Harmala alkaloid: Difference between revisions

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==Chemistry==

Harmala alkaloids are substituted derivatives of the molecule [[beta-Carbolines|''beta''-carboline]]. The structure of''beta''-carboline is comprised of an indole skeleton fused to a pyridine ring. Harmine, harmaline, and ~~tetrahydroharmaline~~ share structural ~~subsitutions~~ and they all contain a methoxy group at R7 and a methyl group at R1. They differ in the saturation of their six-member nitrogenous ring. Harmine contains an unsaturated pyridine ring while harmaline contains a dihydrogenated pyridine ring. ~~Tetrahydroharmaline~~ is saturated with four additional hydrogen bonds than harmine.

Harmala alkaloids are substituted derivatives of the molecule [[beta-Carbolines|''beta''-carboline]]. The structure of''beta''-carboline is comprised of an indole skeleton fused to a pyridine ring. Harmine, harmaline, and tetrahydroharmine share structural substitutions and they all contain a methoxy group at R7 and a methyl group at R1. They differ in the saturation of their six-member nitrogenous ring. Harmine contains an unsaturated pyridine ring while harmaline contains a dihydrogenated pyridine ring. Tetrahydroharmine is saturated with four additional hydrogen bonds than harmine.

==Pharmacology==

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[[Image:Tetrahydroharmine1.png|288px]]

'''Tetrahydroharmine''' does not inhibit monoamine oxidase A. Instead, it weakly inhibits [[serotonin]] [[Reuptake inhibitor|reuptake inhibition]]. At doses of 200mg, it has been reported to cause dream-like euphoria, pleasurable tingling sensations and ~~a general~~ array of [[psychedelic]] effects.

'''Tetrahydroharmine''' does not inhibit monoamine oxidase A. Instead, it weakly inhibits [[serotonin]] [[Reuptake inhibitor|reuptake inhibition]]. At doses of 200mg, it has been reported to cause dream-like euphoria, pleasurable tingling sensations and an extensive array of [[psychedelic]] effects.

==Subjective effects==

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==Extraction==

Though ground seeds can be consumed raw, this is an unreliable method of accessing the harmala alkaloids ~~within~~. The stomach can only soak the seed material in gastric juice for a limited period before it is moved further along the digestive system for absorption of molecules in solution. Because of this, whole seeds are ineffective; ground or ~~pulverised~~ seeds work in some circumstances, but ~~in order~~ to reliably and predictably achieve psychoactivity, it is most efficient to first extract the alkaloids ~~within~~ the seeds of peganum harmala into a solution by brewing it for at least 30 minutes.

Though ground seeds can be consumed raw, this is an unreliable method of accessing the contained harmala alkaloids. The stomach can only soak the seed material in gastric juice for a limited period before it is moved further along the digestive system for absorption of molecules in solution. Because of this, whole seeds are ineffective; ground or pulverized seeds work in some circumstances, but to reliably and predictably achieve psychoactivity, it is most efficient to first extract the alkaloids from the seeds of peganum harmala into a solution by brewing it for at least 30 minutes.

The brewing environment can be enhanced by acidifying the water, using stronger solvents, and increasing the temperature. Using more water will also increase the concentration gradient, allowing more alkaloids to dissolve.

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 ==Chemistry==
-Harmala alkaloids are substituted derivatives of the molecule [[beta-Carbolines|''beta''-carboline]]. The structure of''beta''-carboline is comprised of an indole skeleton fused to a pyridine ring. Harmine, harmaline, and tetrahydroharmaline share structural subsitutions and they all contain a methoxy group at R<sub>7</sub> and a methyl group at R<sub>1</sub>. They differ in the saturation of their six-member nitrogenous ring. Harmine contains an unsaturated pyridine ring while harmaline contains a dihydrogenated pyridine ring. Tetrahydroharmaline is saturated with four additional hydrogen bonds than harmine.
+Harmala alkaloids are substituted derivatives of the molecule [[beta-Carbolines|''beta''-carboline]]. The structure of''beta''-carboline is comprised of an indole skeleton fused to a pyridine ring. Harmine, harmaline, and tetrahydroharmine share structural substitutions and they all contain a methoxy group at R<sub>7</sub> and a methyl group at R<sub>1</sub>. They differ in the saturation of their six-member nitrogenous ring. Harmine contains an unsaturated pyridine ring while harmaline contains a dihydrogenated pyridine ring. Tetrahydroharmine is saturated with four additional hydrogen bonds than harmine.
 ==Pharmacology==
@@ Line 31: / Line 31: @@
 [[Image:Tetrahydroharmine1.png|288px]]
-'''Tetrahydroharmine''' does not inhibit monoamine oxidase A. Instead, it weakly inhibits [[serotonin]] [[Reuptake inhibitor|reuptake inhibition]]. At doses of 200mg, it has been reported to cause dream-like euphoria, pleasurable tingling sensations and a general array of [[psychedelic]] effects.
+'''Tetrahydroharmine''' does not inhibit monoamine oxidase A. Instead, it weakly inhibits [[serotonin]] [[Reuptake inhibitor|reuptake inhibition]]. At doses of 200mg, it has been reported to cause dream-like euphoria, pleasurable tingling sensations and an extensive array of [[psychedelic]] effects.
 ==Subjective effects==
@@ Line 99: / Line 99: @@
 ==Extraction==
-Though ground seeds can be consumed raw, this is an unreliable method of accessing the harmala alkaloids within. The stomach can only soak the seed material in gastric juice for a limited period before it is moved further along the digestive system for absorption of molecules in solution. Because of this, whole seeds are ineffective; ground or pulverised seeds work in some circumstances, but in order to reliably and predictably achieve psychoactivity, it is most efficient to first extract the alkaloids within the seeds of peganum harmala into a solution by brewing it for at least 30 minutes.
+Though ground seeds can be consumed raw, this is an unreliable method of accessing the contained harmala alkaloids. The stomach can only soak the seed material in gastric juice for a limited period before it is moved further along the digestive system for absorption of molecules in solution. Because of this, whole seeds are ineffective; ground or pulverized seeds work in some circumstances, but to reliably and predictably achieve psychoactivity, it is most efficient to first extract the alkaloids from the seeds of peganum harmala into a solution by brewing it for at least 30 minutes.
 The brewing environment can be enhanced by acidifying the water, using stronger solvents, and increasing the temperature. Using more water will also increase the concentration gradient, allowing more alkaloids to dissolve.