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Harmala alkaloid: Difference between revisions
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'''Harmaline''' is a reversible inhibitor of MAO-A (RIMA) at doses of 100mg. | '''Harmaline''' is a reversible inhibitor of MAO-A (RIMA) at doses of 100mg. | ||
====Tetrahydroharmine==== | ====Tetrahydroharmine (THH)==== | ||
[[Image:Tetrahydroharmine.svg|288px]] | [[Image:Tetrahydroharmine.svg|288px]] | ||
'''Tetrahydroharmine''' does not inhibit monoamine oxidase A. Instead, it weakly [[Reuptake inhibitor|inhibits reuptake]] of [[serotonin]]. At doses of 200mg, it has been reported to cause dream-like euphoria, pleasurable tingling sensations and an extensive array of [[psychedelic]] effects. | '''L-Tetrahydroharmine''' does not inhibit monoamine oxidase A. Instead, it weakly [[Reuptake inhibitor|inhibits reuptake]] of [[serotonin]]. At doses of 200mg, it has been reported to cause dream-like euphoria, pleasurable tingling sensations and an extensive array of [[psychedelic]] effects. | ||
'''D-THH''', on the other hand, has similar potency in terms of inhibiting MAO as harmine. | |||
==Subjective effects== | ==Subjective effects== | ||
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{{#ask: [[Category:Syrian rue]][[Category:Experience]]|format=ul|Columns=1}} | {{#ask: [[Category:Syrian rue]][[Category:Experience]]|format=ul|Columns=1}} | ||
Additional experience reports can be found here: | Additional experience reports can be found here: | ||
* [https://erowid.org/experiences/subs/exp_Harmala_Alkaloids.shtml Erowid Experience Vaults: Harmala alkaloids] | |||
*[https://erowid.org/experiences/subs/exp_Harmala_Alkaloids.shtml Erowid Experience Vaults: Harmala alkaloids] | |||
==Natural sources== | ==Natural sources== | ||
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[[File:Caapi.jpg|200px|thumb|right|''Banisteriopsis caapi'']] | [[File:Caapi.jpg|200px|thumb|right|''Banisteriopsis caapi'']] | ||
Banisteriopsis caapi (also known as ayahuasca, caapi or yajé) is a South American jungle vine of the family Malpighiaceae. It contains harmine, harmaline, and tetrahydroharmine in the following proportions: | Banisteriopsis caapi (also known as ayahuasca, caapi or yajé) is a South American jungle vine of the family Malpighiaceae. It contains harmine, harmaline, and tetrahydroharmine in the following proportions: | ||
*'''Harmine:''' 0.31-8.43% | *'''Harmine:''' 0.31-8.43% | ||
*'''Harmaline:''' 0.03-0.83% | *'''Harmaline:''' 0.03-0.83% | ||
* '''Proanthocyanidins''' (less known MAOIs) | *'''Proanthocyanidins''' (less known MAOIs) | ||
** '''(−)-epicatechin''' | **'''(−)-epicatechin''' | ||
** '''(−)-procyanidins''' | **'''(−)-procyanidins''' | ||
*'''Tetrahydroharmine:''' 0.05-2.94% | *'''Tetrahydroharmine:''' 0.05-2.94% | ||
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Syrian rue seeds contain several different harmala alkaloids at slightly varying percentages. Only some are monoamine oxidase A inhibitors. In one study, total harmala alkaloids were at least 5.9% of dried weight. | Syrian rue seeds contain several different harmala alkaloids at slightly varying percentages. Only some are monoamine oxidase A inhibitors. In one study, total harmala alkaloids were at least 5.9% of dried weight. | ||
*'''Harmane:''' 0.16% | *'''Harmane:''' 0.16% | ||
*'''Harmine:''' 0.44% (The coatings of the seeds are said to contain large amounts of harmine.) | *'''Harmine:''' 0.44% (The coatings of the seeds are said to contain large amounts of harmine.) | ||
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==Legal status== | ==Legal status== | ||
Harmala alkaloids and their natural sources are legal in most parts of the world. | Harmala alkaloids and their natural sources are legal in most parts of the world. | ||
*'''Australia:''' Harmala alkaloids are Schedule 9 drugs under [https://www.legislation.gov.au/Details/F2019L01471 ''POISONS STANDARD of DECEMBER 2019'']. HARMALA ALKALOIDS except in herbs, or preparations, for therapeutic use: | *'''Australia:''' Harmala alkaloids are Schedule 9 drugs under [https://www.legislation.gov.au/Details/F2019L01471 ''POISONS STANDARD of DECEMBER 2019'']. HARMALA ALKALOIDS except in herbs, or preparations, for therapeutic use: | ||
