting point 196-197°C
  • Boiling point 410.26°C (rough estimate)
  • Density 0.9415 (rough estimate)
  • refractive index 1.7500 (estimate)
  • storage temp. Store at -20°C
  • form Liquid
  • pka 9.4(at 25℃)
  • color Colorless to light yellow
  • Water Solubility 9.7 mg/mL
  • Stability Light Sensitive
  • CAS DataBase Reference 50-48-6(CAS DataBase Reference)
  • FDA UNII 1806D8D52K
  • ATC code N06AA09
  • NIST Chemistry Reference Amitriptyline(50-48-6)
  • EPA Substance Registry System Amitriptyline (50-48-6)
Safety
Hazard and Precautionary Statements (GHS)
  • Symbol(GHS)
  • Signal wordDanger
  • Hazard statements H361-H301+H311+H331-H410-H318
  • Precautionary statements P273-P391-P501-P201-P202-P281-P308+P313-P405-P501-P280-P305+P351+P338-P310

Amitriptyline Chemical Properties,Usage,Production

  • Originator Elavil HCl Merck Sharp and,Dohme,US,1961
  • Uses Amitriptyline is used for anxious-depressive conditions. It is easier to tolerate than imipramine.
  • Uses Antidepressant.
  • Definition ChEBI: An organic tricyclic compound that is 10,11-dihydro-5H-dibenzo[a,d][7]annulene substituted by a 3-(dimethylamino)propylidene group at position 5.
  • 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.
  • brand name Elavil (AstraZeneca); Endep (Roche);Ami-anelun;Amilent;Amilit-ifi;Aminiurin;Amitimid;Amitriptol;Amyline;Amyzol;Annolytin;Apo-amitriptylline;Apo-pram;Deprelio;Deprestal;Diapatal;Elatrolet;Elavil plus;Emitrip;Enovil;Entrafon-210;Entrafon-2-10;Entrafon-2-25;Entrafon-a;Entrafon-forte;Etarfon;Etrafon-a;Etrafon-forte;Laroxal;Larozyl;Levate;Limbatarail;Limbatral;Limbitryl;Limitrol;Longopax;Loxaryl;Mareline;Meravil;Muaban d;Mutaban a/d/f;Nobrital;Novotriptyn;Novotryptin;Novo-tryptin;Parks-plus;Pms levazine;Prouvil;Saratem;Sarotena;Sedans;Sylvemid;Tensorelax;Teperin;Trepiline;Trepulin;Triptizol;Triptonal;Triptpane;Trivial-4-10.
  • Therapeutic Function Antidepressant
  • World Health Organization (WHO) Amitriptyline, a tricyclic antidepressant was introduced in 1961 for the management of endogenous depression and is listed in the 8th WHO Model List of Essential Drugs. Much of the adverse effects are caused by its antimuscarinic actions. These include dry mouth, cardiac arrhythmias, central nervous system disturbances, blood disorders and risk of suicide. The risk of suicide and dangers related to overdosage led the Norwegian Medicines Control Authority to put the higher strength formulation under prescribing restriction in 1992. The risk of death following overdosage is apparently higher for products containing tricyclic compounds as compared with nontricyclic products.
  • Biological Functions Amitriptyline is a tertiary amine dibenzocycloheptadiene TCA with a propylidene side chain extending from the central carbocyclic ring. The diarylpropylideneamine moiety for amitriptyline makes it sensitive to photo-oxidation; therefore, its hydrochloride solutions should be protected from light to avoid ketone formation and precipitation.
  • Pharmacokinetics Amitriptyline is rapidly absorbed from the GI tract and from parenteral sites.Amitriptyline and its active metabolite, nortriptyline, are distributed into breast milk. Amitriptyline is primarily (65%) metabolized by N-demethylation by CYP2D6 to nortriptyline and hydroxylation to its E-10-hydroxy metabolite. Nortriptyline is pharmacologically active as a secondary amine TCA. Amitriptyline shows approximately equal affinity for 5-HT and NE transporters.
