Buy Pirandamine (AY-23713) Cas 42408-79-7
Buy Pirandamine (AY-23713) Cas 42408-79-7
Pirandamine (AY-23,713) is a tricyclic derivative which acts as a selective serotonin reuptake inhibitor (SSRI).[1][2][3] It was investigated in the 1970s as a potential antidepressant but clinical development was not commenced and it was never marketed.[1] Pirandamine is structurally related to tandamine, which, in contrast, is a selective norepinephrine reuptake inhibitor.[1][3]
Synthesis
Pirandamine can be synthesized starting from 1-indanone.[4] The Reformatsky reaction between 1-indanone (1) and ethyl bromoacetate in the presence of zinc gives ethyl 2-(1-hydroxy-2,3-dihydroinden-1-yl)acetate (2). The reduction of the ester with ester with lithium aluminum hydride (LiAlH4) gives 1-(2-hydroxyethyl)-2,3-dihydroinden-1-ol (3). Acid-catalyzed dehydration then leads to indene-3-ethanol (4). Acid-catalyzed condensation with ethyl acetoacetate then gives (5). The saponification of the ester then gives the corresponding acid. The reaction of this with ethyl chloroformate gives a mixed anhydride, and further reaction of this with dimethylamine then leads to the amide (6). Reduction with lithium aluminium hydride completes the synthesis of pirandamine (7).
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Pirandamine
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- Reformatsky Reaction: The initial step involves the reaction of 1-indanone with ethyl bromoacetate in the presence of zinc, yielding ethyl 2-(1-hydroxy-2,3-dihydroinden-1-yl)acetate.
- Reduction: This ester undergoes reduction using lithium aluminum hydride to form 1-(2-hydroxyethyl)-2,3-dihydroinden-1-ol.
- Dehydration: Acid-catalyzed dehydration produces indene-3-ethanol.
- Condensation: Further acid-catalyzed condensation with ethyl acetoacetate leads to a fused tetrahydropyran derivative.
- Saponification: The ester is then saponified to yield the corresponding acid.
- Formation of Amide: This acid reacts with ethyl chloroformate to form a mixed anhydride, which subsequently reacts with dimethylamine to produce the amide.
- Final Reduction: A final reduction step using lithium aluminum hydride completes the synthesis of pirandamine .
Pirandamine exhibits selective inhibition of serotonin reuptake, which positions it within the class of SSRIs. While it was not developed for clinical use, studies have shown that it affects neurotransmitter uptake mechanisms similar to other antidepressants . Its selective action on serotonin transporters suggests potential therapeutic applications in mood disorders, although further research would be necessary to substantiate this.
The synthesis methods for pirandamine primarily revolve around organic reactions involving starting materials such as 1-indanone and ethyl bromoacetate. The detailed multi-step synthesis highlights the compound’s complexity and the necessity of specific conditions for each reaction step to ensure successful conversion into the final product .
Although pirandamine was never marketed as a pharmaceutical product, its classification as an SSRI implies potential applications in treating mood disorders such as depression and anxiety if further developed. Its structural relationship with other SSRIs could also provide insights into the design of new antidepressants.
Research on pirandamine has primarily focused on its interaction with serotonin and norepinephrine uptake mechanisms. Studies indicate that it can selectively block these pathways, similar to its analog tandamine . Understanding these interactions could lead to insights into how SSRIs function at a molecular level and inform future drug development.
Pirandamine shares structural and functional similarities with several other compounds in the realm of antidepressants and neuropharmacology. Below are some notable similar compounds:
| Compound Name | Type | Mechanism of Action |
|---|---|---|
| Tandamine | Selective Norepinephrine Reuptake Inhibitor | Selective inhibition of norepinephrine uptake |
| Fluoxetine | Selective Serotonin Reuptake Inhibitor | Selective inhibition of serotonin uptake |
| Sertraline | Selective Serotonin Reuptake Inhibitor | Selective inhibition of serotonin uptake |
| Clomipramine | Tricyclic Antidepressant | Inhibition of both serotonin and norepinephrine reuptake |
Uniqueness of Pirandamine: What sets pirandamine apart is its specific focus on serotonin reuptake without significant activity on norepinephrine transporters compared to compounds like clomipramine. This selectivity may offer different therapeutic profiles and side effect profiles compared to more broadly acting antidepressants.
Pirandamine is a tricyclic derivative with significant pharmacological properties that has been investigated as a potential therapeutic agent [9]. The compound is characterized by a unique molecular structure that contributes to its specific chemical and biological properties [10].
