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MAOI: Difference between revisions

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>David Hedlund
Phenylalanine (tyrosine precursor): Use with caution.<ref>{{cite web |last1=Metcalf |first1=Eric |title=Phenylalanine: Uses and Risks |url=https://www.webmd.com/vitamins-and-supplements/phenylalanine-uses-and-risks |website=WebMD |language=en}}</ref>
>David Hedlund
 
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{{GenericPanel/warning
{{headerpanel|{{Template:Warning/MAOI}}}}
| title=Always check if your MAOIs also inhibit other substances. Most MAOIs are also [[cytochrome P450 inhibitors]] and some are also [[Talk:Acetylcholinesterase_inhibitor|acetylcholinesterase inhibitors]] (AChEIs)
| content=Substances that inhibits the cytochrome P450 system’s ability to metabolize certain drugs, leading to an overall increase in processing times.}}
{{For|reversible inhibitor of monoamine oxidase A|RIMA}}
{{For|reversible inhibitor of monoamine oxidase A|RIMA}}


'''Monoamine oxidase inhibitors''' (also known as '''MAOIs''') are a class of drugs which inhibit the activity of the monoamine oxidase enzyme family. They have a long history of use as medications prescribed for the treatment of depression and are particularly effective in treating atypical depression.<ref>Cristancho, Mario. "Atypical Depression in the 21st Century: Diagnostic and Treatment Issues". Psychiatric Times. Retrieved 23 November 2013.</ref> They are also used in the treatment of social anxiety, Parkinson's disease and several other disorders.<ref>https://nardil.org</ref>
'''Monoamine oxidase inhibitors''' (also known as '''MAOIs''') are a class of drugs which inhibit the activity of the monoamine oxidase enzyme family. They have a long history of use as medications prescribed for the treatment of depression and are particularly effective in treating atypical depression.<ref>{{cite journal | vauthors=((Mario A. Cristancho, M. D.)), ((John P. O’reardon, M. D.)), ((Michael E. Thase, M. D.)) | journal=Psychiatric Times | title=Atypical Depression in the 21st Century: Diagnostic and Treatment Issues | volume=28 | issue=1 | date=20 November 2012 | url=https://www.psychiatrictimes.com/view/atypical-depression-21st-century-diagnostic-and-treatment-issues | access-date = November 23, 2013}}</ref> They are also used in the treatment of social anxiety, Parkinson's disease and several other disorders.<ref>{{Citation | year=2020 | title=Nardil (Phenelzine Sulfate) - The BEST Antidepressant For Social Anxiety & Depression | url=https://nardil.org/}}</ref>


==Mechanism of action==
==Mechanism of action==
MAOIs act by inhibiting the activity of monoamine oxidase, preventing the breakdown of monoamine neurotransmitters and thereby increasing their availability. There are two isoforms of monoamine oxidase, MAO-A and MAO-B.  
MAOIs act by inhibiting the activity of monoamine oxidase, preventing the breakdown of monoamine neurotransmitters and thereby increasing their availability. There are two isoforms of monoamine oxidase, MAO-A and MAO-B.  


MAOA preferentially deaminates [[norepinephrine]] (NE), [[serotonin]] (5-HT) and [[epinephrine]] (E), while MAOB preferentially deaminates benzylamine and [[phenylethylamine]] (PEA). [[Dopamine]] (DA) and [[tyramine]] are equally catabolized by both forms of MAO.<ref>https://www.ncbi.nlm.nih.gov/pubmed/11343627</ref>
Monoamine oxidase A (MAOA) generally metabolizes tyramine, norepinephrine (NE), serotonin (5-HT), and dopamine (DA) (and other less clinically relevant chemicals). In contrast, monoamine oxidase B (MAOB) mainly metabolizes dopamine (DA) (and other less clinically relevant chemicals).


===Reversibility===
===Reversibility===
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==Consumption planning for MAOIs==
==Consumption planning for MAOIs==
{{mbox|type=notice|text=See the [[#Tyramine|tyramine]] section for foods with high tyramine content.}}
Not only avoid the consumption but also the handling of substances with dangerous MAOI interactions (in case they are absorbed unintentionally, e.g. via breathing, skin absorption, or contaminated fingers to mouth, nose, eyes, etc).
Not only avoid the consumption but also the handling of substances with dangerous MAOI interactions (in case they are absorbed unintentionally, e.g. via breathing, skin absorption, or contaminated fingers to mouth, nose, eyes, etc).


===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>https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3126645/</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.
*Pharmacotherapy examples
*Pharmacotherapy examples
**[[#Nonselective_MAO-A_and_MAO-B_inhibitors|Cannabinoids]]: Cannabinoids are lipophilic. For example, THC has been detected in heavy cannabis users after 77 days of drug abstinence (Ellis et al., 1985).<ref>https://www.ncbi.nlm.nih.gov/pubmed/3902318</ref>
**[[#Nonselective_MAO-A_and_MAO-B_inhibitors|Cannabinoids]]: Cannabinoids are lipophilic. For example, THC has been detected in heavy cannabis users after 77 days of drug abstinence (Ellis et al., 1985).<ref>{{cite journal | vauthors=((Ellis, G. M.)), ((Mann, M. A.)), ((Judson, B. A.)), ((Schramm, N. T.)), ((Tashchian, A.)) | journal=Clinical Pharmacology and Therapeutics | title=Excretion patterns of cannabinoid metabolites after last use in a group of chronic users | volume=38 | issue=5 | pages=572–578 | date= November 1985 | issn=0009-9236 | doi=10.1038/clpt.1985.226}}</ref>
**SSRIs: Because of the extended half-life of norfluoxetine, a '''minimum of 5 weeks''' should lapse between stopping fluoxetine (20 mg/day) and starting an MAOI. With higher doses the interval should be longer. For example, a serotonin syndrome was reported following a 6-weeks washout in a patient who had been given fluoxetine (80 mg/day).<ref>Principles and Practice of Psychopharmacotherapy, page 250</ref>
**SSRIs: Because of the extended half-life of norfluoxetine, a <span style="color:red">'''minimum of 5 weeks'''</span> should lapse between stopping fluoxetine (20 mg/day) and starting an MAOI. With higher doses the interval should be longer. For example, a serotonin syndrome was reported following a 6-weeks washout in a patient who had been given fluoxetine (80 mg/day).<ref>{{cite book | vauthors=((Janicak, P. G.)), ((Marder, S. R.)), ((Pavuluri, M. N.)) | date=26 December 2011 | title=Principles and Practice of Psychopharmacotherapy | publisher=Lippincott Williams & Wilkins | isbn=9781451178777}}</ref>
*Tolerance from heavy substance use or therapy may cause [https://en.wikipedia.org/wiki/Post-acute-withdrawal_syndrome post-acute-withdrawal syndrome] (PAWS). The condition gradually improves over a period of time which can range from six months to several years in more severe cases.<ref>{{cite journal | author=Roberts AJ |author2=Heyser CJ |author3=Cole M |author4=Griffin P |author5=Koob GF  |date=June 2000 | title=Excessive ethanol drinking following a history of dependence: animal model of allostasis | journal =Neuropsychopharmacology | volume=22 | issue=6 | pages=581–94 | pmid=10788758 | doi=10.1016/S0893-133X(99)00167-0}}</ref><ref>{{cite journal | vauthors=De Soto CB, O'Donnell WE, De Soto JL |date=October 1989 | title =Long-term recovery in alcoholics | journal =Alcohol Clin Exp Res | volume =13 | issue =5 | pages =693–7 | pmid =2688470 | doi =10.1111/j.1530-0277.1989.tb00406.x }}</ref>
*Tolerance from heavy substance use or therapy may cause [https://en.wikipedia.org/wiki/Post-acute-withdrawal_syndrome post-acute-withdrawal syndrome] (PAWS). The condition gradually improves over a period of time which can range from six months to several years in more severe cases.<ref>{{cite journal | author=Roberts AJ |author2=Heyser CJ |author3=Cole M |author4=Griffin P |author5=Koob GF  |date=June 2000 | title=Excessive ethanol drinking following a history of dependence: animal model of allostasis | journal =Neuropsychopharmacology | volume=22 | issue=6 | pages=581–94 | pmid=10788758 | doi=10.1016/S0893-133X(99)00167-0}}</ref><ref>{{cite journal | vauthors=De Soto CB, O'Donnell WE, De Soto JL |date=October 1989 | title =Long-term recovery in alcoholics | journal =Alcohol Clin Exp Res | volume =13 | issue =5 | pages =693–7 | pmid =2688470 | doi =10.1111/j.1530-0277.1989.tb00406.x }}</ref>


