Overview
Harmala alkaloids are a family of beta-carboline compounds found naturally in several plant species, most notably Peganum harmala (Syrian rue) andBanisteriopsis caapi (the ayahuasca vine). The principal alkaloids in this family areharmine,harmaline, andtetrahydroharmine (THH), all of which share a tricyclic indole structure built on a pyrido[3,4-b]indole scaffold .
These compounds are best known for their role as reversible inhibitors of monoamine oxidase A (rMAO-A), an enzyme responsible for the degradation of serotonin, norepinephrine, and dopamine. This MAO-inhibiting property is the pharmacological key to ayahuasca: by blocking intestinal and hepatic MAO-A, harmala alkaloids prevent the first-pass metabolism of DMT, allowing it to reach the brain intact after oral ingestion. Without the harmala component, orally consumed DMT would be rapidly degraded and remain psychoactively inert .
Beyond their role in ayahuasca pharmacology, harmala alkaloids have attracted research attention for their neuroprotective,anti-inflammatory, andantioxidant properties. Harmine in particular has shown cognition-enhancing effects in animal models, mediated in part through increased BDNF (brain-derived neurotrophic factor) expression and reduced neuroinflammation. The beta-carbolines also display notablefluorescence properties due to their extended aromatic ring system, making them useful as analytical markers .
Syrian rue seeds accumulate harmine and harmaline at concentrations of approximately 4.3% and 5.6% by dry weight respectively, making them one of the most concentrated natural sources of beta-carboline alkaloids .
References
- Herraiz T, et al. Beta-carboline alkaloids in Peganum harmala and inhibition of human monoamine oxidase (MAO). Food Chem Toxicol. 2010;48(3):839-845.
- Moloudizargari M, et al. Pharmacological and therapeutic effects of Peganum harmala and its main alkaloids. Pharmacogn Rev. 2013;7(14):199-212.
- McKenna DJ. Clinical investigations of the therapeutic potential of ayahuasca. Pharmacol Ther. 2004;102(2):111-129.
- Dos Santos RG, Hallak JEC. Effects of the natural beta-carboline alkaloid harmine, a main constituent of ayahuasca, in memory and in the hippocampus. Front Pharmacol. 2017;8:862.
Safety at a Glance
High Risk- It is strongly recommended that one use harm reduction practices when using this drug.
- There is no tolerance built up with harmala alkaloid use. There are no real reports of addiction to harmala alkaloids.
- Toxicity: - Drug interactions MAOIs have highly dangerous and sometimes fatal interactions with many common drugs. They can cau...
- Dangerous with: 1,4-Butanediol, 2-Aminoindane, 2-FA, 2-FEA (+123 more)
- Overdose risk: fatal interactions with many common drugs. They can cause serotonin syndrome or hypertensive cris...
If someone is in crisis, call 911 or Poison Control: 1-800-222-1222
Duration
No duration data available.
Subjective Effects
The effects listed below are based on the Subjective Effect Index (SEI), an open research literature based on anecdotal reports and personal analyses. They should be viewed with a healthy degree of skepticism. These effects will not necessarily occur in a predictable or reliable manner, although higher doses are more liable to induce the full spectrum of effects.
Physical Effects
Physical(5)
- Diarrhea— Diarrhea is the occurrence of frequent, loose, or watery bowel movements as a side effect of certain...
- Headache— A painful sensation of pressure, throbbing, or aching in the head that can range from a dull backgro...
- Sedation— A state of deep physical and mental calming that manifests as a progressive desire to remain still, ...
- Serotonin syndrome— Serotonin syndrome is a potentially fatal medical emergency caused by excessive serotonergic activit...
- Stimulation— A state of heightened physical and mental energy characterized by increased wakefulness, elevated mo...
Cognitive & Perceptual Effects
Cognitive(2)
- Anxiety— Intense feelings of apprehension, worry, and dread that can range from a subtle background unease to...
- Cognitive dysphoria— A cognitive and emotional state of intense dissatisfaction, discomfort, and malaise encompassing fee...
