Tropane

Base Information

• Chemical Name: Tropane
• CAS No.: 529-17-9
• Molecular Formula: C8H15 N
• Molecular Weight: 125.214
• Hs Code.: 2933990090
• European Community (EC) Number: 628-350-5
• DSSTox Substance ID: DTXSID50879243
• Nikkaji Number: J779.311A
• Wikipedia: Tropane
• Mol file: 529-17-9.mol

Synonyms:Tropane;529-17-9;8-Methyl-8-azabicyclo[3.2.1]octane;SCHEMBL44882;DTXSID50879243;MFCD24390172;AS-47573;FT-0632308;F14365

Chemical Property of Tropane

Chemical Property:

• Vapor Pressure: 1.82mmHg at 25°C
• Refractive Index: n20/D 1.477(lit.)
• Boiling Point: 166°Cat760mmHg
• PKA: 11.57±0.20(Predicted)
• Flash Point: 42.2°C
• PSA: 3.24000
• Density: 0.934g/cm³
• LogP: 1.57100
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 125.120449483
• Heavy Atom Count: 9
• Complexity: 99.1

Purity/Quality:

98%min ^*data from raw suppliers

Tropane 98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 10-36/37/38
• Safety Statements: 16-26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1C2CCCC1CC2
• General Description: 8-METHYL-8-AZABICYCLO[3.2.1]OCTANE (tropane) is a core structural motif in pharmacologically active compounds, particularly in studies targeting neurotransmitter transporters and opioid receptors. In the context of dopamine and serotonin transporters, tropane-based bivalent ligands demonstrated reduced potency, suggesting the absence of proximal binding sites for this scaffold. Conversely, tropane derivatives have been explored as selective delta opioid receptor antagonists, where structural modifications, such as alkylation at the 8-position, influence receptor affinity and antagonist activity. These findings highlight the versatility of the tropane scaffold in medicinal chemistry, with its role varying significantly depending on the target and structural modifications.

Technology Process of Tropane

There total 38 articles about Tropane which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

tropinone (532-24-1) → tropane (529-17-9,687966-22-9)

Guidance literature:

With hydrogenchloride; hydrogen; platinum(IV) oxide; for 35h; under 1.5 Torr;

Reference yield: 72.0%

N-<(benzoyloxy)carbonyl>nortropane (95799-01-2) → tropane (529-17-9,687966-22-9)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; for 24h; Ambient temperature;

DOI:10.1021/jo00211a006

Reference yield: 67.0%

1-<(methyl(4-cycloheptenyl)carbamoyl)oxy>-2(1H)-pyridinethione (122709-62-0) → tropane (529-17-9,687966-22-9)

Guidance literature:

With 2-methylpropan-2-thiol; acetic acid; In benzene; at 4 ℃;

DOI:10.3987/COM-88-S52

upstream raw materials:

N-methyl-N-cycloheptylamine

Tropidin

3-tropanol

carbon monoxide

Downstream raw materials:

8-benzoyl-8-azabicyclo<3.2.1>octane

8-azabicyclo[3.2.1]octane

N-Formylnortropan

tetraphenylethane-1,2-diol

Refernces

The synthesis of bivalent 2β-carbomethoxy-3β-(3,4-dichlorophenyl)-8-heterobicyclo[3.2.1]octanes as probes for proximal binding sites on the dopamine and serotonin transporters

10.1016/j.bmc.2007.11.009

The study investigates the synthesis and biological activity of bivalent 2b-carbomethoxy-3b-(3,4-dichlorophenyl)8-heterobicyclo[3.2.1]octanes as probes for proximal binding sites on the dopamine (DAT) and serotonin (SERT) transporters. The researchers designed bivalent compounds, where two tropane moieties are linked by an intervening chain, to explore the existence of adjacent tropane binding sites on these transporters and to compare the binding sites for different types of tropanes. The parent compounds, including 8-azatropane, 8-oxatropane, and 8-thiatropane, were synthesized and used as the basis for creating bivalent ligands with varying linker lengths. The study found that bivalent 8-azatropanes showed significantly reduced inhibitory potency at both DAT and SERT compared to their monovalent counterparts, suggesting that there are unlikely to be two tropane binding sites in close proximity on either transporter. Additionally, the results indicated that the binding sites for 8-azatropanes are different from those for 8-oxatropanes or 8-thiatropanes, as bivalent ligands containing these latter types of tropanes lost significant potency or were completely inactive at the transporters.

4-[(8-Alkyl-8-azabicyclo[3.2.1]octyl-3-yl)-3-arylanilino]-N,N-diethylbenz amides: High affinity, selective ligands for the delta opioid receptor illustrate factors important to antagonist activity

10.1016/S0960-894X(00)00209-2

The study focuses on the synthesis and evaluation of a series of tropane-derived compounds, specifically 4-[(8-alkyl-8-azabicyclo[3.2.1]octyl-3-yl)-3-arylanilino]-N,N-diethylbenzamides (denoted as 5a-d), which were designed to have high affinity and selectivity for the delta opioid receptor. These compounds are structurally similar to the piperidine-based compound 3 and were synthesized to test the hypothesis that limiting conformational flexibility could elicit antagonist activity in nitrogen-transposed compounds similar to 3. The chemicals used in the study include 3-tropanone, 3-methoxyaniline, butylated hydroxyanisole (BHA) ester of 4-fluorobenzoic acid, sodium methoxide, and various reagents for coupling and conversion reactions. The purpose of these chemicals was to synthesize the target compounds and assess their potential as selective ligands for the delta opioid receptor, with the aim of understanding the factors important to antagonist activity and potentially developing new opioid ligands with reduced side effects.

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