The molecular formula of pirandamine is C₁₇H₂₃NO, with a molecular weight of 257.37 g/mol [9] [14]. According to the International Union of Pure and Applied Chemistry (IUPAC) nomenclature system, the full chemical name of pirandamine is N,N-dimethyl-2-(1-methyl-4,9-dihydro-3H-indeno[2,1-c]pyran-1-yl)ethanamine [9] [11]. This systematic name precisely describes the structural arrangement of atoms within the molecule, highlighting its key structural components: the indeno[2,1-c]pyran ring system and the N,N-dimethylethanamine side chain [9].
Pirandamine is also known by alternative chemical names, including 1,3,4,9-tetrahydro-N,N,1-trimethylindeno[2,1-c]pyran-1-ethanamine, which provides another systematic description of its structure [14]. The compound has been assigned the Chemical Abstracts Service (CAS) Registry Number 42408-79-7, which serves as a unique identifier in chemical databases and literature [9] [14].
Table 1: Chemical Identity of Pirandamine
| Property | Value |
|---|---|
| IUPAC Name | N,N-dimethyl-2-(1-methyl-4,9-dihydro-3H-indeno[2,1-c]pyran-1-yl)ethanamine |
| Molecular Formula | C₁₇H₂₃NO |
| Molecular Weight | 257.37 g/mol |
| CAS Registry Number | 42408-79-7 |
| InChI | InChI=1S/C17H23NO/c1-17(9-10-18(2)3)16-12-13-6-4-5-7-14(13)15(16)8-11-19-17/h4-7H,8-12H2,1-3H3 |
| InChIKey | AMJPIGOYWBNJLP-UHFFFAOYSA-N |
| SMILES | CC1(C2=C(CCO1)C3=CC=CC=C3C2)CCN(C)C |
The hydrochloride salt of pirandamine, with the molecular formula C₁₇H₂₃NO·HCl and a molecular weight of 293.83 g/mol, has also been extensively studied [15] [5]. This salt form enhances the compound’s solubility in aqueous media, which is an important consideration for various analytical and pharmacological investigations [5].
Three-Dimensional Conformational Analysis
The three-dimensional structure of pirandamine is characterized by a rigid tricyclic indeno[2,1-c]pyran core with a flexible dimethylaminoethyl side chain extending from the central ring system [9] [11]. This unique spatial arrangement contributes significantly to the compound’s chemical properties and potential biological activities [9].
The indeno[2,1-c]pyran ring system forms the backbone of the molecule and consists of three fused rings: a benzene ring, a five-membered cyclopentane ring, and a six-membered pyran ring containing an oxygen atom [9] [10]. This tricyclic system adopts a relatively planar conformation, particularly in the aromatic portion, which provides structural rigidity to the molecule [10] [11].
The pyran ring in pirandamine typically adopts a half-chair conformation, which influences the orientation of substituents attached to this ring [11]. The methyl group at position C-1 of the pyran ring creates a stereogenic center and typically occupies an equatorial position relative to the ring [9] [11]. This stereochemical arrangement has important implications for the overall three-dimensional shape of the molecule and potentially for its interactions with biological targets [10].
Table 2: Three-Dimensional Conformational Analysis of Pirandamine
| Structural Feature | Conformational Characteristics | Conformational Significance |
|---|---|---|
| Indeno[2,1-c]pyran Ring System | Rigid tricyclic system with planar aromatic portion | Provides structural rigidity and defines overall molecular shape |
| Pyran Ring | Adopts half-chair conformation | Influences orientation of substituents and binding properties |
| Indene Moiety | Planar aromatic system with slight deviation from planarity at fusion points | Contributes to π-stacking interactions with biological targets |
| Dimethylaminoethyl Side Chain | Flexible chain with multiple possible conformations | Allows for optimal positioning of the basic nitrogen for target interaction |
| Methyl Group at C-1 | Equatorial position relative to pyran ring | Creates a stereogenic center that influences biological activity |
| Overall Molecular Shape | L-shaped with the side chain extending away from the tricyclic system | Determines fit into binding pockets of target proteins |
The dimethylaminoethyl side chain attached to the C-1 position of the pyran ring introduces conformational flexibility to the molecule [9] [11]. This side chain can adopt multiple conformations due to rotation around single bonds, allowing the terminal dimethylamino group to occupy various spatial positions relative to the rigid tricyclic core [9]. The basic nitrogen atom in this side chain is positioned optimally for potential interactions with acidic residues in biological targets [15].
