521-78-8 Usage
Description
Trimipramine Maleate Salt, also known as Surmontil, is a white crystalline solid with a chiral carbon due to the replacement of hydrogen with an -methyl substituent. It is used as a racemic mixture and shares similar biological properties with imipramine.
Uses
Used in Pharmaceutical Industry:
Trimipramine Maleate Salt is used as an antidepressant for treating depressive disorders. It functions as a serotonin transport blocker, which also inhibits the uptake of norepinephrine, leading to an improvement in mood and reduction of depressive symptoms.
Additionally, Trimipramine Maleate Salt is used as a noradrenaline uptake inhibitor, further contributing to its antidepressant effects by increasing the levels of noradrenaline in the brain, which is essential for mood regulation and overall mental well-being.
Originator
Surmontil Wyeth-Ayerst,Laboratories
Manufacturing Process
Bis(3-dimethylamino-2-methylpropyl)-5-iminodibenzylyl carboxylic acid at
185-250°C up to discontinue a separation of oxyde carbonique. The product
was dissolved in ether, then washed with the hydrochloric acid. Then this
solution was extracted with ether. The solvent was evaporated under vacuum,
to give pure oil bis(3-dimethylamino-2-methyl-1-propyl)-5-iminodibenzyle with
boiling point 153-154°C at 0.4 mm. Maleate of bis(3-dimethylamino-2-methyl-
1-propyl)-5-iminodibenzyle have melting point 145-146°C.
Therapeutic Function
Antidepressant
Biological Activity
trimipramine (maleate) is a potent antagonist of histamine h1 receptor, serotonin 5-ht2a, and α1-adrenergic receptors [1].the histamine h1 receptor is widely expressed tissues, such as smooth muscles, vascular endothelial cells, heart, and the central nervous system. histamine h1 receptor (h1r) antagonists are very effective drugs alleviating the symptoms of allergic reactions [2]. 5-ht2a receptor shows constitutive activity. variations in5-ht2a receptor can produce profound alterations in cognitive states [3]. the adrenergic receptors play an important role in modulating sympathetic nervous system activity as well as a site of action for many therapeutic agents. the α1-adrenergic receptor is the prime mediators of smooth muscle contraction and hypertrophic growth. the α1-adrenergic receptor plays an essential role in smooth muscle, growth, neurological, and cardiovascular function [4].trimipramine (maleate) is a tricyclic antidepressant compound that antagonizes several types of neurotransmitter receptors. trimipramine potently antagonized the activity of histamine h1 serotonin 5-ht2a, and α1-adrenergic receptors with the kd value of 0.27 nm, 24 nm, and 24 nm, respectively. trimipramine moderately antagonized the activity of dopamine d2 with the kd of 180 nm. trimipramine inhibited the activity of muscarinic acetylcholine with the kd of 58 nm. trimipramine weakly inhibited the activity of 5-ht2c, d1, α2-adrenergic receptors (kd = 680 nm) [1]. trimipramine (maleate) was a weak to moderate reuptake inhibitor of serotonin (ki = 149 nm for sert), and an extremely weak inhibitor of norepinephrine (ki = 2.5 μm for net) and dopamine (ki = 3.8 μm for dat) reuptake in slices of rat cerebral cortex [5,6].
Biochem/physiol Actions
Antidepressant; serotonin transport blocker that also blocks norepinephrine uptake.
references
[1] richelson e, nelson a. antagonism by antidepressants of neurotransmitter receptors of normal human brain in vitro[j]. journal of pharmacology and experimental therapeutics, 1984, 230(1): 94-102.[2] shimamura t, shiroishi m, weyand s, et al. structure of the human histamine h1 receptor complex with doxepin[j]. nature, 2011, 475(7354): 65-70.[3] harvey j a. role of the serotonin 5-ht2a receptor in learning[j]. learning & memory, 2003, 10(5): 355-362.[4] piascik m t, perez d m. α1-adrenergic receptors: new insights and directions[j]. journal of pharmacology and experimental therapeutics, 2001, 298(2): 403-410.[5] gross g, xie x, gastpar m. trimipramine: pharmacological reevaluation and comparison with clozapine[j]. neuropharmacology, 1991, 30(11): 1159-1166.[6] tatsumi m, groshan k, blakely r d, et al. pharmacological profile of antidepressants and related compounds at human monoamine transporters[j]. european journal of pharmacology, 1997, 340(2): 249-258.
Check Digit Verification of cas no
The CAS Registry Mumber 521-78-8 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,2 and 1 respectively; the second part has 2 digits, 7 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 521-78:
(5*5)+(4*2)+(3*1)+(2*7)+(1*8)=58
58 % 10 = 8
So 521-78-8 is a valid CAS Registry Number.
InChI:InChI=1/C20H26N2.C4H4O4/c1-16(14-21(2)3)15-22-19-10-6-4-8-17(19)12-13-18-9-5-7-11-20(18)22;5-3(6)1-2-4(7)8/h4-11,16H,12-15H2,1-3H3;1-2H,(H,5,6)(H,7,8)/b;2-1-