Pharmacology
Pharmacology
Monoamine Oxidase Inhibition
The defining pharmacological property of harmala alkaloids is their potent, reversible, and competitive inhibition of monoamine oxidase A (MAO-A). Herraiz et al. (2010) demonstrated that seed extracts of Peganum harmala inhibit human MAO-A with an IC50 of just 27 microg/L, an effect quantitatively attributable to their harmaline and harmine content. Critically, these alkaloids show no significant activity against MAO-B, making them highly selective reversible MAO-A inhibitors (RIMAs) .
This selectivity has profound pharmacological consequences. By inhibiting MAO-A in the gut wall and liver, harmala alkaloids prevent the first-pass degradation of orally ingested tryptamines — most famously DMT in the ayahuasca preparation. The reversible nature of the inhibition (in contrast to irreversible MAOIs like phenelzine) means that the enzyme's function recovers within hours, reducing the risk of prolonged hypertensive crises .
Beyond MAO Inhibition
Harmala alkaloids interact with a remarkably broad range of neuronal targets beyond MAO-A. Published receptor profiling data show activity at opioid, dopamine, GABA, 5-HT (serotonin), benzodiazepine, and imidazoline receptors . Harmine produces dose-dependent augmentation of dopamine efflux and modulates levels of serotonin and dopamine metabolites — effects attributable to both MAO-A inhibition and direct receptor interactions .
Neuroprotective Properties
A growing body of evidence supports neuroprotective effects for several harmala alkaloids:
- Harmine improves memory and learning in multiple animal models and increases brain-derived neurotrophic factor (BDNF) levels while reducing neurotoxicity, inflammation, and oxidative stress
- Harmaline and harmine both inhibit acetylcholinesterase (AChE), myeloperoxidase (MPO), and demonstrate significant antioxidant and anti-inflammatory activity
- Banisteriopsis caapi alkaloids have been proposed as potential therapeutic agents for Parkinson's disease, based on their combined MAO-inhibitory and neuroprotective profiles
Fluorescent Properties
The extended aromatic beta-carboline ring system gives harmala alkaloids distinctive fluorescence characteristics. Harmaline and harmine emit strongly overlapping fluorescence spectra in the 300-400 nm range upon excitation at 285 nm, with pH-dependent spectral shifts. These properties enable spectrofluorometric quantification methods and have been exploited for analytical detection in biological matrices .
References
- Herraiz T, et al. Beta-carboline alkaloids in Peganum harmala and inhibition of human monoamine oxidase (MAO). Food Chem Toxicol. 2010;48(3):839-845.
- Moloudizargari M, et al. Pharmacological and therapeutic effects of Peganum harmala and its main alkaloids. Pharmacogn Rev. 2013;7(14):199-212.
- Riba J, et al. Human pharmacology of ayahuasca: subjective and cardiovascular effects, monoamine metabolite excretion, and pharmacokinetics. J Pharmacol Exp Ther. 2003;306(1):73-83.
- Dos Santos RG, Hallak JEC. Effects of the natural beta-carboline alkaloid harmine, a main constituent of ayahuasca, in memory and in the hippocampus. Front Pharmacol. 2017;8:862.
- Biradar SM, et al. Analogous beta-carboline alkaloids harmaline and harmine ameliorate scopolamine-induced cognition dysfunction. Front Pharmacol. 2018;9:346.
- Djamshidian A, Poewe W. Banisteriopsis caapi, a forgotten potential therapy for Parkinson's disease? Mov Disord Clin Pract. 2016;3(1):19-26.
- Salim AA, et al. Innovative spectrofluorometric method for determination of harmaline and harmine in different matrices. Sci Rep. 2023;13:19247.
