MAOI

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Always check if your MAOIs also inhibit other substances. Most MAOIs are also cytochrome P450 inhibitors and some are also acetylcholinesterase inhibitors (AChEIs)

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, see 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.[1] They are also used in the treatment of social anxiety, Parkinson's disease and several other disorders.[2]

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.

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

Further information: RIMA

The early MAOIs inhibit monoamine oxidase irreversibly, meaning they permanently deactivate it and the enzyme cannot function until it has been replaced by the body, which can take about two weeks. A few newer MAOIs, known as reversible inhibitors of monoamine oxidase A (RIMAs), are reversible. This means that they are able to detach from the enzyme to facilitate usual catabolism of the substrate.[citation needed]

Consumption planning for MAOIs

Commons-emblem-notice.svg See the 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).

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).[3] A chronic meth user might still test positive seven to 10 days after consuming the drug.
  • Pharmacotherapy examples
    • Cannabinoids: Cannabinoids are lipophilic. For example, THC has been detected in heavy cannabis users after 77 days of drug abstinence (Ellis et al., 1985).[4]
    • 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).[5]
  • Tolerance from heavy substance use or therapy may cause 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.[6][7]

After MAOI consumption

MAOIs cause dangerous interactions with many substances, they must be avoided during or within 14 days of administration of monoamine oxidase inhibitors.

Poly drug use

List of MAOIs

See also: RIMA § List of RIMAs

Party pills (sometimes called "herbal highs") often contain MAOIs.

Nonselective MAOIs/RIMAs

See also naturally occurring RIMA sources.

  • Naturally occurring sources
Natural occuring source Chemical MAOI type
Banisteriopsis caapi (ayahuasca, caapi or yagé) (−)-epicatechin[8] MAO-B
Banisteriopsis caapi (ayahuasca, caapi or yagé) (−)-procyanidins[8] MAO-B
Banisteriopsis caapi (ayahuasca, caapi or yagé) Harmaline[8] RIMA
Banisteriopsis caapi (ayahuasca, caapi or yagé) Harmine[8] RIMA
Camellia sinensis (tea plant) Harmane[9] MAO-A[10][11]
Black pepper (Piper nigrum) Piperine[12] MAO-A, MAO-B
Cannabis, Cannabis extract MAO-A, MAO-B[13]
Cocoa bean (from Theobroma cacao) Caffeine[14] MAO-A, MAO-B[15]
Cocoa bean (from Theobroma cacao) Catechin[14][16] MAO-B[17]
Cocoa bean (from Theobroma cacao) Epicatechin[14][16] MAO-B[17]
Cocoa bean (from Theobroma cacao) Tetrahydro-beta-carbolines[14]
Coffee (Coffea arabica, Coffea canephora) Caffeine MAO-A, MAO-B[15]
Coffee (Coffea arabica, Coffea canephora) Harmane[18] MAO-A[10][11]
Coffee (Coffea arabica, Coffea canephora) Norharman[18] MAO-A, MAO-B[19]
Liquorice/licorice (Glycyrrhiza Glabra) Isoliquiritigenin[20] MAO-A, MAO-B
Liquorice/licorice (Glycyrrhiza Glabra) Liquiritigenin[20] MAO-A, MAO-B
Long pepper (Piper longum) Piperine[12] MAO-A, MAO-B
Nutmeg (Myristica fragrans) Kaempferol[21] MAO-A
Nutmeg (Myristica fragrans) Myristicin MAO-A, MAO-B?[22]
Nutmeg (Myristica fragrans) Quercetin[23] MAO-A
Nicotiana tabacum (cultivated tobacco) Harmane[24] MAO-A[10][11]
Passionflower (Passiflora incarnata), weak MAOI Apigenin MAO-A
Passionflower (Passiflora incarnata), weak MAOI Harmine RIMA
Passionflower (Passiflora incarnata), weak MAOI Kaempferol MAO-A
Passionflower (Passiflora incarnata), weak MAOI Quercetin MAO-A
Syrian rue (Peganum harmala) Harmaline RIMA
Syrian rue (Peganum harmala) Harmane[25] MAO-A[10][11]
Syrian rue (Peganum harmala) Harmine RIMA
Rhodiola rosea (rose root) MAO-A, MAO-B[26]
Tobacco 1,2,3,4-tetrahydro-b-carboline (THbC)[13] MAO-A, MAO-B
Tobacco 1,2,3,4-tetrahydroisoquinoline[13] MAO-A, MAO-B
Tobacco Harmane[27] MAO-A[10][11]
Tobacco Norharman[27] MAO-A, MAO-B[19]
Turmeric Curcumin[28] MAO-B
  • Psychedelics
  • Pharmaceuticals
    • Hydrazines (antidepressant)
      • Isocarboxazid (Marplan)
      • Nialamide (Niamid)
      • Phenelzine (Nardil, Nardelzine)
      • Hydracarbazine
    • Non-hydrazines
      • Tranylcypromine (Parnate, Jatrosom)
    • β-Carbolines

