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MAOI: Difference between revisions
>David Hedlund https://en.wikipedia.org/wiki/Party_pills |
>Cristobaldelicia m →Selective MAO-A inhibitors: changed "is" to "are" warning was grammatically incorrect |
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|[[Cannabis#Chemistry|Cannabis]], Cannabis extract | |[[Cannabis#Chemistry|Cannabis]], Cannabis extract | ||
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|MAO-A, MAO-B<ref name="Berlin2001"/> | |MAO-A, MAO-B<ref name="Berlin2001" /> | ||
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|[[Cocoa]] bean (from ''Theobroma cacao'') | |[[Cocoa]] bean (from ''Theobroma cacao'') | ||
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|[[Cocoa]] bean (from ''Theobroma cacao'') | |[[Cocoa]] bean (from ''Theobroma cacao'') | ||
|Catechin<ref name="Nehlig2013"/><ref name="Procyanidin flavonoids">{{cite journal | vauthors=((Gottumukkala, R. V. S. S.)), ((Nadimpalli, N.)), ((Sukala, K.)), ((Subbaraju, G. V.)) | journal=International Scholarly Research Notices | title=Determination of Catechin and Epicatechin Content in Chocolates by High-Performance Liquid Chromatography | volume=2014 | pages=628196 | date=28 October 2014 | url=https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4897191/ | issn=2356-7872 | doi=10.1155/2014/628196}}</ref> | |Catechin<ref name="Nehlig2013" /><ref name="Procyanidin flavonoids">{{cite journal | vauthors=((Gottumukkala, R. V. S. S.)), ((Nadimpalli, N.)), ((Sukala, K.)), ((Subbaraju, G. V.)) | journal=International Scholarly Research Notices | title=Determination of Catechin and Epicatechin Content in Chocolates by High-Performance Liquid Chromatography | volume=2014 | pages=628196 | date=28 October 2014 | url=https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4897191/ | issn=2356-7872 | doi=10.1155/2014/628196}}</ref> | ||
|MAO-B<ref name="Catechin, and epicatechin">{{cite journal | vauthors=((Hou, W.-C.)), ((Lin, R.-D.)), ((Chen, C.-T.)), ((Lee, M.-H.)) | journal=Journal of Ethnopharmacology | title=Monoamine oxidase B (MAO-B) inhibition by active principles from Uncaria rhynchophylla | volume=100 | issue=1–2 | pages=216–220 | date=22 August 2005 | issn=0378-8741 | doi=10.1016/j.jep.2005.03.017}}</ref> | |MAO-B<ref name="Catechin, and epicatechin">{{cite journal | vauthors=((Hou, W.-C.)), ((Lin, R.-D.)), ((Chen, C.-T.)), ((Lee, M.-H.)) | journal=Journal of Ethnopharmacology | title=Monoamine oxidase B (MAO-B) inhibition by active principles from Uncaria rhynchophylla | volume=100 | issue=1–2 | pages=216–220 | date=22 August 2005 | issn=0378-8741 | doi=10.1016/j.jep.2005.03.017}}</ref> | ||
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|[[Cocoa]] bean (from ''Theobroma cacao'') | |[[Cocoa]] bean (from ''Theobroma cacao'') | ||
|Epicatechin<ref name="Nehlig2013"/><ref name="Procyanidin flavonoids" /> | |Epicatechin<ref name="Nehlig2013" /><ref name="Procyanidin flavonoids" /> | ||
|MAO-B<ref name="Catechin, and epicatechin" /> | |MAO-B<ref name="Catechin, and epicatechin" /> | ||
|- | |- | ||
|[[Cocoa]] bean (from ''Theobroma cacao'') | |[[Cocoa]] bean (from ''Theobroma cacao'') | ||