  • Synthesis Amitriptyline, 5-(3-dimethylaminopropyliden)-10,11-dihydrodibenzocycloheptene (7.1.4), differs from imipramine in that the nitrogen atom in the central part of the tricyclic system is replaced by a carbon, which is bound to a side chain by a double bond. Amitriptyline (7.1.4) is synthesized by interaction of 10,11-dihydro-N,N-dimethyl- 5H-dibenzo[a,d]cyclohepten-5-one with 3-dimethylaminopropylmagnesium bromide and the subsequent dehydration of the resulting tertiary alcohol (7.1.3) using hydrochloric acid [6–11].
    Synthesis_50-48-6_1
    An alternative way of synthesis of amitriptyline is by interaction of 10,11-dihydro-N,Ndimethyl-5H-dibenzo[a,d]-cyclohepten-5-one with cyclopropylmagnesium bromide, giving 10,11-dihydro-N,N-dimethyl-5H-dibenzo[a,d]-cyclohepten-5-cyclopropyl-5-ol (7.1.5). Reacting this with hydrogen bromide in acetic acid results in an opening of the cyclopropyl ring, which forms 5-(3-bromopropyliden)-10,11-dihydro-5H-dibenzo[a,d]-cycloheptene (7.1.6). Alkylating this with dimethylamine gives amitriptyline (7.1.4) [12,13].
    Synthesis_50-48-6_2
Amitriptyline Preparation Products And Raw materials
Raw materials
Preparation Products
Amitriptyline Suppliers
Global(103)Suppliers
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    AFINE CHEMICALS LIMITED
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Amitriptyline Spectrum
50-48-6, AmitriptylineRelated Search:
  • 抑制剂
  • 药靶配体
  • FDA批准的配体
  • 原料药
  • 贝尔卡主打
  • 医药原料
  • 医药原料
  • 神经系统用药
  • C20H23NNa
  • C20H23N
  • C20H22N
  • 阿米替林检测标准品
  • 1-甲基-6-氧代-1
  • 6-二氢吡啶-3-羧酸
  • 盐酸去甲替林EP杂质F
  • 3-(10,11-二氢-5H-二苯并[A,D]环庚烯-5-亚基)-N,N-二甲基丙基-1-胺
  • 阿米替林 50-48-6
  • 3-(10,11-二氢-5H-二苯并[a,d]环庚烯-5-亚基)-N,N-二甲基-1-丙胺
  • 阿密曲替林
  • 阿米替林溶液, 100PPM
  • 阿米替林
  • 50-48-6
  • 3-(10,11-dihydro-5H-dibenzo[a,d][7]annulen-5-ylidene)-N,N-dimethylpropan-1-amine (amitriptyline)
  • Amitryptyline
  • Amitryptiline
  • Amitriptylin
  • amitriptilina
  • Elavil
  • 5-(3-dimethylaminopropylidene)-10,11-dihyro-5h-dibenzo(a,d)cycloheptene
  • 5-(3-Dimethylaminopropylidene)-10,11-dihydro-5H-dibenzo(a,d)cycloheptatriene
  • 6-dihydropyridine-3-carboxylic acid
  • 1-Methyl-6-oxo-1
  • Amitriptyline USP/EP/BP
  • 3-(5,6-DIHYDRODIBENZO[2,1-B:2',1'-F][7]ANNULEN-11-YLIDENE)-N,N-DIMETHYLPROPAN-1-AMINE
  • MK-230, N-750, Ro41575
  • Amitriptyline (base and/or unspecified salts)
  • DIBENZOSUBERONE /AMITRIPTYLINE
  • AMITRIPTHYLINE
  • [3-(10,11-DIHYDRO-DIBENZO[A,D]CYCLOHEPTEN-5-YLIDENE)-PROPYL]-DIMETHYL-AMINE
  • 3-(10,11-dihydro-5h-dibenzo[a,d]cyclohepten-5-ylidene)-n,n-dimethyl-1-propanamine
  • 3-(10,11-dihydro-5H-dibenzo[a,d][7]annulen-5-ylidene)-N,N-diMethylpropan-1-aMine
  • 3-(10,11-Dihydro-5H-dibenzo[a,d][7]annulen-5-ylidene)-N,N-dimethyl-1-propanamine
  • Larxyl
  • Tryptizol
  • Tryptanol
  • Triptisol
  • Triptanol
  • Seroten
  • sarotex
  • ro4-1575
  • Ro 4-1575
  • redomex
  • 1-Propanamine, 3-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-N,N-dimethyl-
  • 10,11-Dihydro-N,N-dimethyl-5H-dibenzo(a,d)heptalene-delta<sup>5</sup>,gamma-propylamine
  • 10,11-dihydro-n,n-dimethyl-5h-dibenzo(a,d)heptalene-delta(sup5),gamma-propyl
  • 10,11-Dihydro-5-(gamma-dimethylaminopropylidene)-5H-dibenzo(a,d)cycloheptene
  • AMITRYPTYLLINE NA
  • AMITRIPTYLINE

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