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 Content on this page may be outdated, incomplete, or inaccurate.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.
MAOI: Difference between revisions
>David Hedlund {{#set:Featured=true}} |
>David Hedlund See also RIMA#Naturally occurring sources |
||
| (31 intermediate revisions by 3 users not shown) | |||
| Line 20: | Line 20: | ||
===Before MAOI consumption=== | ===Before MAOI consumption=== | ||
*Substances with slow elimination | *Substances with slow elimination | ||
**[[Methamphetamine]]: Because of its slow elimination, low concentrations of Methamphetamine can be detected in urine for up to 7 days after a single oral dose of 30 mg (Valentine et al., 1995) or up to 60 h after a single 15-mg smoked or intravenous dose (Cook et al., 1993).<ref>{{cite journal | vauthors=((Li, L.)), ((Galloway, G. P.)), ((Verotta, D.)), ((Everhart, E. T.)), ((Baggott, M. J.)), ((Coyle, J. R.)), ((Lopez, J. C.)), ((Mendelson, J.)) | journal=The Journal of Pharmacology and Experimental Therapeutics | title=A Method to Quantify Illicit Intake of Drugs from Urine: Methamphetamine | volume=338 | issue=1 | pages=31–36 | date= July 2011 | url=https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3126645/ | issn=0022-3565 | doi=10.1124/jpet.111.179176}}</ref> A chronic meth user might still test positive seven to 10 days after consuming the drug. | **[[Methamphetamine]]: Because of its slow elimination, low concentrations of Methamphetamine can be detected in urine for up to 7 days after a single oral dose of 30 mg (Valentine et al., 1995) or up to 60 h after a single 15-mg smoked or intravenous dose (Cook et al., 1993).<ref>{{cite journal | vauthors=((Li, L.)), ((Galloway, G. P.)), ((Verotta, D.)), ((Everhart, E. T.)), ((Baggott, M. J.)), ((Coyle, J. R.)), ((Lopez, J. C.)), ((Mendelson, J.)) | journal=The Journal of Pharmacology and Experimental Therapeutics | title=A Method to Quantify Illicit Intake of Drugs from Urine: Methamphetamine | volume=338 | issue=1 | pages=31–36 | date= July 2011 | url=https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3126645/ | issn=0022-3565 | doi=10.1124/jpet.111.179176}}</ref> A chronic meth user might still test positive seven to 10 days after consuming the drug. | ||
| Line 32: | Line 31: | ||
==Poly drug use== | ==Poly drug use== | ||
*[[Ayahuasca]]: The [[tryptamine]] [[DMT]] will break down without MAOIs when taken orally. | *[[Ayahuasca]]: The [[tryptamine]] [[DMT]] will break down without MAOIs when taken orally. | ||
==List of MAOIs== | ==List of MAOIs== | ||
{{see also|RIMA#List of RIMAs}} | {{see also|RIMA#List of RIMAs}} | ||
[https://en.wikipedia.org/wiki/Party_pills Party pills] (sometimes called "herbal highs") often contain MAOIs. | |||
===Nonselective MAOIs/RIMAs=== | ===Nonselective MAOIs/RIMAs=== | ||
See also [[RIMA#Naturally occurring sources|naturally occurring RIMA sources]]. | |||
*Naturally occurring sources | *Naturally occurring sources | ||
| Line 73: | Line 74: | ||
|[[Cannabis#Chemistry|Cannabis]], Cannabis extract | |[[Cannabis#Chemistry|Cannabis]], Cannabis extract | ||
| | | | ||
|MAO-A, MAO-B<ref name="Berlin2001"/> | |MAO-A, MAO-B<ref name="Berlin2001" /> | ||
|- | |- | ||
|[[Cocoa]] bean (from ''Theobroma cacao'') | |[[Cocoa]] bean (from ''Theobroma cacao'') | ||
| Line 80: | Line 81: | ||
|- | |- | ||
|[[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> | ||
|- | |- | ||
|[[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" /> | ||
| | | | ||
|- | |- | ||
| Line 146: | Line 147: | ||
|Quercetin | |Quercetin | ||
|MAO-A | |MAO-A | ||
|- | |- | ||
|[[Peganum_harmala#Chemistry|Syrian rue (''Peganum harmala'')]] | |[[Peganum_harmala#Chemistry|Syrian rue (''Peganum harmala'')]] | ||
| Line 156: | Line 153: | ||
|- | |- | ||
|[[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 --> | ||
|- | |- | ||
| Line 162: | Line 159: | ||
|[[Harmine]] | |[[Harmine]] | ||
|[[RIMA]] | |[[RIMA]] | ||
|- | |||