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.[30]

Selective MAO-A inhibitors

For safer MAO-A inhibitors, see RIMA.
  • Naturally occurring sources
  • Psychedelics
    • 2C-T-2 (suspected, weak)[33]
      • Substituted phenethylamines are dangerous to combine with MAOIs.
    • 2C-T-7 (suspected, strong)[33]
      • Substituted phenethylamines are dangerous to combine with MAOIs.
    • Bromo-DragonFLY (suspected, very strong)[34]
      • Dangerous to combine with MAOIs.
  • Pharmaceuticals
    • Bifemelane (Alnert, Celeport) (available in Japan)
    • Isocarboxazid (common brand name Marplan)
    • Methylthioninium chloride (Urelene blue, Provayblue, Proveblue), commonly called methylene blue. — Pure methylene blue is frequently sold as a dying agent and thus easy to obtain.
    • Phenelzine (common brand name Nardil)
    • Pirlindole (Pirazidol) (available in Russia)
    • Tranylcypromine (common brand name Parnate)

Selective MAO-B inhibitors

  • Naturally occurring sources
    • Kava (Piper methysticum): Yangonin. Kava pyrones: The order of potency was desmethoxyyangonin > (+/-)-methysticin > yangonin > (+/-)-dihydromethysticin > (+/-)- dihydrokavain > (+/-)-kavain.[35]
    • Olives (Olea europaea), fresh, olive leaf extract: The selective MAO-B inhibitor hydroxytyrosol.[36]
  • Pharmaceuticals
    • Rasagiline (Azilect)
    • Selegiline (Deprenyl, Eldepryl, Emsam, Zelapar)
    • Safinamide (Xadago)

Unknown selectivity

Toxicity and harm potential

Commons-emblem-notice.svg There are no antidotes for MAOI toxicity.[37] Also, too many psychoactive substances interact with MAOI and even RIMAs, so it's not even possible to list all the drug families that interact with them. Independent research should always be done to ensure that a combination of two or more substances is safe before consumption.

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

Warning: Many psychoactive substances that are reasonably safe to use on their own can suddenly become dangerous and even life-threatening when combined with certain other substances. The following list provides some known dangerous interactions (although it is not guaranteed to include all of them).

Always conduct independent research (e.g. Google, DuckDuckGo, PubMed) to ensure that a combination of two or more substances is safe to consume. Some of the listed interactions have been sourced from TripSit.

