Citalopram Hydrobromide (Lu-10-171) is a potent and FDA approved antidepressant drug of the selective serotonin reuptake inhibitor (SSRI) class. In control rats, the mono- and polysynaptic reflex amplitudes were reduced to approximately 40–50% of the preadministration value 15 minutes after cyclobenzaprine was administered. It is prescribed off-label for various conditions and has been used to treat major depression. Citalopram hydrobromide acts as a selective inhibitor of serotonin reuptake, meaning that it increases serotonergic activity in the central nervous system by selectively inhibiting the reuptake of serotonin by CNS neurons.

Physicochemical Properties

Molecular Formula	C20H22BRFN2O
Molecular Weight	405.3039
Exact Mass	404.089
Elemental Analysis	C, 59.27; H, 5.47; Br, 19.71; F, 4.69; N, 6.91; O, 3.95
CAS #	59729-32-7
Related CAS #	Citalopram; 59729-33-8; 207559-01-1 (oxalate); 59729-32-7 (HBr)
PubChem CID	77995
Appearance	White to off-white solid powder
Boiling Point	182-188ºC
Melting Point	182-188ºC
Flash Point	212.8ºC
LogP	4.771
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	5
Heavy Atom Count	25
Complexity	466
Defined Atom Stereocenter Count	0
SMILES	Br[H].FC1C([H])=C([H])C(=C([H])C=1[H])C1(C2C([H])=C([H])C(C#N)=C([H])C=2C([H])([H])O1)C([H])([H])C([H])([H])C([H])([H])N(C([H])([H])[H])C([H])([H])[H]
InChi Key	WIHMBLDNRMIGDW-UHFFFAOYSA-N
InChi Code	InChI=1S/C20H21FN2O.BrH/c1-23(2)11-3-10-20(17-5-7-18(21)8-6-17)19-9-4-15(13-22)12-16(19)14-24-20;/h4-9,12H,3,10-11,14H2,1-2H3;1H
Chemical Name	1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-3H-2-benzofuran-5-carbonitrile;hydrobromide
Synonyms	Lu10-171-BLu-10-171-BCelexa Cipramil Citalopram HBr HSDB 7042 EINECS 261-890-6 Lu 10-171-B CPD000326936
HS Tariff Code	2934.99.9001
Storage	Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: Please store this product in a sealed and protected environment, avoid exposure to moisture.
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity

Targets	serotonin reuptake ( IC50 = 1.8 nM )
ln Vitro	Citalopram (Lu 10-171), an exceptionally strong inhibitor of neuronal serotonin (5-HT) uptake, a novel bicyclic phthalane derivative exhibits no antagonistic activity toward 5-HT, histamine, gamma aminobutyric acid (GABA), acetylcholine, and morphine receptors, and has no effect on the uptake of noradrenaline (NA) or dopamine (DA). It is a very strong and selective inhibitor of the uptake of 5-HT by neurons. The medication has no effect on the uptake mechanisms for other transmitter amines[1]. The effects of the SSRI citalopram are more pronounced on proliferation and less pronounced on apoptotic activity. By enhancing proliferative potential and lowering apoptotic activity in a site-specific manner that may be suggestive of hyperplasia, it influences the regulation of the cell cycle. In osteoblast cell culture, citalopram modifies the expression of FGF, MSX, and TGFB[3].
ln Vivo	Citalopram even when administered in quantities well above the therapeutic range, has no cardiotoxic effects on the animals. Citabram is metabolized in humans to produce substances that are less abundant than citalopram itself but are nevertheless strong 5-HT-uptake inhibitors without affecting noradrenaline (NA) uptake. Citalopram (1–16 mg/kg) causes the spinal rat's hindlimb flexor reflex to fire. Citalopram may increase the amount of 5-HT transmitted by causing marked uptake inhibition without also inhibiting the post-synaptic 5-HT receptors1.
Cell Assay	Eagles medium (alpha minimum) supplemented with 10% fetal bovine serum, 1% penicillin/streptomycin, and amphotericin B is used to cultivate the cells. The standard alpha proliferation media is used to culture the cells for a duration of 3 or 7 days, providing control data. A dose response curve is obtained for SSRI treatments by supplementing media with citalopram eluted to serially diluted doses between 10−4 mol and 10−10 mol.
Animal Protocol	Spontaneously Hypertensive rats (SHRs), Lewis (LEW) rats, and Wistar-Kyoto (WKY) rats 1-10 mg/kg i.p.
References	[1]. Prog Neuropsychopharmacol Biol Psychiatry . 1982;6(3):277-95. [2]. Neuropsychopharmacology . 2000 Jan;22(1):64-76. [3]. PLoS One . 2015 Oct 2;10(10):e0139719.
Additional Infomation	Citalopram Hydrobromide is the orally bioavailable hydrobromide salt of the racemic bicyclic phthalene derivative citalopram with antidepressant activity. As a selective serotonin reuptake inhibitor (SSRI), citalopram selectively inhibits the CNS neuronal reuptake of serotonin, thereby potentiating serotonergic activity in the central nervous system (CNS). This agent has minimal effects on the CNS neuronal reuptake of norepinephrine (NE) and dopamine (DA). A furancarbonitrile that is one of the SELECTIVE SEROTONIN REUPTAKE INHIBITORS used as an antidepressant. The drug is also effective in reducing ethanol uptake in alcoholics and is used in depressed patients who also suffer from TARDIVE DYSKINESIA in preference to tricyclic antidepressants, which aggravate dyskinesia. See also: Citalopram (has active moiety).

Solubility Data

Solubility (In Vitro)

DMSO: ~81 mg/mL (~199.9 mM) Water: ~81 mg/mL Ethanol: ~81 mg/mL

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 2.5 mg/mL (6.17 mM) (saturation unknown) in 10% DMSO + 40% PEG300 +5% Tween-80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 + to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: 110 mg/mL (271.40 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with ultrasonication.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	2.4673 mL	12.3365 mL	24.6731 mL
	5 mM	0.4935 mL	2.4673 mL	4.9346 mL
	10 mM	0.2467 mL	1.2337 mL	2.4673 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.