MAOI: Difference between revisions

{{For|reversible inhibitor of monoamine oxidase A|RIMA}}

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.  

===Reversibility===

==Consumption planning for MAOIs==

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===

*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.

*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>{{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>

*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>

==Poly drug use==

*[[Ayahuasca]]: The [[tryptamine]] [[DMT]] will break down without MAOIs when taken orally.

==List of MAOIs==

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

===Nonselective MAOIs/RIMAs===

*Naturally occurring sources

!Natural occuring source

!Chemical

|-

|''[[Banisteriopsis caapi#Chemistry|Banisteriopsis caapi]]'' (ayahuasca, caapi or yagé)

|[[RIMA]]

|-

|[[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" />

|[[Cannabis#Chemistry|Cannabis]], Cannabis extract

|

|-

|[[Cocoa]] bean (from ''Theobroma cacao'')

|-

|[[Cocoa]] bean (from ''Theobroma cacao'')

|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'')

|MAO-B<ref name="Catechin, and epicatechin" />

|-

|[[Cocoa]] bean (from ''Theobroma cacao'')

|

|-

|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

|-

|Passionflower (''Passiflora incarnata''), weak MAOI

|Quercetin

|MAO-A

|-

|[[Peganum_harmala#Chemistry|Syrian rue (''Peganum harmala'')]]

|-

|[[Peganum_harmala#Chemistry|Syrian rue (''Peganum harmala'')]]

|-

|[[Peganum_harmala#Chemistry|Syrian rue (''Peganum harmala'')]]

|[[Harmine]]

|[[RIMA]]

|-

|[[Nicotiana (botany)|Tobacco]]

|MAO-A, MAO-B

|-

|[[Nicotiana (botany)|Tobacco]]

|MAO-A, MAO-B

|-

|Norharman<ref name="Tobacco" />

|MAO-A, MAO-B<ref name="norharman" />

|-

|}

**Non-hydrazines

***Tranylcypromine (Parnate, Jatrosom)

===Selective MAO-A inhibitors===

*Naturally occurring sources

**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

**[[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-7]] (suspected, strong)<ref name="2C-T-2 and 2C-T-7" />

**[[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>

*Pharmaceuticals

**Bifemelane (Alnert, Celeport) (available in Japan)

===Unknown selectivity===

*Psychedelics

**[[5-MeO-AET]]

==Toxicity and harm potential==

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.

*[[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:

|}

The MAOIs are well-known for their numerous drug interactions, including the following kinds of substances:

====By chemicals====

*Amino acids, and amino acid metabolism metabolic intermediates

**Monoamine precursors

====By pharmacotherapy====

*Antibiotics

**Linezolid

====Over-the-counter (OTC) medicines====

==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===

*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>

==See also==

*[[Responsible use]]

*[[RIMA]]

==External links==

*[https://en.wikipedia.org/wiki/Monoamine_oxidase_inhibitor Monoamine oxidase inhibitor (Wikipedia)]

*[https://en.wikipedia.org/wiki/Monoamine_oxidase_A Monoamine oxidase A (Wikipedia)]

[[Category:Cytochrome P450 inhibitor]]

[[Category:Pharmacology]]