|Tetrahydro-beta-carbolines<ref name="Nehlig2013"/> | |Tetrahydro-beta-carbolines<ref name="Nehlig2013" /> | ||
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|[[Peganum_harmala#Chemistry|Syrian rue (''Peganum harmala'')]] | |[[Peganum_harmala#Chemistry|Syrian rue (''Peganum harmala'')]] | ||
|[[Harmane]]<ref name=partial>{{cite journal |vauthors=Hemmateenejad B, Abbaspour A, Maghami H, Miri R, Panjehshahin MR |title=Partial least squares-based multivariate spectral calibration method for simultaneous determination of beta-carboline derivatives in Peganum harmala seed extracts |journal=Anal. Chim. Acta |volume=575 |issue=2 |pages=290–9 |date=August 2006 |pmid=17723604 |doi=10.1016/j.aca.2006.05.093}}</ref> | |[[Harmane]]<ref name="partial">{{cite journal |vauthors=Hemmateenejad B, Abbaspour A, Maghami H, Miri R, Panjehshahin MR |title=Partial least squares-based multivariate spectral calibration method for simultaneous determination of beta-carboline derivatives in Peganum harmala seed extracts |journal=Anal. Chim. Acta |volume=575 |issue=2 |pages=290–9 |date=August 2006 |pmid=17723604 |doi=10.1016/j.aca.2006.05.093}}</ref> | ||
|MAO-A<ref name="pmid35832393">https://www.frontiersin.org/articles/10.3389/fnmol.2022.925272/full</ref><ref name="harman">{{cite journal |last1=Herraiz |first1=T |last2=Chaparro |first2=C |title=Human monoamine oxidase enzyme inhibition by coffee and beta-carbolines norharman and harman isolated from coffee. |journal=Life sciences |date=18 January 2006 |volume=78 |issue=8 |pages=795-802 |doi=10.1016/j.lfs.2005.05.074 |pmid=16139309}}</ref><!-- Added to: MAOI, Harmala alkaloid --> | |MAO-A<ref name="pmid35832393">https://www.frontiersin.org/articles/10.3389/fnmol.2022.925272/full</ref><ref name="harman">{{cite journal |last1=Herraiz |first1=T |last2=Chaparro |first2=C |title=Human monoamine oxidase enzyme inhibition by coffee and beta-carbolines norharman and harman isolated from coffee. |journal=Life sciences |date=18 January 2006 |volume=78 |issue=8 |pages=795-802 |doi=10.1016/j.lfs.2005.05.074 |pmid=16139309}}</ref><!-- Added to: MAOI, Harmala alkaloid --> | ||
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|[[Nicotiana (botany)|Tobacco]] | |[[Nicotiana (botany)|Tobacco]] | ||
|1,2,3,4-tetrahydro-b-carboline (THbC)<ref name="Berlin2001"/> | |1,2,3,4-tetrahydro-b-carboline (THbC)<ref name="Berlin2001" /> | ||
|MAO-A, MAO-B | |MAO-A, MAO-B | ||
|- | |- | ||
|[[Nicotiana (botany)|Tobacco]] | |[[Nicotiana (botany)|Tobacco]] | ||
|1,2,3,4-tetrahydroisoquinoline<ref name="Berlin2001"/> | |1,2,3,4-tetrahydroisoquinoline<ref name="Berlin2001" /> | ||
|MAO-A, MAO-B | |MAO-A, MAO-B | ||
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*Naturally occurring sources | *Naturally occurring sources | ||