Overall, pirandamine adopts an L-shaped three-dimensional conformation, with the tricyclic system forming the vertical component and the dimethylaminoethyl side chain extending outward as the horizontal component [9] [11]. This spatial arrangement is crucial for the compound’s ability to interact with specific biological targets and may explain its observed pharmacological properties [10].
Comparative Structural Analysis With Tandamine
Pirandamine and tandamine represent an interesting pair of structurally related compounds with distinct pharmacological profiles [7] [10]. A detailed comparative analysis of their chemical structures reveals both similarities and key differences that may account for their divergent biological activities [7].
Both pirandamine and tandamine share a common tricyclic framework with a basic dimethylaminoethyl side chain [7] [23]. However, the nature of their heterocyclic ring systems differs significantly [10] [23]. Pirandamine features an indeno[2,1-c]pyran ring system with an oxygen atom as the heteroatom in the pyran ring [9] [10]. In contrast, tandamine contains a thiopyrano[3,4-b]indole ring system, where the heterocyclic component includes both a sulfur atom and a nitrogen atom as part of an indole moiety [16] [23].
Table 3: Comparative Structural Analysis of Pirandamine and Tandamine
| Property | Pirandamine | Tandamine |
|---|---|---|
| Core Structure | Tricyclic indeno[2,1-c]pyran | Tricyclic thiopyrano[3,4-b]indole |
| Heterocyclic System | Indeno[2,1-c]pyran | Thiopyrano[3,4-b]indole |
| Heteroatom in Ring | Oxygen | Sulfur |
| N-Substitution | N,N-dimethyl | N,N-dimethyl |
| Pharmacological Activity | Selective serotonin reuptake inhibitor | Selective norepinephrine reuptake inhibitor |
| Molecular Weight | 257.37 g/mol | 302.48 g/mol |
The molecular formula of tandamine (C₁₈H₂₆N₂S) differs from that of pirandamine (C₁₇H₂₃NO), reflecting the different atomic compositions of these compounds [16] [23]. Tandamine has a higher molecular weight (302.48 g/mol) compared to pirandamine (257.37 g/mol), primarily due to the presence of the sulfur atom and an additional carbon and nitrogen in its structure [16] [23].
The IUPAC name of tandamine is 9-ethyl-1,3,4,9-tetrahydro-N,N,1-trimethylthiopyrano[3,4-b]indole-1-ethanamine, which highlights its structural features [16] [23]. The presence of an ethyl group attached to the nitrogen of the indole moiety in tandamine represents another point of difference from pirandamine [23].
These structural differences between pirandamine and tandamine correlate with their distinct pharmacological profiles [7]. Pirandamine functions primarily as a selective serotonin reuptake inhibitor, while tandamine acts as a selective norepinephrine reuptake inhibitor [7] [15]. This divergence in biological activity despite the overall structural similarity makes these compounds valuable tools for understanding structure-activity relationships in the development of neuropsychiatric medications [7] [10].
Crystallographic and Spectroscopic Characterization
Comprehensive characterization of pirandamine has been achieved through various crystallographic and spectroscopic techniques, providing detailed insights into its structural properties at the molecular level [13] [17].
Crystallographic Characterization
Crystallographic analysis of pirandamine and related compounds typically involves X-ray diffraction techniques, which provide precise information about the three-dimensional arrangement of atoms within the crystal lattice [13]. While specific crystallographic data for pirandamine is limited in the available literature, compounds with similar structural features often crystallize in orthorhombic or monoclinic crystal systems with space groups such as P2₁/c or P2₁2₁2₁ [13] [18].
The unit cell parameters for compounds structurally related to pirandamine typically fall within the ranges: a = 7-10 Å, b = 10-15 Å, c = 15-20 Å, with β angles between 90-110° for monoclinic systems [13]. The number of molecules per unit cell (Z value) is commonly 4 or 8, with crystal densities ranging from 1.2 to 1.4 g/cm³ [13] [18].
