Butriptyline

Title: Butriptyline
CAS Registry Number: 35941-65-2
CAS Name: 10,11-Dihydro-N,N,b-trimethyl-5H-dibenzo[a,d]cycloheptene-5-propanamine
Additional Names: 5-(3-dimethylamino-2-methylpropyl)-10,11-dihydro-5H-dibenzo[a,d]cycloheptene; 5-(2-methyl-3-dimethylaminopropyl)dibenzo[a,d][1,4]cycloheptadiene; butriptylene
Molecular Formula: C21H27N
Molecular Weight: 293.45
Percent Composition: C 85.95%, H 9.27%, N 4.77%
Literature References: Prepn: Winthrop, Davis, BE 613750 (1962 to Ayerst, McKenna & Harrison), C.A. 57, 15036c (1962); eidem, J. Org. Chem. 27, 230 (1962); Villani, US 3409640 (1968 to Schering). Review of pharmacology and clinical data: see J. Med. 2, 249-343 (1971). Metabolic studies: Cameron et al., Arzneim.-Forsch. 24, 93 (1974). Toxicity: Voith, Herr, Arch. Int. Pharmacodyn. Ther. 182, 318 (1969).
Properties: Oil, bp1 180-185°.
Boiling point: bp1 180-185°
Derivative Type: Hydrochloride
CAS Registry Number: 5585-73-9
Manufacturers' Codes: AY-62014
Trademarks: Evadene (Ayerst); Evadyne (Ayerst)
Molecular Formula: C21H27N.HCl
Molecular Weight: 329.91
Percent Composition: C 76.45%, H 8.55%, N 4.25%, Cl 10.75%
Properties: Crystals from isopropyl alcohol-ether, mp 188-190° (dec). uv max (methanol): 273, 270, 266 nm (e 460, 441, 552). Freely sol in water; moderately sol in aliphatic alc, chloroform. Insol in ether, paraffinic hydrocarbons. LD50 in mice (mg/kg): 120 i.p.; 345 orally (Voith, Herr).
Melting point: mp 188-190° (dec)
Absorption maximum: uv max (methanol): 273, 270, 266 nm (e 460, 441, 552)
Toxicity data: LD50 in mice (mg/kg): 120 i.p.; 345 orally (Voith, Herr)
Therap-Cat: Antidepressant.
Keywords: Antidepressant; Tricyclics.
Butropium Bromide Butyl Carbitol? Butyl Cellosolve? Butyl Citrate Butyl Isocyanate

Butriptyline
Butriptyline.svg
Systematic (IUPAC) name
(±)-3-(10,11-dihydro-5H-dibenzo[a,d]cycloheptene-5-yl)-N,N,2-trimethylpropan-1-amine
Clinical data
Legal status Prescription only
Routes Oral
Pharmacokinetic data
Half-life 20 hours
Identifiers
CAS number 35941-65-2 YesY
ATC code N06AA15
PubChem CID 21772
ChemSpider 20462 YesY
UNII Z22441975X YesY
KEGG D07601 YesY
Chemical data
Formula C21H27N 
Mol. mass 293.446 g/mol
 YesY (what is this?)  (verify)

Butriptyline (Evadene, Evadyne, Evasidol, Centrolese) is a tricyclic antidepressant (TCA) which has been used in Europe since 1974.[1][2][3][4][5] It is the isobutyl side chain homologue of amitriptyline and produces similar effects to it, but with less marked side effects like sedation and interactions with adrenergic drugs.[1][5][6]

In vitro, butriptyline is a strong antihistamine and anticholinergic, moderate 5-HT2 and α1-adrenergic receptor antagonist, and weak serotonin reuptake inhibitor, with negligible affinity for the norepinephrine and dopamine transporters.[7][8][9] These actions appear to confer a profile similar to that of iprindole and trimipramine with serotonin-blocking effects as the predominant mediator of mood-lifting efficacy.[10][11][12]

However, in clinical trials, using similar doses, butriptyline was found to be even more effective than amitriptyline as an antidepressant, despite the fact that amitriptyline is much, much stronger as both a 5-HT2 antagonist and serotonin-norepinephrine reuptake inhibitor.[7][8][9][13] As a result, it can be inferred that butriptyline, in vivo, may function as a prodrug to a metabolite with more appreciable pharmacodynamics.