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==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.
==Interactions==
{{mbox|type=notice|text=This section will never be complete since too many substances interact with MAOIs. Independent research should always be done to ensure that a combination of two or more substances is safe before consumption. However, not everything is documented and animal studies is not always reliable, so always start with [https://en.wikipedia.org/wiki/Microdosing microdoses].}}
When the CYP450 system is impacted in this way, it leads to higher levels of certain drugs in your system at one time. This can cause unwanted side effects, and sometimes, an overdose.
===Tyramine===
Tyramine causes hypertensive crises after MAO inhibition aka the "cheese effect" or "cheese crisis". Using a MAO inhibitor (MAOI), the intake of approximately 10 to 25 mg of tyramine is required for a severe reaction compared to 6 to 10 mg for a mild reaction.<ref>https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2738414/</ref> Tyramine rich food should also be avoided by people prone to headache and migraine.
====Psychoactive substances====
Naturally occurring sources with tyramine.
*[[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">https://www.ncbi.nlm.nih.gov/m/pubmed/600028/</ref>
**[[Echinopsis pachanoi|San Pedro cactus (''Echinopsis pachanoi'' (syn. ''Trichocereus pachanoi''))]]<ref>{{cite journal|author1=Crosby, D.M. |author2=McLaughlin, J.L.|title=Cactus Alkaloids. XIX Crystallization of Mescaline HCl and 3-Methoxytyramine HCl from Trichocereus panchanoi| journal=Lloydia and the Journal of Natural Products| date=Dec 1973 |volume=36 |issue=4 |pages=416–418 |pmid=4773270 |url=http://catbull.com/alamut/Bibliothek/1973_d.m._crosby_8158_1.pdf |accessdate=13 December 2013}}</ref>
**Other cactis:
{| class="wikitable sortable" border="1" style="font-size:smaller"
|-
!Specie
!Tyramine (mg/gram of alive plant)<ref name="Grym">Grym, Rudolf (1997). Rod/Die Gattung Lophophora. Bratislava: Vydavateľstvo Roman Staník. ISBN 80-900933-9-6. (The book features an appendix on Lophophora chemistry by Dr Roman Štarha.)</ref>
|-
|''[[Lophophora williamsii (botany)|L. williamsii]]''
!0.5 - 1
|-
|''[[Lophophora jourdaniana (botany)|L. jourdaniana]]''
!0.6
|-
|''[[Lophophora diffusa (botany)|L. diffusa]]''
!0.1
|-
|''[[Lophophora fricii (botany)|L. fricii]]''
!0.1
|-
|''[[Lophophora koehresii (botany)|L. koehresii]]''
!0.1
|-
|}
====Food====
Specific foods with high amounts of [[tyramine]]:<ref name="Kathrynne">https://www.mc.vanderbilt.edu/documents/neurology/files/Tyramine%20Menu%20Book%2006227101.pdf</ref><ref name="Estimates of maximum tolerable levels of tyramine content in foods in Austria" /><ref>McCabe-Sellers BJ, Staggs CG, and Bogle ML. Tyramine in foods and monoamine oxidase inhibitor drugs: A crossroad where medicine, nutrition, pharmacy and food industry converge; J Food Comp Anal. 2006; 19:S58.  | http://naldc.nal.usda.gov/download/7351/PDF</ref>
*Aged cheese (gouda, camembert, cheddar) -- Few cheeses (even. 'mature' cheeses) contain more than 25 mg of tyramine in 100 grams.<ref>https://psychotropical.info/wp-content/uploads/2018/02/MAOI_diet_drug_interactions_2017.pdf</ref> However, Stilton (a blue cheese) contains up to 217 mg tyramine per 100 grams.<ref name="Kathrynne" />
*Aged, smoked or pickled meats
*Aged or fermented soy and yeast products (soy sauce, teriyaki sauce, home baked yeast bread, sourdough bread)
*Overripe fruits
*High amounts of nuts
Candy, and dried fruit:
*[[Cocoa#Chemistry|Cocoa]]
**[[Chocolate milk]]
**Chocolate, especially dark chocolate
**Dried and/or candied fruit rolled in cocoa powder
*Licorice (isoliquiritigenin and liquiritigenin are [[#Nonselective_MAO-A_and_MAO-B_inhibitors|non-selective MAOIs]]).<ref name="pubmed-11501051" />
**Licorice candy
**Dried and/or candied fruit rolled in licorice powder
Tyramine formation has been associated with bacterial contamination of foods or temperature abuse conditions, but can also occur as a side effect of generally desired ripening processes.<ref name="Estimates of maximum tolerable levels of tyramine content in foods in Austria">http://vup.sk/en/download.php?bulID=1294</ref> Tyramine is a breakdown product of the amino acid L-tyrosine.
===Psychoactive substances===
The MAOIs are well-known for their numerous drug interactions, including the following kinds of substances:
*Substances that are metabolized by monoamine oxidase, as they can be boosted by up to several-fold
*Substances that increase serotonin, noradrenaline, or dopamine activity as too much of any of these neurotransmitters can result in severe acute consequences including [[serotonin syndrome]], hypertensive crisis, and psychosis.
====By chemicals====
*[[Adrenergic]]s
*[[Lysergamides]]: [[LSA]] ([[morning glory]]: (''[[Argyreia nervosa]]'', ''[[Ipomoea tricolor]]'', etc)<ref>https://www.erowid.org/plants/morning_glory/morning_glory_basics.shtml</ref>
*[[Monoaminergic]]s (MA)
**[[Cholinergic]]s (see also MAOIs that act as [[Talk:Acetylcholinesterase_inhibitor|acetylcholinesterase inhibitor]]s (AChEIs)), certain substances, examples: [[alpha-GPC|''alpha''-GPC]] (suspected monoaminergic),<ref name="Alpha-GPC and citicoline">https://www.ncbi.nlm.nih.gov/pubmed/23244432</ref><ref>https://www.ncbi.nlm.nih.gov/pubmed/3709792</ref> [[centrophenoxine]],<ref name="Effect of centrophenoxine, piracetam and aniracetam on the monoamine oxidase activity in different brain structures of rats" /> [[citicoline]] (suspected monoaminergic)<ref name="Alpha-GPC and citicoline" /><ref>https://www.ncbi.nlm.nih.gov/pubmed/17171187</ref>
**[[#List of MAOIs|MAOI]]s, avoid mixing pure MAOIs. Plants with multiple MAOIs like ''Peganum harmala'' are fine since they have been evaluated.
***[[RIMA]]s
*Disinhibitors
**Norepinephrine and dopamine disinhibitors (NDDIs): [[Fluoxetine]]
*Neurotransmitter precursors
**Dopamine: <small>L</small>-DOPA. L-tyrosine (L-DOPA precursor): It is unknown if MAOIs interact with tyrosine, so use with caution.<ref>{{cite web |title=Tyrosine: Benefits, Side Effects and Dosage |url=https://www.healthline.com/nutrition/tyrosine |website=Healthline |language=en |date=1 February 2018}}</ref> Phenylalanine (tyrosine precursor): Use with caution.<ref>{{cite web |last1=Metcalf |first1=Eric |title=Phenylalanine: Uses and Risks |url=https://www.webmd.com/vitamins-and-supplements/phenylalanine-uses-and-risks |website=WebMD |language=en}}</ref>
**Epinephrine (adrenaline): <small>L</small>-DOPA, [[SAM-e]]
**Melatonin: L-tryptophan
**Norepinephrine (noradrenaline): <small>L</small>-DOPA
**Serotonin: [[5-HTP]], [[L-tryptophan]]
*Opioids: Some opioid analgesics are associated with a risk of serotonin syndrome in combination with MAOIs due to their serotonergic properties. Other combinations may result in opioid toxicity due to CYP450 enzyme inhibition by the MAOI. Given the widespread availability of several suitable alternative drugs, the combination of dextromethorphan, methadone, pethidine, tramadol, fentanyl or tapentadol with an MAOI should usually be avoided, including in the 14 day period following the withdrawal of an irreversible MAOI. Morphine, codeine, oxycodone and buprenorphine are alternative opioids for patients receiving MAOIs, though starting at a low dose and titrating cautiously against clinical response is advised.<ref>https://www.sps.nhs.uk/articles/what-is-the-risk-of-interaction-between-opioids-and-monoamine-oxidase-inhibitors-maois/</ref>