**Betel nut (''Areca catechu''): MAO-A inhibitor.<ref>{{cite journal | vauthors=((Dar, A.)), ((Khatoon, S.)), ((Rahman, G.)), ((Atta-Ur-Rahman, null)) | journal=Phytomedicine: International Journal of Phytotherapy and Phytopharmacology | title=Anti-depressant activities of Areca catechu fruit extract | volume=4 | issue=1 | pages=41–45 | date= March 1997 | issn=0944-7113 | doi=10.1016/S0944-7113(97)80026-8}}</ref><ref name="Berlin2001"/> | **Betel nut (''Areca catechu''): MAO-A inhibitor.<ref>{{cite journal | vauthors=((Dar, A.)), ((Khatoon, S.)), ((Rahman, G.)), ((Atta-Ur-Rahman, null)) | journal=Phytomedicine: International Journal of Phytotherapy and Phytopharmacology | title=Anti-depressant activities of Areca catechu fruit extract | volume=4 | issue=1 | pages=41–45 | date= March 1997 | issn=0944-7113 | doi=10.1016/S0944-7113(97)80026-8}}</ref><ref name="Berlin2001" /> | ||
**Yohimbe (''Pausinystalia johimbe''): [[Yohimbine]]<ref>{{cite journal | vauthors=((Wagmann, L.)), ((Brandt, S. D.)), ((Kavanagh, P. V.)), ((Maurer, H. H.)), ((Meyer, M. R.)) | journal=Toxicology Letters | title=In vitro monoamine oxidase inhibition potential of alpha-methyltryptamine analog new psychoactive substances for assessing possible toxic risks | volume=272 | pages=84–93 | date=15 April 2017 | issn=1879-3169 | doi=10.1016/j.toxlet.2017.03.007}}</ref> | **Yohimbe (''Pausinystalia johimbe''): [[Yohimbine]]<ref>{{cite journal | vauthors=((Wagmann, L.)), ((Brandt, S. D.)), ((Kavanagh, P. V.)), ((Maurer, H. H.)), ((Meyer, M. R.)) | journal=Toxicology Letters | title=In vitro monoamine oxidase inhibition potential of alpha-methyltryptamine analog new psychoactive substances for assessing possible toxic risks | volume=272 | pages=84–93 | date=15 April 2017 | issn=1879-3169 | doi=10.1016/j.toxlet.2017.03.007}}</ref> | ||
*Psychedelics | *Psychedelics | ||
**[[2C-T-2]] (suspected, weak)<ref name="2C-T-2 and 2C-T-7">http://www.bluelight.org/vb/threads/385484-2C-T-family-and-MAOI-properties</ref> | **[[2C-T-2]] (suspected, weak)<ref name="2C-T-2 and 2C-T-7">http://www.bluelight.org/vb/threads/385484-2C-T-family-and-MAOI-properties</ref> | ||
*** Substituted phenethylamines | ***Substituted phenethylamines are dangerous to combine with MAOIs. | ||
**[[2C-T-7]] (suspected, strong)<ref name="2C-T-2 and 2C-T-7" /> | **[[2C-T-7]] (suspected, strong)<ref name="2C-T-2 and 2C-T-7" /> | ||
*** Substituted phenethylamines | ***Substituted phenethylamines are dangerous to combine with MAOIs. | ||
**[[Bromo-DragonFLY]] (suspected, very strong)<ref>{{cite journal | vauthors=((Noble, C.)), ((Holm, N. B.)), ((Mardal, M.)), ((Linnet, K.)) | journal=Toxicology Letters | title=Bromo-dragonfly, a psychoactive benzodifuran, is resistant to hepatic metabolism and potently inhibits monoamine oxidase A | volume=295 | pages=397–407 | date=1 October 2018 | issn=1879-3169 | doi=10.1016/j.toxlet.2018.07.018}}</ref> | **[[Bromo-DragonFLY]] (suspected, very strong)<ref>{{cite journal | vauthors=((Noble, C.)), ((Holm, N. B.)), ((Mardal, M.)), ((Linnet, K.)) | journal=Toxicology Letters | title=Bromo-dragonfly, a psychoactive benzodifuran, is resistant to hepatic metabolism and potently inhibits monoamine oxidase A | volume=295 | pages=397–407 | date=1 October 2018 | issn=1879-3169 | doi=10.1016/j.toxlet.2018.07.018}}</ref> | ||
*** Dangerous to combine with MAOIs. | ***Dangerous to combine with MAOIs. | ||
*Pharmaceuticals | *Pharmaceuticals | ||
**Bifemelane (Alnert, Celeport) (available in Japan) | **Bifemelane (Alnert, Celeport) (available in Japan) | ||
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===Selective MAO-B inhibitors=== | ===Selective MAO-B inhibitors=== | ||
