Binedaline

Title: Binedaline
CAS Registry Number: 60662-16-0
CAS Name: N,N,N¢-Trimethyl-N¢-(3-phenyl-1H-indol-1-yl)-1,2-ethanediamine
Additional Names: 1-[[2-(dimethylamino)ethyl]methylamino]-3-phenylindole; binodaline
Molecular Formula: C19H23N3
Molecular Weight: 293.41
Percent Composition: C 77.78%, H 7.90%, N 14.32%
Literature References: Norepinephrine reuptake inhibitor with antidepressant activity. Prepn: F. Schatz et al., DE 2512702; eidem, US 4204998 (1975, 1980 both to Siegfried); eidem, Arzneim.-Forsch. 30, 919 (1980). Mechanism of action study: D. P. Benfield, D. K. Luscombe, ibid. 33, 847 (1983). Pharmacology, toxicity: U. Jahn et al., ibid. 726. Biochemical studies: J. Maj et al., ibid. 841. Binding to human plasma proteins: D. Morin et al., J. Pharm. Sci. 74, 727 (1985). Clinical pharmacology: P. H. Joubert et al., Eur. J. Clin. Pharmacol. 27, 667 (1985).
Properties: Crystals from petroleum, mp 52-53°.
Melting point: mp 52-53°
Derivative Type: Hydrochloride
CAS Registry Number: 57647-35-5
Manufacturers' Codes: RU-39780; Sgd-Scha-1059
Molecular Formula: C19H23N3.HCl
Molecular Weight: 329.87
Percent Composition: C 69.18%, H 7.33%, N 12.74%, Cl 10.75%
Properties: Colorless crystals from isopropanol, mp 195-196°. uv max (0.1N HCl): 222, 263 nm (e 28000, 14500). LD50 in male, female mice, male, female rats (mg/kg): 760, 770, 1380, 1160 orally; 54.0, 54.0, 27.2, 26.0 i.v. (Jahn).
Melting point: mp 195-196°
Absorption maximum: uv max (0.1N HCl): 222, 263 nm (e 28000, 14500)
Toxicity data: LD50 in male, female mice, male, female rats (mg/kg): 760, 770, 1380, 1160 orally; 54.0, 54.0, 27.2, 26.0 i.v. (Jahn)
Status: This monograph has been retired and is no longer subject to revision or update.
Binifibrate Binodenoson Biocytin Bioflavonoids Biopterin

Binedaline
Binedaline.png
Systematic (IUPAC) name
N,N,N-trimethyl-N-(3-phenylindol-1-yl)ethane-1,2-diamine
Clinical data
Legal status Uncontrolled
Routes Oral
Identifiers
CAS number 60662-16-0 N
ATC code None
PubChem CID 42509
ChemSpider 38769 YesY
UNII 3AVG9P140R YesY
Chemical data
Formula C19H24ClN3 
Mol. mass 329.86696 g/mol
 N (what is this?)  (verify)

Binedaline (Ixprim), also called binodaline, is a drug that was being investigated as an antidepressant in the 1980s but never marketed.[1][2] It acts as a selective norepinephrine reuptake inhibitor (Ki = 25 nM), with relatively insignificant influence on the serotonin (Ki = 847 nM) and dopamine (Ki >= 2 µM) transporters.[3] It has negligible affinity for the α-adrenergic, mACh, H1, or 5-HT2 receptors.[3]