13492-01-8 Usage
Description
Tranylcypromine (13492-01-8) is an irreversible and non-selective monoamine oxidase inhibitor.1,2?It has been shown to inhibit the histone demethylase BHC110/LSD1.3,4
Chemical Properties
A white or almost white, crystalline powder.
Uses
Monoamine oxidase inhibitor; antidepressant.
Therapeutic Function
Psychostimulant
General Description
Tranylcypromine sulfate, (±)-trans-2-phenylcyclopropylaminesulfate (Parnate), was synthesized to be an amphetamineanalog (visualize the α-methyl of amphetaminecondensed onto the β-carbon atom).It does have someamphetamine-like properties, which may be why it has moreimmediate CNS-stimulant effects than agents that act byMAO inhibition alone. For MAO inhibition, there may betwo components to the action of this agent. One is thoughtto arise because tranylcypromine has structural features (thebasic nitrogen and the quasi-π character of the α- andβ-cyclopropane carbon atoms) that approximate the transitionstate in a route of metabolism of β-arylamines. As α-and β-hydrogen atoms are removed from the normal substrateof the enzyme, the quasi-π character develops over theα,β-carbon system. Duplication of the transition state permitsextremely strong, but reversible, attachment to the enzyme.Additionally, tranylcypromine is a mechanism-based inactivator.It is metabolized by MAO, with one electron of the nitrogenpair lost to flavin. This, in turn, produces homolyticfission of a carbon–carbon bond of cyclopropane, with oneelectron from the fission pairing with the remaining lone nitrogenelectron to generate an imine (protonated) and with theother residing on a methylene carbon. Thus, a free radical isformed that reacts to form a covalent bond with the enzymeor with reduced flavin to inactivate the enzyme.
References
1) Knoll?et al. (1980),?Monoamine oxidase inhibitors: Chemistry and Pharmacology; In, Sandler (ed) Enzyme inhibitors as drugs, MacMillan, London 151
2) Baker?et al. (1992),?Insights into the mechanisms of action of the MAO inhibitors phenelzine and tranylcypromine; a review, J.Psychiatry Neurosci.?17?206
3) Lee?et al. (2006),?Histone H3 lysine 4 demethylation is a target of nonselective antidepressive medications; Chemistry and Biology,?13?563
4) Schmidt and McCafferty (2007),?trans-2-Phenylcyclopropylamine is a Mechanism-Based Inactivator of the Histone Demethylase LSD1; Biochemistry,?46?4408
Check Digit Verification of cas no
The CAS Registry Mumber 13492-01-8 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,3,4,9 and 2 respectively; the second part has 2 digits, 0 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 13492-01:
(7*1)+(6*3)+(5*4)+(4*9)+(3*2)+(2*0)+(1*1)=88
88 % 10 = 8
So 13492-01-8 is a valid CAS Registry Number.
InChI:InChI=1/C9H11N.H2O4S/c10-9-6-8(9)7-4-2-1-3-5-7;1-5(2,3)4/h1-5,8-9H,6,10H2;(H2,1,2,3,4)/t8-,9+;/m0./s1
13492-01-8Relevant articles and documents
The synergistic effect of copper chromite spinel nanoparticles (CuCr2O4) and basic ionic liquid on the synthesis of cyclopropanecarboxylic acids
Ghasemi, Mohammad Hadi,Kowsari, Elaheh
, p. 7963 - 7975 (2016/11/25)
Abstract: An efficient synthesis of cyclopropanecarboxylic acids using copper chromite spinel nanoparticles and basic ionic liquid is described. In this study, a relatively simple method starting with trans-cinnamic acid for the synthesis of (±)-trans-2-phenylcyclopropanecarboxylic acid, a key intermediate in the synthesis of tranylcypromine sulfate as an active pharmaceutical ingredient, was employed. Using a combination of basic ionic liquid [Bmim]OH and copper chromite spinel nanoparticles as a catalytic system, the best results were obtained in THF as a polar solvent. This method is a useful alternative to other approaches described in the literature. The use of commercially available chemicals, decreased environmental hazards, with no need for the separation of stereoisomers, and consequently a reduced number of overall steps, are the advantages of this approach that make it an appropriate choice at an increased scale. Graphical Abstract: [Figure not available: see fulltext.]