  • 2C-T-x - MAO-B inhibitors can increase the potency and duration of phenethylamines unpredictably, which could be dangerous given the unpredictability of the 2C-T-x series
  • 2C-x - MAO-B inhibitors can increase the potency and duration of phenethylamines unpredictably
  • DOx - MAO-B inhibitors can increase the potency and duration of phenethylamines unpredictably
  • Ketamine - MAO-B inhibitors appear to increase the potency of Ketamine. MAO-A inhbitors have some negative reports associated with the combination but there isn't much information available
  • Mescaline
  • NBOMes - MAO-B inhibitors can increase the potency and duration of phenethylamines unpredictably
  • Opioids - Coadministration of monoamine oxidase inhibitors (MAOIs) with certain opioids has been associated with rare reports of severe and fatal adverse reactions. There appear to be two types of interaction, an excitatory and a depressive one. Symptoms of the excitatory reaction may include agitation, headache, diaphoresis, hyperpyrexia, flushing, shivering, myoclonus, rigidity, tremor, diarrhea, hypertension, tachycardia, seizures, and coma. Death has occurred in some cases.
  • Alcohol - Tyramine found in many alcoholic beverages can have dangerous reactions with MAOIs, causing an increase in blood pressure.
  • MXE - MAO-B inhibitors appear to increase the potency of MXE. MAO-A inhbitors have some negative reports associated with the combination but there isn't much information available
  • 5-MeO-xxT
  • Amphetamines - MAO-B inhibitors can increase the potency and duration of phenethylamines unpredictably. MAO-A inhibitors with amphetamine can lead to hypertensive crises.
  • aMT - aMT is an MAOI on its own. Using enzyme inhibitors can greatly reduce predictability of effects.
  • Cocaine - This combination is poorly explored
  • DXM - High risk of serotonin syndrome
  • MDMA - MAO-B inhibitors can increase the potency and duration of phenethylamines unpredictably. MAO-A inhibitors with MDMA will lead to hypertensive crises.
  • PCP - This combination is very poorly explored
  • SSRIs
  • Tramadol

Psychoactive naturally occurring sources with high tyramine content

Specie Tyramine (mg/gram of alive plant)[40]
L. williamsii 0.5 - 1
L. jourdaniana 0.6
L. diffusa 0.1
L. fricii 0.1
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

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.[60]
  • Antihistamines (allergy medicines used to treat allergic conjunctivitis most often caused by hay fever), for example desloratadine, and loratadine. MAOI safe alternative: Cromoglicic acid eye drops.
  • Antitussives
    • Cold medicine
  • Decongestants
  • 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.[61][62] 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).[63] However, eating foods rich in tyramine while taking high doses of MAO-B inhibitors can cause a sudden increase in blood pressure.[64]

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.[65] Tyramine rich food should also be avoided by people prone to headache and migraine.

Tyramine rich foods

Specific foods with high amounts of tyramine:[66][67][68]

  • Aged cheese (gouda, camembert, cheddar) -- Few cheeses (even. 'mature' cheeses) contain more than 25 mg of tyramine in 100 grams.[69] However, Stilton (a blue cheese) contains up to 217 mg tyramine per 100 grams.[66]
  • 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
    • Chocolate milk
    • Chocolate, especially dark chocolate
    • Dried and/or candied fruit rolled in cocoa powder
  • Licorice (isoliquiritigenin and liquiritigenin are non-selective MAOIs).[20]
    • 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.[67] 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.[70]

Research

  • Naturally occurring sources
    • Mimosa tenuiflora: As there have been no MAO inhibitors detected in M. tenuiflora, there is ongoing interest into how yurema exerts its visionary effects.[71]