*[[Racetam]]s: [[Aniracetam]],<ref name="Effect of centrophenoxine, piracetam and aniracetam on the monoamine oxidase activity in different brain structures of rats">https://www.ncbi.nlm.nih.gov/pubmed/3137089</ref> [[piracetam]]<ref name="Effect of centrophenoxine, piracetam and aniracetam on the monoamine oxidase activity in different brain structures of rats" />
*Receptor agonists
**Serotonin receptor agonist
***5-HT<sub>1A</sub>: [[CBD]]<ref name="pmid16258853">{{cite journal | vauthors = Russo EB, Burnett A, Hall B, Parker KK | title = Agonistic properties of cannabidiol at 5-HT1a receptors | journal = Neurochemical Research | volume = 30 | issue = 8 | pages = 1037–43 | date = August 2005 | pmid = 16258853 | doi = 10.1007/s11064-005-6978-1 }}</ref>
**Dopamine receptor agonist, examples: amphetamines ([[amphetamine]], [[lisdexamfetamine]], [[methamphetamine]]), [[cathinone]], [[cocaine]], [[PCP]], [[phenethylamine]], [[salvinorin A]] (found in ''[[Salvia divinorum]]''),<ref>Seeman P, Guan HC, Hirbec H (2009). "Dopamine D2High receptors stimulated by phencyclidines, lysergic acid diethylamide, salvinorin A, and modafinil". Synapse 63 (8): 698–704. doi:10.1002/syn.20647. PMID: 19391150</ref> [[tyramine]]
***D2: [[CBD]],<ref>https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5315552/</ref>
*[[Releasing agent]]s and monoamine releasing agent (MRA) (or monoamine releaser)
**Dopamine releasing agent (DRA)
**Norepinephrine releasing agent (NRA) (or adrenergic releasing agent), examples: [[Adrenaline]], [[ephedrine]], [[pseudoephedrine]]
**Norepinephrine-dopamine releasing agents (NDRAs), examples: [[Amphetamine]], [[cathinone]], [[phenethylamine]], [[tyramine]], [[methamphetamine]]
**Serotonin releasing agent (SRA)
***[[Dextropropoxyphene]]
***[[Diphenhydramine]]
***[[DXM]]
***Selective serotonin releasing agent (SSRA), examples: [[MDAI]], [[PMA]], [[PMMA]]
**Serotonin–norepinephrine-dopamine releasing agent (SNDRA) (also known as a triple releasing agent (TRA)), examples:
***Amphetamines: [[MDA]], [[MDMA]], [[methamphetamine]]
***Substituted benzofurans: [[5-APB]], [[6-APB]]
***Substituted cathinones: [[mephedrone]]
***Tryptamines: [[αET]], [[αMT]]
*[[Reuptake inhibitor]]s and monoamine reuptake inhibitors (MRIs)
**Dopamine reuptake inhibitors (DRI), examples: [[Armodafinil]], [[ethylphenidate]], [[methylphenidate]], [[modafinil]]
**Norepinephrine reuptake inhibitor (NRI, NERI) (or adrenergic reuptake inhibitor (ARI)), example: [[Tapentadol]]
**Norepinephrine-dopamine reuptake inhibitors (NDRI), examples: [[Ethylphenidate]], [[methylphenidate]], [[prolintane]]. Suspected: [[A-PVP]], [[desoxypipradrol]], [[MDPV]]
**Serotonin reuptake inhibitor (SRA)
***[[Selective serotonin reuptake inhibitor]]s (SSRI), examples: [[Selective_serotonin_reuptake_inhibitor#Citalopram|Citalopram]], [[Selective_serotonin_reuptake_inhibitor#escitalopram|escitalopram]], [[Selective_serotonin_reuptake_inhibitor#Fluoxetine|fluoxetine]], [[Selective_serotonin_reuptake_inhibitor#Fluvoxamine|fluvoxamine]], [[Selective_serotonin_reuptake_inhibitor#Paroxetine|paroxetine]], [[Selective_serotonin_reuptake_inhibitor#Sertraline|sertraline]]
**Serotonin–norepinephrine–dopamine reuptake inhibitor (SNDRI), also known as a triple reuptake inhibitor (TRI), examples:
***[[6-APB]]
***[[Cocaine]]
***[[Ketamine]]
***[[PCP]]
***St. Johnswort (''Hypericum perforatum'')
*Serotonin modulator and stimulator (SMS)
*[[Substituted cathinone]]s, examples: [[a-PVP]], [[MDPV]], [[methylone]], [[mephedrone]]
*[[Substituted phenethylamines]]
**[[Amphetamines]], examples: [[Amphetamine]], [[dextroamphetamine]], [[methamphetamine]]
**Psychedelic phenethylamines, examples: [[2C-x]] (and NBs for example [[25x-NBOH]], [[25x-NBOMe]]), [[DOx]], [[MDMA]], [[mescaline]] ([[psychedelic cacti]])
*[[Tryptamine#List_of_substituted_tryptamines|Substituted tryptamines]], examples:
**5-MeO-''xx''T: [[5-MeO-AMT]],<ref>https://erowid.org/chemicals/5meo_amt/5meo_amt_basics.shtml</ref> [[5-MeO-DiPT]],<ref name="The effects of non-medically used psychoactive drugs on monoamine neurotransmission in rat brain">https://www.ncbi.nlm.nih.gov/pubmed/17223101</ref> [[5-MeO-DMT]],<ref name="The effects of non-medically used psychoactive drugs on monoamine neurotransmission in rat brain" /><ref>https://erowid.org/chemicals/5meo_dmt/5meo_dmt_health.shtml</ref> [[5-MeO-MiPT]]<ref name="The effects of non-medically used psychoactive drugs on monoamine neurotransmission in rat brain" /><ref>https://erowid.org/chemicals/5meo_mipt/5meo_mipt_basics.shtml</ref>
*Tetracyclic antidepressants (TeCA), example: [[Mirtazapine]]
*Tricyclic antidepressants (TCA), example: [[Tianeptine]]
*[[Tropane alkaloids]]
**Anticholinergics (found in (''[[Datura]] spp.'', ''[[Hyoscyamus niger (botany)|Hyoscyamus niger]]'', etc)<ref>https://www.erowid.org/plants/datura/datura_faq.shtml</ref>)
***[[Atropine]]
***[[Hyoscyamine]]
***[[Scopolamine]]
**Stimulants
***[[Cocaine]]
***[[RTI-111]]
*[[Xanthine]]s: Caffeine<ref>https://www.jwatch.org/fw108796/2014/05/06/severe-hypertension-linked-caffeine-mao-inhibitor</ref>
====By pharmacotherapy====
*Antibiotics
**Linezolid
*Anticholinergics
**Hyoscine, also known as scopolamine: The transdermal patch (''e.g.,'' Transderm Scōp) for prevention of nausea and motion sickness employs hyoscine base, and is effective for up to three days.<ref>{{cite web |url = http://www.transdermscop.com/prescribing-information.htm |title = Transderm Scop patch prescribing information |archive-url = https://web.archive.org/web/20090204034217/http://www.transdermscop.com/prescribing-information.htm |archive-date = 4 February 2009 |df = dmy-all }}</ref>
*Antihistamines (allergy medicines), example but not limited to:
**Desloratadine -- hay fever medicine.
**Loratadine -- hay fever medicine.
*Antitussives
**Cold medicine
*Decongestants
**[[Naphazoline]]
*Essential nutrients
**Choline
***Certain cholinergics (see "Cholinergics")
*Local and general anesthetic
*Vasoconstrictors
**[[Naphazoline]] (brand name Clear Eyes, Cleari -- Eye drops used to treat red eyes, caused by for example [[cannabis]] that induces corneal vasodilation)
====Over-the-counter (OTC) medicines====
===Dangerous interactions===
{{DangerousInteractions/Intro}}
{{DangerousInteractions/MAOIs}}
==Reduced bio-availability==
===Essential vitamins and minerals===
*Vitamin B6: MAOIs may reduce blood levels of vitamin B6.
===Substances===
*[[Lysergamides]]: [[LSD]]. MAOIs seem to cause a greater reduction in the effects of LSD than SSRIs.<ref>https://erowid.org/chemicals/lsd/lsd_health3.shtml</ref>