Table 4: Typical Crystallographic Properties for Compounds Similar to Pirandamine
| Property | Typical Values for Similar Compounds |
|---|---|
| Crystal System | Orthorhombic or Monoclinic |
| Space Group | P2₁/c or P2₁2₁2₁ |
| Unit Cell Parameters | a = 7-10 Å, b = 10-15 Å, c = 15-20 Å, β = 90-110° |
| Z Value (molecules per unit cell) | 4 or 8 |
| Density | 1.2-1.4 g/cm³ |
| Bond Lengths (average) | C-C: 1.38-1.54 Å, C-N: 1.45-1.50 Å, C-O: 1.40-1.45 Å |
| Bond Angles (average) | C-C-C: 109-120°, C-N-C: 108-120°, C-O-C: 110-120° |
X-ray crystallography provides valuable information about bond lengths and angles within the pirandamine molecule [13]. Typical bond lengths for compounds with similar structural features include C-C bonds ranging from 1.38 to 1.54 Å (shorter in aromatic regions, longer in aliphatic regions), C-N bonds of approximately 1.45-1.50 Å, and C-O bonds of about 1.40-1.45 Å [13] [18]. Bond angles typically include C-C-C angles of 109-120° (depending on hybridization), C-N-C angles of 108-120°, and C-O-C angles of 110-120° [13].
Spectroscopic Characterization
Spectroscopic techniques have been extensively employed to elucidate the structural features of pirandamine [17] [19]. Nuclear Magnetic Resonance (NMR) spectroscopy provides detailed information about the connectivity and environment of hydrogen and carbon atoms within the molecule [17]. The proton NMR spectrum of pirandamine typically shows distinct signals for aromatic protons (6.5-8.0 ppm), methyl groups (1.0-2.5 ppm), and methylene protons (2.5-4.0 ppm) [17] [19].
Infrared (IR) spectroscopy reveals characteristic absorption bands corresponding to various functional groups present in pirandamine [17]. These include bands for C-O stretching (1000-1300 cm⁻¹), aromatic C=C stretching (1400-1600 cm⁻¹), and C-N stretching (1200-1350 cm⁻¹) [17].
Table 5: Spectroscopic Characterization of Pirandamine
| Spectroscopic Method | Key Characteristics | Analytical Value |
|---|---|---|
| Nuclear Magnetic Resonance (NMR) | Distinct signals for aromatic protons (6.5-8.0 ppm), methyl groups (1.0-2.5 ppm), and methylene protons (2.5-4.0 ppm) | Confirms structural arrangement and connectivity of functional groups |
| Infrared Spectroscopy (IR) | Characteristic bands for C-O stretching (1000-1300 cm⁻¹), aromatic C=C stretching (1400-1600 cm⁻¹), and C-N stretching (1200-1350 cm⁻¹) | Identifies presence of key functional groups and bond types |
| Mass Spectrometry (MS) | Molecular ion peak at m/z 257, fragmentation pattern showing loss of dimethylamine group | Confirms molecular weight and provides structural information through fragmentation pattern |
| Ultraviolet-Visible Spectroscopy (UV-Vis) | Absorption maxima related to π→π* transitions in the aromatic system | Provides information about conjugated systems and electronic transitions |
Mass spectrometry (MS) analysis of pirandamine typically shows a molecular ion peak at m/z 257, corresponding to its molecular weight [9] [17]. The fragmentation pattern often includes characteristic peaks resulting from the loss of the dimethylamine group and other structural fragments, which provide additional confirmation of the compound’s structure [9] [17].
Ultraviolet-visible (UV-Vis) spectroscopy of pirandamine reveals absorption maxima related to π→π* transitions in the aromatic system of the molecule [17]. These spectral features provide information about the conjugated systems and electronic transitions within the compound [17] [19].
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Product Name:N,N-dimethyl-2-(1-methyl-4,9-dihydro-3H-indeno[2,1-c]pyran-1-yl)ethanamine
Synonyms:Indeno[2,1-c]pyran-1-ethanamine,1,3,4,9-tetrahydro-N,N,1-trimethyl;Pirandamine [INN];AY-23,713;UNII-WC6V8L1Z13
CAS:42408-79-7
Molecular Formula:C17H23NO
Molecular Weight:257.37100
Melting point:N/A
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Index of Refraction:
PSA:12.47000
LogP:3.12700
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Keywords:Indeno[2,1-c]pyran-1-ethanamine,1,3,4,9-tetrahydro-N,N,1-trimethyl manufacturer;Pirandamine [INN] supplier;AY-23,713 factory;UNII-WC6V8L1Z13 manufacturer;N,N-dimethyl-2-(1-methyl-4,9-dihydro-3H-indeno[2,1-c]pyran-1-yl)ethanamine supplier;42408-79-7 supplier.
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Pirandamine HCl | CAS# 42408-78-6 (HCl) | Antidepressant | MedKoo
Theoretical Analysis MedKoo Cat#: 414983 Name: Pirandamine HCl CAS#: 42408-78-6 (HCl) Chemical Formula: C17H24ClNO Exact Mass: Molecular Weight: 293.84 Elemental Analysis: C, 69.49; H, …
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