** containing 0.1 per cent or less of harmala alkaloids; or | **containing 0.1 per cent or less of harmala alkaloids; or | ||
** in divided preparations containing 2 mg or less of harmala alkaloids per recommended daily dose. | **in divided preparations containing 2 mg or less of harmala alkaloids per recommended daily dose. | ||
*'''Canada:''' Harmala alkaloids are Schedule III drugs. | *'''Canada:''' Harmala alkaloids are Schedule III drugs. | ||
*'''France:''' Possession and sale of harmala alkaloids is illegal. | *'''France:''' Possession and sale of harmala alkaloids is illegal. | ||
==See also== | ==See also== | ||
*[[Responsible use]] | *[[Responsible use]] | ||
*[[Beta-Carbolines]] | *[[Beta-Carbolines]] | ||
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==External links== | ==External links== | ||
* Harmala alkaloids | |||
** [http://en.wikipedia.org/wiki/Harmala_alkaloid Harmala alkaloids (Wikipedia)] | *Harmala alkaloids | ||
*** [https://en.wikipedia.org/wiki/Harmaline Harmaline (Wikipedia)] | **[http://en.wikipedia.org/wiki/Harmala_alkaloid Harmala alkaloids (Wikipedia)] | ||
*** [https://en.wikipedia.org/wiki/Harmine Harmine (Wikipedia)] | ***[https://en.wikipedia.org/wiki/Harmaline Harmaline (Wikipedia)] | ||
*** [https://en.wikipedia.org/wiki/Tetrahydroharmine Tetrahydroharmine (Wikipedia)] | ***[https://en.wikipedia.org/wiki/Harmine Harmine (Wikipedia)] | ||
** [https://erowid.org/chemicals/harmala/harmala.shtml Harmala Alkaloids (Erowid Vault)] | ***[https://en.wikipedia.org/wiki/Tetrahydroharmine Tetrahydroharmine (Wikipedia)] | ||
** [https://isomerdesign.com/PiHKAL/read.php?domain=tk&id=13 Harmaline (TiHKAL / Isomer Design)] | **[https://erowid.org/chemicals/harmala/harmala.shtml Harmala Alkaloids (Erowid Vault)] | ||
** [https://isomerdesign.com/PiHKAL/read.php?domain=tk&id=14 Harmine (TiHKAL / Isomer Design)] | **[https://isomerdesign.com/PiHKAL/read.php?domain=tk&id=13 Harmaline (TiHKAL / Isomer Design)] | ||
** [https://isomerdesign.com/PiHKAL/read.php?domain=tk&id=54 Tetrahydroharmine (TiHKAL / Isomer Design)] | **[https://isomerdesign.com/PiHKAL/read.php?domain=tk&id=14 Harmine (TiHKAL / Isomer Design)] | ||
* Natural sources | **[https://isomerdesign.com/PiHKAL/read.php?domain=tk&id=54 Tetrahydroharmine (TiHKAL / Isomer Design)] | ||
** [https://en.wikipedia.org/wiki/Banisteriopsis_caapi ''Banisteriopsis caapi'' (Wikipedia)] | *Natural sources | ||
** [https://erowid.org/plants/banisteriopsis/banisteriopsis.shtml ''Banisteriopsis caapi'' (Erowid Vault)] | **[https://en.wikipedia.org/wiki/Banisteriopsis_caapi ''Banisteriopsis caapi'' (Wikipedia)] | ||
** [https://en.wikipedia.org/wiki/Peganum_harmala ''Peganum harmala'' (Wikipedia)] | **[https://erowid.org/plants/banisteriopsis/banisteriopsis.shtml ''Banisteriopsis caapi'' (Erowid Vault)] | ||
** [https://erowid.org/plants/syrian_rue/syrian_rue.shtml Syrian rue (Erowid Vault)] | **[https://en.wikipedia.org/wiki/Peganum_harmala ''Peganum harmala'' (Wikipedia)] | ||
**[https://erowid.org/plants/syrian_rue/syrian_rue.shtml Syrian rue (Erowid Vault)] | |||
==Literature== | ==Literature== | ||
* Morales-García, J. A., de la Fuente Revenga, M., Alonso-Gil, S., Rodríguez-Franco, M. I., Feilding, A., Perez-Castillo, A., & Riba, J. (2017). The alkaloids of Banisteriopsis caapi, the plant source of the Amazonian hallucinogen Ayahuasca, stimulate adult neurogenesis in vitro. Scientific Reports, 7(1), 5309. https://doi.org/10.1038/s41598-017-05407-9 | |||
*Morales-García, J. A., de la Fuente Revenga, M., Alonso-Gil, S., Rodríguez-Franco, M. I., Feilding, A., Perez-Castillo, A., & Riba, J. (2017). The alkaloids of Banisteriopsis caapi, the plant source of the Amazonian hallucinogen Ayahuasca, stimulate adult neurogenesis in vitro. Scientific Reports, 7(1), 5309. https://doi.org/10.1038/s41598-017-05407-9 | |||
==References== | ==References== | ||
<references/> | <references /> | ||
[[Category:Substance]] | [[Category:Substance]] | ||