==List of MAOIs==
==List of MAOIs==
{{see also|RIMA#List of RIMAs}}
{{see also|RIMA#List of RIMAs}}


===Nonselective MAO-A and MAO-B inhibitors===
[https://en.wikipedia.org/wiki/Party_pills Party pills] (sometimes called "herbal highs") often contain MAOIs.
 
===Nonselective MAOIs/RIMAs===
See also [[RIMA#Naturally occurring sources|naturally occurring RIMA sources]].


*Naturally occurring sources
*Naturally occurring sources
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!Natural occuring source
!Natural occuring source
!Chemical
!Chemical
!MAOI type
|-
|-
|''[[Banisteriopsis caapi#Chemistry|Banisteriopsis caapi]]'' (ayahuasca, caapi or yagé)
|''[[Banisteriopsis caapi#Chemistry|Banisteriopsis caapi]]'' (ayahuasca, caapi or yagé)
Line 227: Line 61:
|-
|-
|''[[Banisteriopsis caapi#Chemistry|Banisteriopsis caapi]]'' (ayahuasca, caapi or yagé)
|''[[Banisteriopsis caapi#Chemistry|Banisteriopsis caapi]]'' (ayahuasca, caapi or yagé)
|[[Harmine]]<ref name="sciencedirect.com/topics/neuroscience/banisteriopsis-caapi">https://www.sciencedirect.com/topics/neuroscience/banisteriopsis-caapi</ref>
|[[Harmine]]<ref name="sciencedirect.com/topics/neuroscience/banisteriopsis-caapi">{{Citation | title=Banisteriopsis Caapi - an overview, ScienceDirect Topics | url=https://www.sciencedirect.com/topics/neuroscience/banisteriopsis-caapi}}</ref>
|MAO-A, MAO-B
|[[RIMA]]
|-
|''Camellia sinensis'' (tea plant)
|[[Harmane]]<ref>{{Cite journal|last=Jiao|first=Ye|last2=Yan|first2=Yan|last3=He|first3=Zhiyong|last4=Gao|first4=Daming|last5=Qin|first5=Fang|last6=Lu|first6=Mei|last7=Xie|first7=Mingyong|last8=Chen|first8=Jie|last9=Zeng|first9=Maomao|date=2018-06-20|title=Inhibitory effects of catechins on β-carbolines in tea leaves and chemical model systems|url=https://pubmed.ncbi.nlm.nih.gov/29789822|journal=Food & Function|volume=9|issue=6|pages=3126–3133|doi=10.1039/c7fo02053h|issn=2042-650X|pmid=29789822}}</ref>
|MAO-A<ref name="pmid35832393" /><ref name="harman" />
|-
|-
|[[Piper nigrum (botany)|Black pepper]] (''Piper nigrum'')
|[[Piper nigrum (botany)|Black pepper]] (''Piper nigrum'')
|Piperine<ref name="pubmed-15120460">https://www.ncbi.nlm.nih.gov/pubmed/15120460</ref>
|Piperine<ref name="pubmed-15120460">{{cite journal | vauthors=((Kong, L. D.)), ((Cheng, C. H. K.)), ((Tan, R. X.)) | journal=Journal of Ethnopharmacology | title=Inhibition of MAO A and B by some plant-derived alkaloids, phenols and anthraquinones | volume=91 | issue=2–3 | pages=351–355 | date= April 2004 | issn=0378-8741 | doi=10.1016/j.jep.2004.01.013}}</ref>
|MAO-A, MAO-B
|MAO-A, MAO-B
|-
|-
|[[Cannabis#Chemistry|Cannabis]], Cannabis extract
|[[Cannabis#Chemistry|Cannabis]], Cannabis extract
|
|
|MAO-A, MAO-B<ref name="Monoamine oxidases and tobacco smoking." />
|MAO-A, MAO-B<ref name="Berlin2001" />
|-
|-
|[[Cocoa]] bean (from ''Theobroma cacao'')
|[[Cocoa]] bean (from ''Theobroma cacao'')
|[[Caffeine]]<ref name="Cacao content">https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3575938/</ref>
|[[Caffeine]]<ref name="Nehlig2013">{{cite journal | vauthors=((Nehlig, A.)) | journal=British Journal of Clinical Pharmacology | title=The neuroprotective effects of cocoa flavanol and its influence on cognitive performance | volume=75 | issue=3 | pages=716–727 | date= March 2013 | url=https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3575938/ | issn=0306-5251 | doi=10.1111/j.1365-2125.2012.04378.x}}</ref>
|MAO-A, MAO-B<ref name="Caffeine" />
|MAO-A, MAO-B<ref name="Caffeine" />
|-
|-
|[[Cocoa]] bean (from ''Theobroma cacao'')
|[[Cocoa]] bean (from ''Theobroma cacao'')
|Catechin<ref>https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3575938/</ref><ref name="Procyanidin flavonoids">https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4897191/</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">https://www.ncbi.nlm.nih.gov/pubmed/15890481</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>https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3575938/</ref><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>https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3575938/</ref>
|Tetrahydro-beta-carbolines<ref name="Nehlig2013" />
|
|
|-
|-
|[[Coffea (botany)|Coffee]] (''Coffea arabica'', ''Coffea canephora'')
|[[Coffea (botany)|Coffee]] (''Coffea arabica'', ''Coffea canephora'')
|[[Caffeine]]
|[[Caffeine]]
|MAO-A, MAO-B<ref name="Caffeine">https://www.ncbi.nlm.nih.gov/pubmed/23850513</ref>
|MAO-A, MAO-B<ref name="Caffeine">{{cite journal | vauthors=((Petzer, A.)), ((Pienaar, A.)), ((Petzer, J. P.)) | journal=Life Sciences | title=The interactions of caffeine with monoamine oxidase | volume=93 | issue=7 | pages=283–287 | date=28 August 2013 | issn=1879-0631 | doi=10.1016/j.lfs.2013.06.020}}</ref>
|-
|-
|[[Coffea (botany)|Coffee]] (''Coffea arabica'', ''Coffea canephora'')
|[[Coffea (botany)|Coffee]] (''Coffea arabica'', ''Coffea canephora'')
|Harman<ref name="Coffea">https://www.ncbi.nlm.nih.gov/pubmed/16139309</ref>
|[[Harmane]]<ref name="Coffea">{{cite journal | vauthors=((Herraiz, T.)), ((Chaparro, C.)) | journal=Life Sciences | title=Human monoamine oxidase enzyme inhibition by coffee and beta-carbolines norharman and harman isolated from coffee | volume=78 | issue=8 | pages=795–802 | date=18 January 2006 | issn=0024-3205 | doi=10.1016/j.lfs.2005.05.074}}</ref>
|MAO-A, MAO-B<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>
|MAO-A<ref name="pmid35832393" /><ref name="harman" />
|-
|-
|[[Coffea (botany)|Coffee]] (''Coffea arabica'', ''Coffea canephora'')
|[[Coffea (botany)|Coffee]] (''Coffea arabica'', ''Coffea canephora'')
Line 271: Line 109:
|-
|-
|Liquorice/licorice (''Glycyrrhiza Glabra'')
|Liquorice/licorice (''Glycyrrhiza Glabra'')
|Liquiritigenin<ref name="pubmed-11501051">https://www.ncbi.nlm.nih.gov/pubmed/11501051</ref>
|Liquiritigenin<ref name="pubmed-11501051">{{cite journal | vauthors=((Pan, X.)), ((Kong, L. D.)), ((Zhang, Y.)), ((Cheng, C. H.)), ((Tan, R. X.)) | journal=Acta Pharmacologica Sinica | title=In vitro inhibition of rat monoamine oxidase by liquiritigenin and isoliquiritigenin isolated from Sinofranchetia chinensis | volume=21 | issue=10 | pages=949–953 | date= October 2000 | issn=1671-4083}}</ref>