See also

External links

References

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  2. ↑ Nardil (Phenelzine Sulfate) - The BEST Antidepressant For Social Anxiety & Depression, 2020 
  3. ↑ Li, L., Galloway, G. P., Verotta, D., Everhart, E. T., Baggott, M. J., Coyle, J. R., Lopez, J. C., Mendelson, J. (July 2011). "A Method to Quantify Illicit Intake of Drugs from Urine: Methamphetamine". The Journal of Pharmacology and Experimental Therapeutics. 338 (1): 31–36. doi:10.1124/jpet.111.179176. ISSN 0022-3565. 
  4. ↑ Ellis, G. M., Mann, M. A., Judson, B. A., Schramm, N. T., Tashchian, A. (November 1985). "Excretion patterns of cannabinoid metabolites after last use in a group of chronic users". Clinical Pharmacology and Therapeutics. 38 (5): 572–578. doi:10.1038/clpt.1985.226. ISSN 0009-9236. 
  5. ↑ Janicak, P. G., Marder, S. R., Pavuluri, M. N. (26 December 2011). Principles and Practice of Psychopharmacotherapy. Lippincott Williams & Wilkins. ISBN 9781451178777. 
  6. ↑ Roberts AJ; Heyser CJ; Cole M; Griffin P; Koob GF (June 2000). "Excessive ethanol drinking following a history of dependence: animal model of allostasis". Neuropsychopharmacology. 22 (6): 581–94. doi:10.1016/S0893-133X(99)00167-0. PMID 10788758. 
  7. ↑ De Soto CB, O'Donnell WE, De Soto JL (October 1989). "Long-term recovery in alcoholics". Alcohol Clin Exp Res. 13 (5): 693–7. doi:10.1111/j.1530-0277.1989.tb00406.x. PMID 2688470. 
  8. ↑ 8.0 8.1 8.2 8.3 Banisteriopsis Caapi - an overview, ScienceDirect Topics 
  9. ↑ Jiao, Ye; Yan, Yan; He, Zhiyong; Gao, Daming; Qin, Fang; Lu, Mei; Xie, Mingyong; Chen, Jie; Zeng, Maomao (2018-06-20). "Inhibitory effects of catechins on β-carbolines in tea leaves and chemical model systems". Food & Function. 9 (6): 3126–3133. doi:10.1039/c7fo02053h. ISSN 2042-650X. PMID 29789822. 
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  13. ↑ 13.0 13.1 13.2 13.3 Cite error: Invalid <ref> tag; no text was provided for refs named Berlin2001
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  16. ↑ 16.0 16.1 Gottumukkala, R. V. S. S., Nadimpalli, N., Sukala, K., Subbaraju, G. V. (28 October 2014). "Determination of Catechin and Epicatechin Content in Chocolates by High-Performance Liquid Chromatography". International Scholarly Research Notices. 2014: 628196. doi:10.1155/2014/628196. ISSN 2356-7872. 
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  19. ↑ 19.0 19.1 Herraiz, T; Chaparro, C (14 January 2005). "Human monoamine oxidase is inhibited by tobacco smoke: beta-carboline alkaloids act as potent and reversible inhibitors". Biochemical and biophysical research communications. 326 (2): 378–86. doi:10.1016/j.bbrc.2004.11.033. PMID 15582589. 
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  33. ↑ 33.0 33.1 http://www.bluelight.org/vb/threads/385484-2C-T-family-and-MAOI-properties
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  39. ↑ Crosby, D.M.; McLaughlin, J.L. (Dec 1973). "Cactus Alkaloids. XIX Crystallization of Mescaline HCl and 3-Methoxytyramine HCl from Trichocereus panchanoi" (PDF). Lloydia and the Journal of Natural Products. 36 (4): 416–418. PMID 4773270. Retrieved 13 December 2013. 
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  45. ↑ Erowid Morning Glory Vault: Basics 
  46. ↑ 46.0 46.1 Tayebati, S. K., Tomassoni, D., Nwankwo, I. E., Di Stefano, A., Sozio, P., Cerasa, L. S., Amenta, F. (1 February 2013). "Modulation of monoaminergic transporters by choline-containing phospholipids in rat brain". CNS & neurological disorders drug targets. 12 (1): 94–103. doi:10.2174/1871527311312010015. ISSN 1996-3181. 
