Tripelennamine HCl (Pyrinamine; Stanzamine; Tripelennamine; Pyribenzamine), the hydrochloride salt of Tripelennamine, is a potent histamine H1 receptor antagonist that has been widely used as an antipruritic agent. It functions by preventing PhIP glucuronidation at an IC50 of 30 μM.
Physicochemical Properties
| Molecular Formula | C16H22CLN3 | |
| Molecular Weight | 291.82 | |
| Exact Mass | 291.15 | |
| Elemental Analysis | C, 65.85; H, 7.60; Cl, 12.15; N, 14.40 | |
| CAS # | 154-69-8 | |
| Related CAS # | Tripelennamine; 91-81-6; Tripelennamine citrate; 6138-56-3 | |
| PubChem CID | 9066 | |
| Appearance | White to off-white solid powder | |
| Density | 1.20 | |
| Boiling Point | 387.8ºC at 760 mmHg | |
| Melting Point | 192-193ºC | |
| Flash Point | 188.3ºC | |
| Vapour Pressure | 3.21E-06mmHg at 25°C | |
| LogP | 3.451 | |
| Hydrogen Bond Donor Count | 1 | |
| Hydrogen Bond Acceptor Count | 3 | |
| Rotatable Bond Count | 6 | |
| Heavy Atom Count | 20 | |
| Complexity | 236 | |
| Defined Atom Stereocenter Count | 0 | |
| SMILES | Cl[H].N(C1=C([H])C([H])=C([H])C([H])=N1)(C([H])([H])C1C([H])=C([H])C([H])=C([H])C=1[H])C([H])([H])C([H])([H])N(C([H])([H])[H])C([H])([H])[H] |
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| InChi Key | FSSICIQKZGUEAE-UHFFFAOYSA-N | |
| InChi Code | InChI=1S/C16H21N3.ClH/c1-18(2)12-13-19(16-10-6-7-11-17-16)14-15-8-4-3-5-9-15;/h3-11H,12-14H2,1-2H3;1H | |
| Chemical Name | N'-benzyl-N,N-dimethyl-N'-pyridin-2-ylethane-1,2-diamine;hydrochloride | |
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| 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. |
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| 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 | H1 receptor ( IC50 = 30 μM ) | ||
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| References |
[1]. H1-receptor antagonist, tripelennamine, does not affect arterial hypoxemia in exercising Thoroughbreds. J Appl Physiol. 2002 Apr;92(4):1515-23. [2]. Comparative disposition of tripelennamine in horses and camels after intravenous administration. J Vet Pharmacol Ther. 2000 Jun;23(3):145-52. [3]. The pharmacokinetics of pentazocine and tripelennamine. Clin Pharmacol Ther. 1986 Jun;39(6):669-76. |
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| Additional Infomation |
Tripelenamine hydrochloride appears as odorless white crystalline powder or solid. Bitter taste. Solutions are neutral to litmus. pH of aqueous solution (25 mg/mL): 6.71. pH of aqueous solution (50 mg/mL): 6.67. pH of aqueous solution (100 mg/mL): 5.56. (NTP, 1992) Tripelennamine Hydrochloride is the hydrochloride salt form of tripelennamine, an ethylenediamine derivative with an antihistaminergic property. Tripelennamine hydrochloride competitively blocks central and peripheral histamine H1 receptors, thereby limiting histamine's effects, including bronchoconstriction, vasodilation, increased capillary permeability, and spasmodic contractions of gastrointestinal smooth muscle. In addition, this agent binds to muscarinic receptors, resulting in anticholinergic activity. A histamine H1 antagonist with low sedative action but frequent gastrointestinal irritation. It is used to treat ASTHMA; HAY FEVER; URTICARIA; and RHINITIS; and also in veterinary applications. Tripelennamine is administered by various routes, including topically. See also: Tripelennamine (has active moiety). |
Solubility Data
| Solubility (In Vitro) |
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (8.57 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 (8.57 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 (8.57 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: 33.33 mg/mL (114.21 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 | 3.4268 mL | 17.1338 mL | 34.2677 mL | |
| 5 mM | 0.6854 mL | 3.4268 mL | 6.8535 mL | |
| 10 mM | 0.3427 mL | 1.7134 mL | 3.4268 mL |