|MAO-A, MAO-B
|MAO-A, MAO-B
|-
|-
Line 279: Line 117:
|-
|-
|[[Myristica fragrans (botany)|Nutmeg (''Myristica fragrans'')]]
|[[Myristica fragrans (botany)|Nutmeg (''Myristica fragrans'')]]
|Kaempferol<ref>https://www.ncbi.nlm.nih.gov/pubmed/26821152</ref>
|Kaempferol<ref>{{cite journal | vauthors=((Gidaro, M. C.)), ((Astorino, C.)), ((Petzer, A.)), ((Carradori, S.)), ((Alcaro, F.)), ((Costa, G.)), ((Artese, A.)), ((Rafele, G.)), ((Russo, F. M.)), ((Petzer, J. P.)), ((Alcaro, S.)) | journal=Journal of Agricultural and Food Chemistry | title=Kaempferol as Selective Human MAO-A Inhibitor: Analytical Detection in Calabrian Red Wines, Biological and Molecular Modeling Studies | volume=64 | issue=6 | pages=1394–1400 | date=17 February 2016 | issn=1520-5118 | doi=10.1021/acs.jafc.5b06043}}</ref>
|MAO-A
|MAO-A
|-
|-
|[[Myristica fragrans (botany)|Nutmeg (''Myristica fragrans'')]]
|[[Myristica fragrans (botany)|Nutmeg (''Myristica fragrans'')]]
|[[Myristicin]]
|[[Myristicin]]
|MAO-A, MAO-B?<ref>https://www.ncbi.nlm.nih.gov/pubmed/5615547</ref>
|MAO-A, MAO-B?<ref>{{cite journal | vauthors=((Truitt, E. B.)) | journal=Psychopharmacology Bulletin | title=The pharmacology of myristicin and nutmeg | volume=4 | issue=3 | pages=14 | date= December 1967 | issn=0048-5764}}</ref>
|-
|-
|[[Myristica fragrans (botany)|Nutmeg (''Myristica fragrans'')]]
|[[Myristica fragrans (botany)|Nutmeg (''Myristica fragrans'')]]
|Quercetin<ref>https://www.ncbi.nlm.nih.gov/pubmed/23009399</ref>
|Quercetin<ref>{{cite journal | vauthors=((Bandaruk, Y.)), ((Mukai, R.)), ((Kawamura, T.)), ((Nemoto, H.)), ((Terao, J.)) | journal=Journal of Agricultural and Food Chemistry | title=Evaluation of the inhibitory effects of quercetin-related flavonoids and tea catechins on the monoamine oxidase-A reaction in mouse brain mitochondria | volume=60 | issue=41 | pages=10270–10277 | date=17 October 2012 | issn=1520-5118 | doi=10.1021/jf303055b}}</ref>
|MAO-A
|MAO-A
|-
|''Nicotiana tabacum'' (cultivated tobacco)
|[[Harmane]]<ref name="Poindexter">{{cite journal | last=Poindexter | first=E.H. | last2=Carpenter | first2=R.D. | title=The isolation of harmane and norharmane from tobacco and cigarette smoke | journal=Phytochemistry | volume=1 | issue=3 | year=1962 | issn=0031-9422 | doi=10.1016/s0031-9422(00)82825-3 | pages=215–221}}</ref>
|MAO-A<ref name="pmid35832393" /><ref name="harman" />
|-
|-
|Passionflower (''Passiflora incarnata''), weak MAOI
|Passionflower (''Passiflora incarnata''), weak MAOI
Line 296: Line 138:
|Passionflower (''Passiflora incarnata''), weak MAOI
|Passionflower (''Passiflora incarnata''), weak MAOI
|[[Harmine]]
|[[Harmine]]
|MAO-A, MAO-B
|[[RIMA]]
|-
|-
|Passionflower (''Passiflora incarnata''), weak MAOI
|Passionflower (''Passiflora incarnata''), weak MAOI
Line 305: Line 147:
|Quercetin
|Quercetin
|MAO-A
|MAO-A
|-
|''Rhodiola rosea''
|
|MAO-A, MAO-B<ref>https://www.ncbi.nlm.nih.gov/pubmed/19168123</ref>
|-
|-
|[[Peganum_harmala#Chemistry|Syrian rue (''Peganum harmala'')]]
|[[Peganum_harmala#Chemistry|Syrian rue (''Peganum harmala'')]]
Line 315: Line 153:
|-
|-
|[[Peganum_harmala#Chemistry|Syrian rue (''Peganum harmala'')]]
|[[Peganum_harmala#Chemistry|Syrian rue (''Peganum harmala'')]]
|[[Harman]]
|[[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, MAO-B<ref name="harman" />
|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 -->
|-
|-
|[[Peganum_harmala#Chemistry|Syrian rue (''Peganum harmala'')]]
|[[Peganum_harmala#Chemistry|Syrian rue (''Peganum harmala'')]]
|[[Harmine]]
|[[Harmine]]
|MAO-A, MAO-B
|[[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="Monoamine oxidases and tobacco smoking." />
|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="Monoamine oxidases and tobacco smoking.">https://www.ncbi.nlm.nih.gov/pubmed/11343627</ref>
|1,2,3,4-tetrahydroisoquinoline<ref name="Berlin2001" />
|MAO-A, MAO-B
|MAO-A, MAO-B
|-
|-
|[[Nicotiana (botany)|Tobacco]]
|[[Nicotiana (botany)|Tobacco]]
|[[Harman]]<ref name="Tobacco">https://www.sciencedirect.com/science/article/pii/S0161813X16302625</ref>
|[[Harmane]]<ref name="Tobacco">{{cite journal | vauthors=((Truman, P.)), ((Grounds, P.)), ((Brennan, K. A.)) | journal=NeuroToxicology | title=Monoamine oxidase inhibitory activity in tobacco particulate matter: Are harman and norharman the only physiologically relevant inhibitors? | volume=59 | pages=22–26 | date=1 March 2017 | url=https://www.sciencedirect.com/science/article/pii/S0161813X16302625 | issn=0161-813X | doi=10.1016/j.neuro.2016.12.010}}</ref>
|MAO-A, MAO-B<ref name="harman" />
|MAO-A<ref name="pmid35832393" /><ref name="harman" />
|-
|-
|[[Nicotiana (botany)|Tobacco]]
|[[Nicotiana (botany)|Tobacco]]
|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
|-
|-
|}
|}


*Psychedelics
*Psychedelics
**[[AET]]<ref name="Shulgin MAOI">https://erowid.org/chemicals/amt/amt_info1.shtml</ref>
**[[AET]]<ref name="Shulgin MAOI">{{Citation | title=Erowid AMT Vault : Information on AMT as an MAOI | url=https://erowid.org/chemicals/amt/amt_info1.shtml}}</ref>
**[[AMT]]<ref name="Shulgin MAOI" />
**[[AMT]]<ref name="Shulgin MAOI" />
*Pharmaceuticals
*Pharmaceuticals
Line 351: Line 197:
**Non-hydrazines
**Non-hydrazines
***Tranylcypromine (Parnate, Jatrosom)
***Tranylcypromine (Parnate, Jatrosom)
**β-Carbolines
***[[9-Me-BC]]
====''Banisteriopsis caapi''====
The highly urban Brazilian ayahuasca church União do Vegetal (UDV)'s preparation of ayahuasca contains only two ingredients: ''Banisteriopsis caapi'' (MAOI carrier) and ''Psychotria viridis'' (DMT carrier). Dietary restrictions are not used by the UDV, suggesting the risk is much lower than perceived and probably non-existent.<ref name="Jonathan Ott, 1994">{{cite book |last1=Ott |first1= J. |title=Ayahuasca Analogues: Pangaean Entheogens |location=Kennewick, WA |publisher=Natural Books |year=1994 |isbn=978-0-9614234-4-5}}</ref>


