Substituted tropanes

General tropane molecule

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Substituted tropanes (or simply tropanes) are a group of psychoactive compounds that include a tropane ring in their structure. Prominent examples include certain stimulants like cocaine and its derivatives as well as deliriants like atropine and scopolamine.

Chemistry

Tropanes are molecules which contain a substituted tropane ring in their structure. Tropane is a nitrogen-containing bicyclic organic molecule which consists of a piperidine and pyrrolidine ring fused at carbons R₁ and R₅ along with an additional methyl substitution at R_N. It is mainly known for a group of alkaloids derived from it. Tropane alkaloids are commonly substituted at R₃ with an ether bridge (as seen in scopolamine, atropine, hyoscyamine, and cocaine). Synthetic analogs of tropane alkaloids also exist, such as the phenyltropanes. They are not considered to be alkaloids per definition.

Pharmacology

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Tropane alkaloids are mostly anti-cholinergics (antagonistic action on acetylcholine receptors) or stimulants (prevention of dopamine reuptake).

List of substituted tropanes

Compound	R₂	R₃	R₆	R₇
Atropine	H	OCOCH(CH₂OH)C₆H₅	H	H
Hyoscyamine	H	OCOCH(CH₂OH)C₆H₅	H	H
Scopolamine	H	OCOCH(CH₂OH)C₆H₅	O-	-
Cocaine	CO2CH3	OCOC₆H₅	H	H
Troparil	CO2CH3	C₆H₅	H	H
RTI-111	CO2CH3	C₆H₃Cl₂	H	H