Alizapride HCl (Limican; Plitican; Vergentan; Superan; Alizaprida; Litican; MS-5080), the hydrochloride salt of alizapride which is a medication used for the theropy of nausea and vomiting, is a potent dopamine receptor antagonist with prokinetic and antiemetic effects.

Physicochemical Properties

Molecular Formula	C16H22CLN5O2
Molecular Weight	351.83
Exact Mass	351.146
Elemental Analysis	C, 54.62; H, 6.30; Cl, 10.08; N, 19.91; O, 9.09
CAS #	59338-87-3
Related CAS #	Alizapride; 59338-93-1; Alizapride-13C,d3 hydrochloride
PubChem CID	135497066
Appearance	Solid powder
Density	1.224 g/cm3
Boiling Point	580.3ºC at 760 mmHg
Melting Point	206-208°
Flash Point	304.8ºC
LogP	2.477
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	6
Heavy Atom Count	24
Complexity	433
Defined Atom Stereocenter Count	0
InChi Key	BRECEDGYMYXGNF-UHFFFAOYSA-N
InChi Code	InChI=1S/C16H21N5O2.ClH/c1-3-6-21-7-4-5-11(21)10-17-16(22)12-8-13-14(19-20-18-13)9-15(12)23-2;/h3,8-9,11H,1,4-7,10H2,2H3,(H,17,22)(H,18,19,20);1H
Chemical Name	6-methoxy-N-[(1-prop-2-enylpyrrolidin-2-yl)methyl]-3H-benzotriazole-5-carboxamide;hydrochloride
Synonyms	MS 5080; MS5080; Limican; Plitican; Vergentan; Superan; Alizaprida; Litican; MS-5080
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	Dopamine receptor
ln Vitro	In vitro activity: Alizapride has an N-allyl moiety, which means it may go through epoxidation, N-deallylation, or other reactions that lead to the formation of chemically reactive metabolites.[1]
ln Vivo	Alizapride shows little toxicity (especially when administered parenterally) in mice and rats. In rodents and mice, alipride exhibits minimal toxicity (particularly when given topically). When administered orally or intravenously, Alizapride is primarily eliminated as an unchanged medication; however, approximately 25% of the drug goes through metabolic conversion prior to elimination. In rats, the aforementioned doses of apomorphine cause a decrease in gastrointestinal transit, which is counteracted by alisparid (5 mg/kg, s.c.).[2]
Enzyme Assay	A dopamine receptor antagonist with prokinetic and antiemetic properties, alizapride hydrochloride is also used to treat nausea and vomiting, including postoperative nausea and vomiting.
Animal Protocol	Male Duncan–Hartley guinea pigs Dosage: 2.5, 5, 10, 25 μg/kg Administration: Alizapride (2.5, 5, 10, 25 μg/kg; SC; 7 consecutive days)
References	[1]. Activity of a new antiemetic agent: alizapride. A randomized double-blind crossover controlled trial. Cancer Chemother Pharmacol. 1988;22(4):316-20..
Additional Infomation	Alizapride Hydrochloride is the hydrochloride salt form of alizapride, a methoxy-2-benzamide derivative and dopamine 2 (D2) receptor antagonist, with antiemetic activity. Upon administration, alizapride binds to and blocks the D2 receptor in the chemoreceptive trigger zone (CTZ) of the medulla, thereby preventing nausea and vomiting.

Solubility Data

Solubility (In Vitro)

DMSO: 33.3~42 mg/mL (94.7~119.4 mM) Water: ~70 mg/mL (~198.95 mM) Ethanol: <1 mg/mL

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 2.5 mg/mL (7.11 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 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: ≥ 2.5 mg/mL (7.11 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in 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 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 3: ≥ 2.5 mg/mL (7.11 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (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 900 μL of corn oil and mix evenly. Solubility in Formulation 4: 50 mg/mL (142.11 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	2.8423 mL	14.2114 mL	28.4228 mL
	5 mM	0.5685 mL	2.8423 mL	5.6846 mL
	10 mM	0.2842 mL	1.4211 mL	2.8423 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.