===Selective MAO-A inhibitors===
===Selective MAO-A inhibitors===
Line 356: Line 207:


*Naturally occurring sources
*Naturally occurring sources
**Betel nut (''Areca catechu''): MAO-A inhibitor.<ref>https://www.ncbi.nlm.nih.gov/pubmed/23195244</ref><ref name="Monoamine oxidases and tobacco smoking." />
**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>https://www.ncbi.nlm.nih.gov/pubmed/28302559</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 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" />
**[[Bromo-DragonFLY]] (suspected, very strong)<ref>https://www.ncbi.nlm.nih.gov/pubmed/30036687</ref>
***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>
***Dangerous to combine with MAOIs.
*Pharmaceuticals
*Pharmaceuticals
**Bifemelane (Alnert, Celeport) (available in Japan)
**Bifemelane (Alnert, Celeport) (available in Japan)
Line 372: Line 226:
===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>https://www.ncbi.nlm.nih.gov/pubmed/9832350</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>
**Olives (''Olea europaea''), fresh, olive leaf extract: The selective MAO-B inhibitor hydroxytyrosol.<ref>https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5125943** Tea (''Camellia sinensis''), black tea, green tea, white tea, oolong tea: The selective MAO-B inhibitors catechin, and epicatechin
**Olives (''Olea europaea''), fresh, olive leaf extract: The selective MAO-B inhibitor hydroxytyrosol.<ref>{{cite journal | vauthors=((Goldstein, D. S.)), ((Jinsmaa, Y.)), ((Sullivan, P.)), ((Holmes, C.)), ((Kopin, I. J.)), ((Sharabi, Y.)) | journal=Neurochemical research | title=3,4-Dihydroxyphenylethanol (Hydroxytyrosol) Mitigates the Increase in Spontaneous Oxidation of Dopamine during Monoamine Oxidase Inhibition in PC12 Cells | volume=41 | issue=9 | pages=2173–2178 | date= September 2016 | url=https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5125943/ | issn=0364-3190 | doi=10.1007/s11064-016-1959-0}}</ref>
/?tool=pmcentrez</ref>
*Pharmaceuticals
*Pharmaceuticals
**Rasagiline (Azilect)
**Rasagiline (Azilect)
Line 381: Line 234:


===Unknown selectivity===
===Unknown selectivity===
*Psychedelics
*Psychedelics
**[[5-MeO-AET]]
**[[5-MeO-AET]]
Line 393: Line 245:
**[[PMEA]]
**[[PMEA]]
**[[4-HO-DTBT]]
**[[4-HO-DTBT]]
==Toxicity and harm potential==
{{Information/MAOIs and RIMAs}}
When the CYP450 system is impacted in this way, it leads to higher levels of certain drugs in your system at one time. This can cause unwanted side effects, and sometimes, an overdose.
===Dangerous interactions===
{{DangerousInteractions/Intro}}
{{DangerousInteractions/MAOIs}}
====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:
**[[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 pachanoi|San Pedro cactus (''Echinopsis pachanoi'' (syn. ''Trichocereus pachanoi''))]]<ref>{{cite journal|author1=Crosby, D.M. |author2=McLaughlin, J.L.|title=Cactus Alkaloids. XIX Crystallization of Mescaline HCl and 3-Methoxytyramine HCl from Trichocereus panchanoi| journal=Lloydia and the Journal of Natural Products| date=Dec 1973 |volume=36 |issue=4 |pages=416–418 |pmid=4773270 |url=http://catbull.com/alamut/Bibliothek/1973_d.m._crosby_8158_1.pdf |accessdate=13 December 2013}}</ref>
**Other cactis:
{| class="wikitable sortable" border="1" style="font-size:smaller"
|-
!Specie
!Tyramine (mg/gram of alive plant)<ref name="Grym">{{cite book | vauthors=((Grym, R.)) | date= 1997 | title=Rod Lophophora: = Die Gattung Lophophora | publisher=Stanik [u.a.] | isbn=9788090093393}}</ref>
|-
|''[[Lophophora williamsii (botany)|L. williamsii]]''
!0.5 - 1
|-
|''[[Lophophora jourdaniana (botany)|L. jourdaniana]]''
!0.6
|-
|''[[Lophophora diffusa (botany)|L. diffusa]]''
!0.1
|-
|''[[Lophophora fricii (botany)|L. fricii]]''
!0.1
|-
|''[[Lophophora koehresii (botany)|L. koehresii]]''
!0.1
|-
|}
====Psychoactive substances====
The MAOIs are well-known for their numerous drug interactions, including the following kinds of substances:
*Substances that are metabolized by monoamine oxidase, as they can be boosted by up to several-fold
*Substances that increase serotonin, noradrenaline, or dopamine activity as too much of any of these neurotransmitters can result in severe acute consequences including [[serotonin syndrome]], hypertensive crisis, and psychosis.
====By chemicals====
*Amino acids, and amino acid metabolism metabolic intermediates
**Monoamine precursors
***[[5-HTP]] → serotonin
***<small>L</small>-DOPA → dopamine, and epinephrine (adrenaline)
***L-phenylalanine → L-tyrosine, and phenethylamine: Use with caution,<ref>{{cite web |last1=Metcalf |first1=Eric |title=Phenylalanine: Uses and Risks |url=https://www.webmd.com/vitamins-and-supplements/phenylalanine-uses-and-risks |website=WebMD |language=en}}</ref> taking phenylalanine while taking MAOIs may cause a severe increase in blood pressure (hypertensive crisis).<ref>{{cite web |title=Phenylalanine |url=http://slu.adam.com/content.aspx?productid=107&pid=33&gid=000318 |website=slu.adam.com |language=en}}</ref>
***L-tryptophan → 5-HTP, and melatonin: May result in short-term serotonin syndrome.<ref name="Boyer-NEJM">{{cite journal | vauthors = Boyer EW, Shannon M | title = The serotonin syndrome | journal = The New England Journal of Medicine | volume = 352 | issue = 11 | pages = 1112–20 | date = March 2005 | pmid = 15784664 | doi = 10.1056/NEJMra041867 | url = https://semanticscholar.org/paper/bd6134bea06b830b36b696ffd7b34b395f6f72ec }}</ref>
***L-tyrosine → L-DOPA, and tyramine: It is unknown if MAOIs interact with tyrosine, so use with caution.<ref>{{cite web |title=Tyrosine: Benefits, Side Effects and Dosage |url=https://www.healthline.com/nutrition/tyrosine |website=Healthline |language=en |date=1 February 2018}}</ref>
**Amino acid metabolism metabolic intermediates
***[[SAM-e]] → epinephrine (adrenaline)
*[[Adrenergic]]s
*[[Lysergamides]]: [[LSA]] ([[morning glory]]: (''[[Argyreia nervosa]]'', ''[[Ipomoea tricolor]]'', etc)<ref>{{Citation | title=Erowid Morning Glory Vault: Basics | url=https://www.erowid.org/plants/morning_glory/morning_glory_basics.shtml}}</ref>
*[[Monoaminergic]]s (MA)
**[[Cholinergic]]s (see also MAOIs that act as [[Talk:Acetylcholinesterase_inhibitor|acetylcholinesterase inhibitor]]s (AChEIs)), certain substances, examples: [[alpha-GPC|''alpha''-GPC]] (suspected monoaminergic),<ref name="Alpha-GPC and citicoline">{{cite journal | vauthors=((Tayebati, S. K.)), ((Tomassoni, D.)), ((Nwankwo, I. E.)), ((Di Stefano, A.)), ((Sozio, P.)), ((Cerasa, L. S.)), ((Amenta, F.)) | journal=CNS & neurological disorders drug targets | title=Modulation of monoaminergic transporters by choline-containing phospholipids in rat brain | volume=12 | issue=1 | pages=94–103 | date=1 February 2013 | issn=1996-3181 | doi=10.2174/1871527311312010015}}</ref><ref>{{cite journal | vauthors=((Trabucchi, M.)), ((Govoni, S.)), ((Battaini, F.)) | journal=Il Farmaco; Edizione Scientifica | title=Changes in the interaction between CNS cholinergic and dopaminergic neurons induced by L-alpha-glycerylphosphorylcholine, a cholinomimetic drug | volume=41 | issue=4 | pages=325–334 | date= April 1986 | issn=0430-0920}}</ref> [[centrophenoxine]],<ref name="Effect of centrophenoxine, piracetam and aniracetam on the monoamine oxidase activity in different brain structures of rats" /> [[citicoline]] (suspected monoaminergic)<ref name="Alpha-GPC and citicoline" /><ref>{{cite journal | vauthors=((Secades, J. J.)), ((Lorenzo, J. L.)) | journal=Methods and Findings in Experimental and Clinical Pharmacology | title=Citicoline: pharmacological and clinical review, 2006 update | volume=28 Suppl B | pages=1–56 | date= September 2006 | issn=0379-0355}}</ref>
**[[#List of MAOIs|MAOI]]s, avoid mixing pure MAOIs. Plants with multiple MAOIs like ''Peganum harmala'' are fine since they have been evaluated.
***[[RIMA]]s
*Disinhibitors
**Norepinephrine and dopamine disinhibitors (NDDIs): [[Fluoxetine]]
*Opioids: Some opioid analgesics are associated with a risk of serotonin syndrome in combination with MAOIs due to their serotonergic properties. Other combinations may result in opioid toxicity due to CYP450 enzyme inhibition by the MAOI. Given the widespread availability of several suitable alternative drugs, the combination of dextromethorphan, methadone, pethidine, tramadol, fentanyl or tapentadol with an MAOI should usually be avoided, including in the 14 day period following the withdrawal of an irreversible MAOI. Morphine, codeine, oxycodone and buprenorphine are alternative opioids for patients receiving MAOIs, though starting at a low dose and titrating cautiously against clinical response is advised.<ref>https://www.sps.nhs.uk/articles/what-is-the-risk-of-interaction-between-opioids-and-monoamine-oxidase-inhibitors-maois/</ref>
*[[Racetam]]s: [[Aniracetam]],<ref name="Effect of centrophenoxine, piracetam and aniracetam on the monoamine oxidase activity in different brain structures of rats">{{cite journal | vauthors=((Stancheva, S. L.)), ((Alova, L. G.)) | journal=Farmakologiia I Toksikologiia | title=[Effect of centrophenoxine, piracetam and aniracetam on the monoamine oxidase activity in different brain structures of rats] | volume=51 | issue=3 | pages=16–18 | date= June 1988 | issn=0014-8318}}</ref> [[piracetam]]<ref name="Effect of centrophenoxine, piracetam and aniracetam on the monoamine oxidase activity in different brain structures of rats" />
*Receptor agonists
**Serotonin receptor agonist
***5-HT<sub>1A</sub>: [[CBD]]<ref name="pmid16258853">{{cite journal | vauthors = Russo EB, Burnett A, Hall B, Parker KK | title = Agonistic properties of cannabidiol at 5-HT1a receptors | journal = Neurochemical Research | volume = 30 | issue = 8 | pages = 1037–43 | date = August 2005 | pmid = 16258853 | doi = 10.1007/s11064-005-6978-1 }}</ref>
**Dopamine receptor agonist, examples: amphetamines ([[amphetamine]], [[lisdexamfetamine]], [[methamphetamine]]), [[cathinone]], [[cocaine]], [[PCP]], [[phenethylamine]], [[salvinorin A]] (found in ''[[Salvia divinorum]]''),<ref>{{cite journal | vauthors=((Seeman, P.)), ((Guan, H.-C.)), ((Hirbec, H.)) | journal=Synapse | title=Dopamine D2 High receptors stimulated by phencyclidines, lysergic acid diethylamide, salvinorin A, and modafinil | volume=63 | issue=8 | pages=698–704 | date= August 2009 | url=https://onlinelibrary.wiley.com/doi/10.1002/syn.20647 | issn=08874476 | doi=10.1002/syn.20647}}</ref> [[tyramine]]
***D2: [[CBD]],<ref>{{cite journal | vauthors=((Seeman, P.)) | journal=Translational Psychiatry | title=Cannabidiol is a partial agonist at dopamine D2High receptors, predicting its antipsychotic clinical dose | volume=6 | issue=10 | pages=e920 | date= October 2016 | url=https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5315552/ | issn=2158-3188 | doi=10.1038/tp.2016.195}}</ref>
*[[Releasing agent]]s and monoamine releasing agent (MRA) (or monoamine releaser)
**Dopamine releasing agent (DRA)
**Norepinephrine releasing agent (NRA) (or adrenergic releasing agent), examples: [[Adrenaline]], [[ephedrine]], [[pseudoephedrine]]
**Norepinephrine-dopamine releasing agents (NDRAs), examples: [[Amphetamine]], [[cathinone]], [[phenethylamine]], [[tyramine]], [[methamphetamine]]
**Serotonin releasing agent (SRA)
***[[Dextropropoxyphene]]
***[[Diphenhydramine]]
***[[DXM]]
***Selective serotonin releasing agent (SSRA), examples: [[MDAI]], [[PMA]], [[PMMA]]
**Serotonin–norepinephrine-dopamine releasing agent (SNDRA) (also known as a triple releasing agent (TRA)), examples:
***Amphetamines: [[MDA]], [[MDMA]], [[methamphetamine]]
***Substituted benzofurans: [[5-APB]], [[6-APB]]
***Substituted cathinones: [[mephedrone]]
***Tryptamines: [[αET]], [[αMT]]
*[[Reuptake inhibitor]]s and monoamine reuptake inhibitors (MRIs)
