Warning
This is an unofficial archive of PsychonautWiki as of 2025-08-08T03:33:20Z. Content on this page may be outdated, incomplete, or inaccurate. Please refer to the original page for the most up-to-date information.

Substituted tropanes: Difference between revisions

From PsychonautWiki Archive
Jump to navigation Jump to search
← Older edit
>David Hedlund
>David Hedlund
{{#set:Featured=true}}
 
(38 intermediate revisions by 4 users not shown)
Line 1: Line 1:
[[File:tropane.png|thumb|200px|right|General tropane molecule]]
[[File:tropane.png|thumb|200px|right|General tropane molecule]]
{{Stub}}
{{Stub}}
'''Tropane alkaloids''' are a class of chemicals that include compounds with [[subjective effects index|psychoactive effects]].
'''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==
==Chemistry==
Tropane alkaloids 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 R<sub>1</sub> and R<sub>5</sub> along with an additional methyl substitution at R<sub>N</sub>. Tropane alkaloids are commonly substituted at R<sub>3</sub> with an ether bridge (as seen in [[scopolamine]], [[atropine]], [[hyoscyamine]], and [[cocaine]]).
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 R<sub>1</sub> and R<sub>5</sub> along with an additional methyl substitution at R<sub>N</sub>. It is mainly known for a group of [[alkaloids]] derived from it. Tropane alkaloids are commonly substituted at R<sub>3</sub> 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==
==Pharmacology==
Line 10: Line 10:
Tropane alkaloids are mostly [[Acetylcholine#The cholinergic system|anti-cholinergics]] (antagonistic action on acetylcholine [[receptors]]) or [[stimulant]]s (prevention of [[dopamine]] reuptake).
Tropane alkaloids are mostly [[Acetylcholine#The cholinergic system|anti-cholinergics]] (antagonistic action on acetylcholine [[receptors]]) or [[stimulant]]s (prevention of [[dopamine]] reuptake).


==Examples==
==List of substituted tropanes==
Tropane alkaloids are seen throughout organic chemistry and include psychoactive and anaesthetic compounds.
{| class="wikitable"
 
|-
'''Anticholinergic drugs:'''
! scope="col" | '''Compound'''
*[[Atropine]]
! scope="col" style="width: 50px;" | '''R<sub>2</sub>'''
*[[Hyoscyamine]]
! scope="col" style="width: 50px;" | '''R<sub>3</sub>'''
*[[Scopolamine]]
! scope="col" style="width: 50px;" | '''R<sub>6</sub>'''
 
! scope="col" style="width: 50px;" | '''R<sub>7</sub>'''
'''Stimulant drugs:'''
! scope="col" | '''Structure'''
*[[Cocaine]]
|-
*[[RTI-111]]
| [[Atropine]] || H ||  OCOCH(CH<sub>2</sub>OH)C<sub>6</sub>H<sub>5</sub> || H || H || [[File:Atropine.svg|170px]]
 
|-
==See also==
| [[Hyoscyamine]] || H ||  OCOCH(CH<sub>2</sub>OH)C<sub>6</sub>H<sub>5</sub> || H || H || [[File:Hyoscyamine.svg|170px]]
*[[Responsible use]]
|-
*[[Deliriants]]
| [[Scopolamine]] || H ||  OCOCH(CH<sub>2</sub>OH)C<sub>6</sub>H<sub>5</sub> || O- || - || [[File:Scopolamine.svg|170px]]
*[[Anti-histamines]]
|-
*[[Stimulants]]
| [[Cocaine]] || CO</sub>2</sub>CH</sub>3</sub> ||  OCOC<sub>6</sub>H<sub>5</sub> || H || H || [[File:Cocaine.svg|170px]]
*[[Datura]]
|-
| [[Troparil]] || CO</sub>2</sub>CH</sub>3</sub> ||  C<sub>6</sub>H<sub>5</sub> || H || H || [[File:Troparil.svg|170px]]
|-
| [[RTI-111]] || CO</sub>2</sub>CH</sub>3</sub> ||  C<sub>6</sub>H<sub>3</sub>Cl<sub>2</sub> || H || H || [[File:RTI-111.svg|170px]]
|-
|}


==External links==
==External links==
*[https://en.wikipedia.org/wiki/Tropane Tropane (Wikipedia)]
*[[wikipedia:Tropane alkaloid|Tropane alkaloid (Wikipedia)]]
*[[wikipedia:Tropane alkaloid|Tropane alkaloid (Wikipedia)]]


==References==
==References==
{{references}}
{{references}}
[[Category:Chemical class]]
[[Category:Tropane|*]]


[[Category:Natural sources]]
{{#set:Featured=true}}

Latest revision as of 23:09, 21 April 2024

General tropane molecule

This article is a stub.

As such, it may contain incomplete or wrong information. You can help by expanding it.

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 RN. 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

This pharmacology section is incomplete.

You can help by adding to it.

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 Structure
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

References

This article does not cite enough references.

You can help by adding some.


Retrieved from "https://psy.st/index.php?title=Substituted_tropanes&oldid=482006"