|''Rhodiola rosea'' (rose root) | |||
| | |||
|MAO-A, MAO-B<ref>{{cite journal | vauthors=((Diermen, D. van)), ((Marston, A.)), ((Bravo, J.)), ((Reist, M.)), ((Carrupt, P.-A.)), ((Hostettmann, K.)) | journal=Journal of Ethnopharmacology | title=Monoamine oxidase inhibition by Rhodiola rosea L. roots | volume=122 | issue=2 | pages=397–401 | date=18 March 2009 | issn=1872-7573 | doi=10.1016/j.jep.2009.01.007}}</ref> | |||
|- | |- | ||
|[[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 | ||
|- | |- | ||
| Line 178: | Line 179: | ||
|Norharman<ref name="Tobacco" /> | |Norharman<ref name="Tobacco" /> | ||
|MAO-A, MAO-B<ref name="norharman" /> | |MAO-A, MAO-B<ref name="norharman" /> | ||
|- | |||
|Turmeric | |||
|Curcumin<ref>{{cite journal |last1=Khatri |first1=DK |last2=Juvekar |first2=AR |title=Kinetics of Inhibition of Monoamine Oxidase Using Curcumin and Ellagic Acid. |journal=Pharmacognosy magazine |date=May 2016 |volume=12 |issue=Suppl 2 |pages=S116-20 |doi=10.4103/0973-1296.182168 |pmid=27279695 |pmc=4883067}}</ref> | |||
|MAO-B | |||
|- | |- | ||
|} | |} | ||
| Line 202: | Line 207: | ||
*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) | ||
| Line 229: | Line 234: | ||
===Unknown selectivity=== | ===Unknown selectivity=== | ||
*Psychedelics | *Psychedelics | ||
**[[5-MeO-AET]] | **[[5-MeO-AET]] | ||
| Line 252: | Line 256: | ||
====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> | ||
| Line 356: | Line 361: | ||
====By pharmacotherapy==== | ====By pharmacotherapy==== | ||
*Antibiotics | *Antibiotics | ||
**Linezolid | **Linezolid | ||
| Line 404: | Line 408: | ||
===Essential vitamins and minerals=== | ===Essential vitamins and minerals=== | ||
*Vitamin B6: MAOIs may reduce blood levels of vitamin B6. Not studied on harmalas. But on tranylcypromine (a cyclopropane), and phenelzine (a hydrazine), two pharms with distinct chemical groups. | *Vitamin B6: MAOIs may reduce blood levels of vitamin B6. Not studied on harmalas. But on tranylcypromine (a cyclopropane), and phenelzine (a hydrazine), two pharms with distinct chemical groups. | ||
===Substances=== | ===Substances=== | ||
*[[Lysergamides]]: [[LSD]]. MAOIs seem to cause a greater reduction in the effects of LSD than SSRIs.<ref>{{Citation | title=Erowid LSD (Acid) Vault : LSD and Antidepressants, by Mike | url=https://erowid.org/chemicals/lsd/lsd_health3.shtml}}</ref> | *[[Lysergamides]]: [[LSD]]. MAOIs seem to cause a greater reduction in the effects of LSD than SSRIs.<ref>{{Citation | title=Erowid LSD (Acid) Vault : LSD and Antidepressants, by Mike | url=https://erowid.org/chemicals/lsd/lsd_health3.shtml}}</ref> | ||
===Research=== | ===Research=== | ||
*Naturally occurring sources | *Naturally occurring sources | ||
**''[[Mimosa tenuiflora (botany)|Mimosa tenuiflora]]'': As there have been no MAO inhibitors detected in M. tenuiflora, there is ongoing interest into how yurema exerts its visionary effects.<ref>{{Citation | title=Dimethyltryptamine - an overview, ScienceDirect Topics | url=https://www.sciencedirect.com/topics/neuroscience/dimethyltryptamine}}</ref> | **''[[Mimosa tenuiflora (botany)|Mimosa tenuiflora]]'': As there have been no MAO inhibitors detected in M. tenuiflora, there is ongoing interest into how yurema exerts its visionary effects.<ref>{{Citation | title=Dimethyltryptamine - an overview, ScienceDirect Topics | url=https://www.sciencedirect.com/topics/neuroscience/dimethyltryptamine}}</ref> | ||
==See also== | ==See also== | ||
*[[Responsible use]] | *[[Responsible use]] | ||
*[[RIMA]] | *[[RIMA]] | ||
| Line 424: | Line 424: | ||
==External links== | ==External links== | ||
*[https://en.wikipedia.org/wiki/Monoamine_oxidase_inhibitor Monoamine oxidase inhibitor (Wikipedia)] | *[https://en.wikipedia.org/wiki/Monoamine_oxidase_inhibitor Monoamine oxidase inhibitor (Wikipedia)] | ||
*[https://en.wikipedia.org/wiki/Monoamine_oxidase_A Monoamine oxidase A (Wikipedia)] | *[https://en.wikipedia.org/wiki/Monoamine_oxidase_A Monoamine oxidase A (Wikipedia)] | ||