**Dopamine reuptake inhibitors (DRI), examples: [[Armodafinil]], [[ethylphenidate]], [[methylphenidate]], [[modafinil]]
**Norepinephrine reuptake inhibitor (NRI, NERI) (or adrenergic reuptake inhibitor (ARI)), example: [[Tapentadol]]
**Norepinephrine-dopamine reuptake inhibitors (NDRI), examples: [[Ethylphenidate]], [[methylphenidate]], [[prolintane]]. Suspected: [[A-PVP]], [[desoxypipradrol]], [[MDPV]]
**Serotonin reuptake inhibitor (SRA)
***[[Selective serotonin reuptake inhibitor]]s (SSRI), examples: [[Selective_serotonin_reuptake_inhibitor#Citalopram|Citalopram]], [[Selective_serotonin_reuptake_inhibitor#escitalopram|escitalopram]], [[Selective_serotonin_reuptake_inhibitor#Fluoxetine|fluoxetine]], [[Selective_serotonin_reuptake_inhibitor#Fluvoxamine|fluvoxamine]], [[Selective_serotonin_reuptake_inhibitor#Paroxetine|paroxetine]], [[Selective_serotonin_reuptake_inhibitor#Sertraline|sertraline]]
**Serotonin–norepinephrine–dopamine reuptake inhibitor (SNDRI), also known as a triple reuptake inhibitor (TRI), examples:
***[[6-APB]]
***[[Cocaine]]
***[[Ketamine]]
***[[PCP]]
***St. Johnswort (''Hypericum perforatum'')
*Serotonin modulator and stimulator (SMS)
*[[Substituted cathinone]]s, examples: [[a-PVP]], [[MDPV]], [[methylone]], [[mephedrone]]
*[[Substituted phenethylamines]]
**[[Amphetamines]], examples: [[Amphetamine]], [[dextroamphetamine]], [[methamphetamine]]
**Psychedelic phenethylamines, examples: [[2C-x]] (and NBs for example [[25x-NBOH]], [[25x-NBOMe]]), [[DOx]], [[MDMA]], [[mescaline]] ([[psychedelic cacti]])
*[[Tryptamine#List_of_substituted_tryptamines|Substituted tryptamines]], examples:
**5-MeO-''xx''T: [[5-MeO-AMT]],<ref>{{Citation | title=Erowid 5-MeO-AMT Vault: Basics | url=https://erowid.org/chemicals/5meo_amt/5meo_amt_basics.shtml}}</ref> [[5-MeO-DiPT]],<ref name="The effects of non-medically used psychoactive drugs on monoamine neurotransmission in rat brain">{{cite journal | vauthors=((Nagai, F.)), ((Nonaka, R.)), ((Satoh Hisashi Kamimura, K.)) | journal=European Journal of Pharmacology | title=The effects of non-medically used psychoactive drugs on monoamine neurotransmission in rat brain | volume=559 | issue=2–3 | pages=132–137 | date=22 March 2007 | issn=0014-2999 | doi=10.1016/j.ejphar.2006.11.075}}</ref> [[5-MeO-DMT]],<ref name="The effects of non-medically used psychoactive drugs on monoamine neurotransmission in rat brain" /><ref>{{Citation | title=Erowid 5-MeO-DMT Vault : Health | url=https://erowid.org/chemicals/5meo_dmt/5meo_dmt_health.shtml}}</ref> [[5-MeO-MiPT]]<ref name="The effects of non-medically used psychoactive drugs on monoamine neurotransmission in rat brain" /><ref>{{Citation | title=Erowid 5-MeO-MIPT Vault: Basics | url=https://erowid.org/chemicals/5meo_mipt/5meo_mipt_basics.shtml}}</ref>
*Tetracyclic antidepressants (TeCA), example: [[Mirtazapine]]
*Tricyclic antidepressants (TCA), example: [[Tianeptine]]
*[[Tropane alkaloids]]
**Anticholinergics (found in (''[[Datura]] spp.'', ''[[Hyoscyamus niger (botany)|Hyoscyamus niger]]'', etc)<ref>{{Citation | title=Erowid Datura Vaults : Datura FAQ | url=https://www.erowid.org/plants/datura/datura_faq.shtml}}</ref>)
***[[Atropine]]
***[[Hyoscyamine]]
***[[Scopolamine]]
**Stimulants
***[[Cocaine]]
***[[RTI-111]]
*[[Xanthine]]s: Caffeine<ref>https://www.jwatch.org/fw108796/2014/05/06/severe-hypertension-linked-caffeine-mao-inhibitor</ref>
====By pharmacotherapy====
*Antibiotics
**Linezolid
*Anticholinergics
**Hyoscine, also known as scopolamine: The transdermal patch (''e.g.,'' Transderm Scōp) for prevention of nausea and motion sickness employs hyoscine base, and is effective for up to three days.<ref>{{cite web |url = http://www.transdermscop.com/prescribing-information.htm |title = Transderm Scop patch prescribing information |archive-url = https://web.archive.org/web/20090204034217/http://www.transdermscop.com/prescribing-information.htm |archive-date = 4 February 2009 |df = dmy-all }}</ref>
*Antihistamines (allergy medicines used to treat allergic conjunctivitis most often caused by hay fever), for example desloratadine, and loratadine. MAOI safe alternative: [https://go.drugbank.com/drugs/DB01003 Cromoglicic acid] eye drops.
*Antitussives
**Cold medicine
*Decongestants
**[[Naphazoline]]
*Essential nutrients
**Choline
***Certain cholinergics (see "Cholinergics")
*Local and general anesthetic
*Vasoconstrictors
**[[Naphazoline]] (brand name Clear Eyes, Cleari -- Eye drops used to treat red eyes, caused by for example [[cannabis]] that induces corneal vasodilation)
====Over-the-counter (OTC) medicines====
====Tyramine====
Tyramine is physiologically metabolized by monamine oxidases (primarily MAO-A), FMO3, PNMI, DBH and CYP2D6.<ref>https://www.ajol.info/index.php/jomip/article/view/213795</ref><ref>https://pubmed.ncbi.nlm.nih.gov/31736764/</ref> Tyramine and dopamine are metabolized by both MAO-A and MAO-B. It has been established that hypertensive crises are a consequence of MAO-A inhibition (Youdim et al. 1988; Laux et al. 1995).<ref>https://pubmed.ncbi.nlm.nih.gov/10063483/</ref> However, eating foods rich in tyramine while taking high doses of MAO-B inhibitors can cause a sudden increase in blood pressure.<ref>https://www.parkinsons.org.uk/information-and-support/mao-b-inhibitors-rasagiline-selegiline-safinamide</ref>
Tyramine causes hypertensive crises after MAO inhibition aka the "cheese effect" or "cheese crisis". Using a MAO inhibitor (MAOI), the intake of approximately 10 to 25 mg of tyramine is required for a severe reaction compared to 6 to 10 mg for a mild reaction.<ref>{{cite journal | vauthors=((Sathyanarayana Rao, T. S.)), ((Yeragani, V. K.)) | journal=Indian Journal of Psychiatry | title=Hypertensive crisis and cheese | volume=51 | issue=1 | pages=65–66 | date= 2009 | url=https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2738414/ | issn=0019-5545 | doi=10.4103/0019-5545.44910}}</ref> Tyramine rich food should also be avoided by people prone to headache and migraine.
=====Tyramine rich foods=====
Specific foods with high amounts of [[tyramine]]:<ref name="Kathrynne">https://www.mc.vanderbilt.edu/documents/neurology/files/Tyramine%20Menu%20Book%2006227101.pdf</ref><ref name="Estimates of maximum tolerable levels of tyramine content in foods in Austria" /><ref>{{cite journal | vauthors=((McCabe-Sellers, B. J.)), ((Staggs, C. G.)), ((Bogle, M. L.)) | journal=Journal of Food Composition and Analysis | title=Tyramine in foods and monoamine oxidase inhibitor drugs: A crossroad where medicine, nutrition, pharmacy, and food industry converge | volume=19 | pages=S58–S65 | date= August 2006 | url=https://linkinghub.elsevier.com/retrieve/pii/S0889157505001444 | issn=08891575 | doi=10.1016/j.jfca.2005.12.008}}</ref>
*Aged cheese (gouda, camembert, cheddar) -- Few cheeses (even. 'mature' cheeses) contain more than 25 mg of tyramine in 100 grams.<ref>https://psychotropical.info/wp-content/uploads/2018/02/MAOI_diet_drug_interactions_2017.pdf</ref> However, Stilton (a blue cheese) contains up to 217 mg tyramine per 100 grams.<ref name="Kathrynne" />
*Aged, smoked or pickled meats
*Aged or fermented soy and yeast products (soy sauce, teriyaki sauce, home baked yeast bread, sourdough bread)
*Overripe fruits
*High amounts of nuts
Candy, and dried fruit:
*[[Cocoa#Chemistry|Cocoa]]
**[[Chocolate milk]]
**Chocolate, especially dark chocolate
**Dried and/or candied fruit rolled in cocoa powder
*Licorice (isoliquiritigenin and liquiritigenin are [[#Nonselective_MAO-A_and_MAO-B_inhibitors|non-selective MAOIs]]).<ref name="pubmed-11501051" />
**Licorice candy
**Dried and/or candied fruit rolled in licorice powder
Tyramine formation has been associated with bacterial contamination of foods or temperature abuse conditions, but can also occur as a side effect of generally desired ripening processes.<ref name="Estimates of maximum tolerable levels of tyramine content in foods in Austria">{{cite journal | vauthors=((Paulsen, P.)), ((Grossgut, R.)), ((Bauer, F.)), ((Rauscher-Gabernig, E.)) | journal=Journal of Food and Nutrition Research (Slovak Republic) | title=Estimates of maximum tolerable levels of tyramine content in foods in Austria | date= 2012 | url=https://agris.fao.org/agris-search/search.do?recordID=SK2012000039}}</ref> Tyramine is a breakdown product of the amino acid L-tyrosine.
==Reduced bio-availability==
===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.
===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>


===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>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]]
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==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)]
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[[Category:Cytochrome P450 inhibitor]]
[[Category:Cytochrome P450 inhibitor]]
[[Category:Pharmacology]]
[[Category:Pharmacology]]
{{#set:Featured=true}}
Retrieved from "https://psy.st/wiki/MAOI"