

| 
			 Pharmacokinetics  | 
			
			 Troparil is a few times more potent than cocaine as a dopamine reuptake inhibitor, but is less potent as a serotonin reuptake inhibitor, and has a duration spanning a few times longer, since the phenyl ring is directly connected to the tropane ring through a non-hydrolyzable carbon-carbon bond. The lack of an ester linkage removes the local anesthetic action from the drug, so troparil is a pure stimulant. This change in activity also makes troparil slightly less cardiotoxic than cocaine.  | 
		
InChI:InChI=1/C16H21NO2/c1-17-12-8-9-14(17)15(16(18)19-2)13(10-12)11-6-4-3-5-7-11/h3-7,12-15H,8-10H2,1-2H3/t12-,13+,14+,15-/m0/s1
Introduction Present data indicate that ...
A series of 3β-(p-substituted phenyl)tro...
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phenylmagnesium bromide


methyl ecgonidine

![(1R,3S,5S)-8-Methyl-3-phenyl-8-aza-bicyclo[3.2.1]octane-2-carboxylic acid methyl ester](/upload/2024/8/041947a4-b612-46a8-bb3e-ca6b4d95fb3a.png)
(1R,3S,5S)-8-Methyl-3-phenyl-8-aza-bicyclo[3.2.1]octane-2-carboxylic acid methyl ester
| Conditions | Yield | 
|---|---|
| 
			 phenylmagnesium bromide; methyl ecgonidine;        In   diethyl ether; dichloromethane;   at -78 - -40 ℃; for 3.5h; Inert atmosphere;  
			With    trifluoroacetic acid;     In   diethyl ether; dichloromethane;   Inert atmosphere;  
			 | 
			65.28% | 

cocaine HCl

![(1R,3S,5S)-8-Methyl-3-phenyl-8-aza-bicyclo[3.2.1]octane-2-carboxylic acid methyl ester](/upload/2024/8/041947a4-b612-46a8-bb3e-ca6b4d95fb3a.png)
(1R,3S,5S)-8-Methyl-3-phenyl-8-aza-bicyclo[3.2.1]octane-2-carboxylic acid methyl ester
| Conditions | Yield | 
|---|---|
| 
			 Multi-step reaction with 2 steps  
			1.1: hydrogenchloride / 6 h / Reflux 
			1.2: 4 h / Reflux; Inert atmosphere 
			1.3: -40 - 20 °C 
			2.1: dichloromethane; diethyl ether / 3.5 h / -78 - -40 °C / Inert atmosphere 
			2.2: Inert atmosphere 
			With    hydrogenchloride;     In   diethyl ether; dichloromethane;    
			 | 
			

phenylmagnesium bromide

methyl ecgonidine

(R)-(-)-anhydroecgonine methyl ester

methyl (1R-2-exo-3-exo)-8-methyl-3-(4-nitrophenyl)-8-azabicyclo<3.2.1>octane-2-carboxylate

methyl (1RS-2-endo-3-exo)-3-(2,4-dinitrophenyl)-8-methyl-8-azabicyclo<3.2.1>octane-2-carboxylate

methyl (1RS-2-exo-3-exo)-8-methyl-3-(4-nitrophenyl)-8-azabicyclo<3.2.1>octane-2-carboxylate

3β-(4-ethoxycarboxamidophenyl)tropane-2β-carboxylic acid methyl ester