*Naturally occurring sources | *Naturally occurring sources | ||
**Kava (''Piper methysticum''): Yangonin. Kava pyrones: The order of potency was desmethoxyyangonin > (+/-)-methysticin > yangonin > (+/-)-dihydromethysticin > (+/-)- dihydrokavain > (+/-)-kavain.<ref>{{cite journal | vauthors=((Uebelhack, R.)), ((Franke, L.)), ((Schewe, H. J.)) | journal=Pharmacopsychiatry | title=Inhibition of platelet MAO-B by kava pyrone-enriched extract from Piper methysticum Forster (kava-kava) | volume=31 | issue=5 | pages=187–192 | date= September 1998 | issn=0176-3679 | doi=10.1055/s-2007-979325}}</ref> | **Kava (''Piper methysticum''): Yangonin. Kava pyrones: The order of potency was desmethoxyyangonin > (+/-)-methysticin > yangonin > (+/-)-dihydromethysticin > (+/-)- dihydrokavain > (+/-)-kavain.<ref>{{cite journal | vauthors=((Uebelhack, R.)), ((Franke, L.)), ((Schewe, H. J.)) | journal=Pharmacopsychiatry | title=Inhibition of platelet MAO-B by kava pyrone-enriched extract from Piper methysticum Forster (kava-kava) | volume=31 | issue=5 | pages=187–192 | date= September 1998 | issn=0176-3679 | doi=10.1055/s-2007-979325}}</ref> | ||
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====Psychoactive naturally occurring sources with high tyramine content==== | ====Psychoactive naturally occurring sources with high tyramine content==== | ||
*[[Psychedelic cacti]]. The cacti contain contain a bunch of phenethylamines, not just tyramine (but also 3-Methoxytyramine, methyltyramine, hordenine (aka dimethyltyramine), mescaline, etc) and should thus be avoided with MAOIs. However, tyramine has been identified in these species: | *[[Psychedelic cacti]]. The cacti contain contain a bunch of phenethylamines, not just tyramine (but also 3-Methoxytyramine, methyltyramine, hordenine (aka dimethyltyramine), mescaline, etc) and should thus be avoided with MAOIs. However, tyramine has been identified in these species: | ||
**[[Echinopsis peruviana|Peruvian torch cactus (''Echinopsis peruviana'' (syn. ''Trichocereus peruvianus''))]]<ref name="pubmed-600028">{{cite journal | vauthors=((Pardanani, J. H.)), ((McLaughlin, J. L.)), ((Kondrat, R. W.)), ((Cooks, R. G.)) | journal=Lloydia | title=Cactus alkaloids. XXXVI. Mescaline and related compounds from Trichocereus peruvianus | volume=40 | issue=6 | pages=585–590 | date= December 1977 | issn=0024-5461}}</ref> | **[[Echinopsis peruviana|Peruvian torch cactus (''Echinopsis peruviana'' (syn. ''Trichocereus peruvianus''))]]<ref name="pubmed-600028">{{cite journal | vauthors=((Pardanani, J. H.)), ((McLaughlin, J. L.)), ((Kondrat, R. W.)), ((Cooks, R. G.)) | journal=Lloydia | title=Cactus alkaloids. XXXVI. Mescaline and related compounds from Trichocereus peruvianus | volume=40 | issue=6 | pages=585–590 | date= December 1977 | issn=0024-5461}}</ref> | ||
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====By chemicals==== | ====By chemicals==== | ||
*Amino acids, and amino acid metabolism metabolic intermediates | *Amino acids, and amino acid metabolism metabolic intermediates | ||
**Monoamine precursors | **Monoamine precursors | ||
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{{#set:Featured=true}} | {{#set:Featured=true}} | ||
<references /> | |||