  47. ↑ Trabucchi, M., Govoni, S., Battaini, F. (April 1986). "Changes in the interaction between CNS cholinergic and dopaminergic neurons induced by L-alpha-glycerylphosphorylcholine, a cholinomimetic drug". Il Farmaco; Edizione Scientifica. 41 (4): 325–334. ISSN 0430-0920. 
  48. ↑ 48.0 48.1 48.2 Stancheva, S. L., Alova, L. G. (June 1988). "[Effect of centrophenoxine, piracetam and aniracetam on the monoamine oxidase activity in different brain structures of rats]". Farmakologiia I Toksikologiia. 51 (3): 16–18. ISSN 0014-8318. 
  49. ↑ Secades, J. J., Lorenzo, J. L. (September 2006). "Citicoline: pharmacological and clinical review, 2006 update". Methods and Findings in Experimental and Clinical Pharmacology. 28 Suppl B: 1–56. ISSN 0379-0355. 
  50. ↑ https://www.sps.nhs.uk/articles/what-is-the-risk-of-interaction-between-opioids-and-monoamine-oxidase-inhibitors-maois/
  51. ↑ Russo EB, Burnett A, Hall B, Parker KK (August 2005). "Agonistic properties of cannabidiol at 5-HT1a receptors". Neurochemical Research. 30 (8): 1037–43. doi:10.1007/s11064-005-6978-1. PMID 16258853. 
  52. ↑ Seeman, P., Guan, H.-C., Hirbec, H. (August 2009). "Dopamine D2 High receptors stimulated by phencyclidines, lysergic acid diethylamide, salvinorin A, and modafinil". Synapse. 63 (8): 698–704. doi:10.1002/syn.20647. ISSN 0887-4476. 
  53. ↑ Seeman, P. (October 2016). "Cannabidiol is a partial agonist at dopamine D2High receptors, predicting its antipsychotic clinical dose". Translational Psychiatry. 6 (10): e920. doi:10.1038/tp.2016.195. ISSN 2158-3188. 
  54. ↑ Erowid 5-MeO-AMT Vault: Basics 
  55. ↑ 55.0 55.1 55.2 Nagai, F., Nonaka, R., Satoh Hisashi Kamimura, K. (22 March 2007). "The effects of non-medically used psychoactive drugs on monoamine neurotransmission in rat brain". European Journal of Pharmacology. 559 (2–3): 132–137. doi:10.1016/j.ejphar.2006.11.075. ISSN 0014-2999. 
  56. ↑ Erowid 5-MeO-DMT Vault : Health 
  57. ↑ Erowid 5-MeO-MIPT Vault: Basics 
  58. ↑ Erowid Datura Vaults : Datura FAQ 
  59. ↑ https://www.jwatch.org/fw108796/2014/05/06/severe-hypertension-linked-caffeine-mao-inhibitor
  60. ↑ "Transderm Scop patch prescribing information". Archived from the original on 4 February 2009. 
  61. ↑ https://www.ajol.info/index.php/jomip/article/view/213795
  62. ↑ https://pubmed.ncbi.nlm.nih.gov/31736764/
  63. ↑ https://pubmed.ncbi.nlm.nih.gov/10063483/
  64. ↑ https://www.parkinsons.org.uk/information-and-support/mao-b-inhibitors-rasagiline-selegiline-safinamide
  65. ↑ Sathyanarayana Rao, T. S., Yeragani, V. K. (2009). "Hypertensive crisis and cheese". Indian Journal of Psychiatry. 51 (1): 65–66. doi:10.4103/0019-5545.44910. ISSN 0019-5545. 
  66. ↑ 66.0 66.1 https://www.mc.vanderbilt.edu/documents/neurology/files/Tyramine%20Menu%20Book%2006227101.pdf
  67. ↑ 67.0 67.1 Paulsen, P., Grossgut, R., Bauer, F., Rauscher-Gabernig, E. (2012). "Estimates of maximum tolerable levels of tyramine content in foods in Austria". Journal of Food and Nutrition Research (Slovak Republic). 
  68. ↑ McCabe-Sellers, B. J., Staggs, C. G., Bogle, M. L. (August 2006). "Tyramine in foods and monoamine oxidase inhibitor drugs: A crossroad where medicine, nutrition, pharmacy, and food industry converge". Journal of Food Composition and Analysis. 19: S58–S65. doi:10.1016/j.jfca.2005.12.008. ISSN 0889-1575. 
  69. ↑ https://psychotropical.info/wp-content/uploads/2018/02/MAOI_diet_drug_interactions_2017.pdf
  70. ↑ Erowid LSD (Acid) Vault : LSD and Antidepressants, by Mike 
  71. ↑ Dimethyltryptamine - an overview, ScienceDirect Topics 
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