Interactions
| Substance | Status | Note |
|---|---|---|
| 1,4-Butanediol | Dangerous | Unpredictable potentiation of CNS depression; risk of respiratory failure |
| 2-Aminoindane | Dangerous | Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination |
| 2-FA | Dangerous | Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination |
| 2-FEA | Dangerous | Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination |
| 2-FMA | Dangerous | Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination |
| 2,5-DMA | Dangerous | Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination |
| 2C-H | Dangerous | Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination |
| 2M2B | Dangerous | Unpredictable potentiation of CNS depression; risk of respiratory failure |
| 3-FA | Dangerous | Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination |
| 3-FEA | Dangerous | Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination |
| 3-FMA | Dangerous | Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination |
| 3-FPM | Dangerous | Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination |
| 3-MMC | Dangerous | Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination |
| 3,4-CTMP | Dangerous | Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination |
| 4-FA | Dangerous | Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination |
| 4-FMA | Dangerous | Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination |
| 4-MMC | Dangerous | Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination |
| 4F-EPH | Dangerous | Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination |
| 4F-MPH | Dangerous | Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination |
| 5-APB | Dangerous | Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination |
| 5-MAPB | Dangerous | Extreme serotonin syndrome risk; potentially fatal — MAOIs massively potentiate MDMA |
| 5-MeO-MiPT | Dangerous | Extreme serotonin syndrome risk; potentially fatal — MAOIs massively potentiate MDMA |
| 6-APB | Dangerous | Extreme serotonin syndrome risk; potentially fatal — MAOIs massively potentiate MDMA |
| 6-APDB | Dangerous | Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination |
| 8-Chlorotheophylline | Dangerous | Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination |
| A-PHP | Dangerous | Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination |
| A-PVP | Dangerous | Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination |
| Acetylfentanyl | Dangerous | Risk of serotonin syndrome and severe respiratory depression; potentially fatal |
| Adrafinil | Dangerous | Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination |
| Alcohol | Dangerous | Unpredictable potentiation of CNS depression; risk of respiratory failure |
| Alprazolam | Dangerous | Unpredictable potentiation of CNS depression; risk of respiratory failure |
| Amphetamine | Dangerous | Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination |
| Armodafinil | Dangerous | Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination |
| Baclofen | Dangerous | Unpredictable potentiation of CNS depression; risk of respiratory failure |
| Benzodiazepines | Dangerous | Unpredictable potentiation of CNS depression; risk of respiratory failure |
| Benzydamine | Dangerous | Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination |
| Bromantane | Dangerous | Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination |
| Buprenorphine | Dangerous | Risk of serotonin syndrome and severe respiratory depression; potentially fatal |
| Butylone | Dangerous | Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination |
| Caffeine | Dangerous | Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination |
| Cake | Dangerous | Unpredictable potentiation of CNS depression; risk of respiratory failure |
| Carisoprodol | Dangerous | Unpredictable potentiation of CNS depression; risk of respiratory failure |
| Clonazepam | Dangerous | Unpredictable potentiation of CNS depression; risk of respiratory failure |
| Clonazolam | Dangerous | Unpredictable potentiation of CNS depression; risk of respiratory failure |
| Clonidine | Dangerous | Unpredictable potentiation of CNS depression; risk of respiratory failure |
| Cocaine | Dangerous | Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination |
| Codeine | Dangerous | Risk of serotonin syndrome and severe respiratory depression; potentially fatal |
| Cyclazodone | Dangerous | Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination |
| Deschloroetizolam | Dangerous | Unpredictable potentiation of CNS depression; risk of respiratory failure |
| Desomorphine | Dangerous | Risk of serotonin syndrome and severe respiratory depression; potentially fatal |
| Desoxypipradrol | Dangerous | Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination |
| Dextroamphetamine | Dangerous | Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination |
| Dextropropoxyphene | Dangerous | Risk of serotonin syndrome and severe respiratory depression; potentially fatal |
| Diazepam | Dangerous | Unpredictable potentiation of CNS depression; risk of respiratory failure |
| Dichloropane | Dangerous | Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination |
| Diclazepam | Dangerous | Unpredictable potentiation of CNS depression; risk of respiratory failure |
| Dihydrocodeine | Dangerous | Risk of serotonin syndrome and severe respiratory depression; potentially fatal |
| Ephedrine | Dangerous | Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination |
| Ephylone | Dangerous | Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination |
| Eszopiclone | Dangerous | Unpredictable potentiation of CNS depression; risk of respiratory failure |
| ETH-CAT | Dangerous | Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination |
| Ethylmorphine | Dangerous | Risk of serotonin syndrome and severe respiratory depression; potentially fatal |
| Ethylone | Dangerous | Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination |
| Ethylphenidate | Dangerous | Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination |
| Etizolam | Dangerous | Unpredictable potentiation of CNS depression; risk of respiratory failure |
| F-Phenibut | Dangerous | Unpredictable potentiation of CNS depression; risk of respiratory failure |
| Fenethylline | Dangerous | Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination |
| Fentanyl | Dangerous | Risk of serotonin syndrome and severe respiratory depression; potentially fatal |
| Flualprazolam | Dangerous | Unpredictable potentiation of CNS depression; risk of respiratory failure |
| Flubromazepam | Dangerous | Unpredictable potentiation of CNS depression; risk of respiratory failure |
| Flubromazolam | Dangerous | Unpredictable potentiation of CNS depression; risk of respiratory failure |
| Flunitrazepam | Dangerous | Unpredictable potentiation of CNS depression; risk of respiratory failure |
| Flunitrazolam | Dangerous | Unpredictable potentiation of CNS depression; risk of respiratory failure |
| Gabapentin | Dangerous | Unpredictable potentiation of CNS depression; risk of respiratory failure |
| Gaboxadol | Dangerous | Unpredictable potentiation of CNS depression; risk of respiratory failure |
| GBL | Dangerous | Unpredictable potentiation of CNS depression; risk of respiratory failure |
| GHB | Dangerous | Unpredictable potentiation of CNS depression; risk of respiratory failure |
| Grayanotoxin | Dangerous | Unpredictable potentiation of CNS depression; risk of respiratory failure |
| Heroin | Dangerous | Risk of serotonin syndrome and severe respiratory depression; potentially fatal |
| Hexedrone | Dangerous | Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination |
| Hydrocodone | Dangerous | Risk of serotonin syndrome and severe respiratory depression; potentially fatal |
| Hydromorphone | Dangerous | Risk of serotonin syndrome and severe respiratory depression; potentially fatal |
| Isopropylphenidate | Dangerous | Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination |
| Kratom | Dangerous | Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination |
| Lisdexamfetamine | Dangerous | Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination |
| Lorazepam | Dangerous | Unpredictable potentiation of CNS depression; risk of respiratory failure |
| MCPP | Dangerous | Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination |
| MDA | Dangerous | Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination |
| MDAI | Dangerous | Extreme serotonin syndrome risk; potentially fatal — MAOIs massively potentiate MDMA |
| MDEA | Dangerous | Extreme serotonin syndrome risk; potentially fatal — MAOIs massively potentiate MDMA |
| MDMA | Dangerous | Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination |
| MDPV | Dangerous | Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination |
| Mephenaqualone | Dangerous | Unpredictable potentiation of CNS depression; risk of respiratory failure |
| Methadone | Dangerous | Risk of serotonin syndrome and severe respiratory depression; potentially fatal |
| Methamphetamine | Dangerous | Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination |
| Methaqualone | Dangerous | Unpredictable potentiation of CNS depression; risk of respiratory failure |
| Methcathinone | Dangerous | Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination |
| Methiopropamine | Dangerous | Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination |
| Methylnaphthidate | Dangerous | Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination |
| Methylone | Dangerous | Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination |
| Methylphenidate | Dangerous | Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination |
| Metizolam | Dangerous | Unpredictable potentiation of CNS depression; risk of respiratory failure |
| Mexedrone | Dangerous | Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination |
| Midazolam | Dangerous | Unpredictable potentiation of CNS depression; risk of respiratory failure |
| Mirtazapine | Dangerous | Unpredictable potentiation of CNS depression; risk of respiratory failure |
| Modafinil | Dangerous | Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination |
| Morphine | Dangerous | Risk of serotonin syndrome and severe respiratory depression; potentially fatal |
| N-Ethylhexedrone | Dangerous | Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination |
| N-Methylbisfluoromodafinil | Dangerous | Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination |
| Naloxone | Dangerous | Risk of serotonin syndrome and severe respiratory depression; potentially fatal |
| NEP | Dangerous | Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination |
| Nicotine | Dangerous | Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination |
| Nifoxipam | Dangerous | Unpredictable potentiation of CNS depression; risk of respiratory failure |
| NM-2-AI | Dangerous | Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination |
| O-Desmethyltramadol | Dangerous | Risk of serotonin syndrome and severe respiratory depression; potentially fatal |
| Oxiracetam | Dangerous | Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination |
| Oxycodone | Dangerous | Risk of serotonin syndrome and severe respiratory depression; potentially fatal |
| Oxymorphone | Dangerous | Risk of serotonin syndrome and severe respiratory depression; potentially fatal |
| Pentedrone | Dangerous | Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination |
| Pentobarbital | Dangerous | Unpredictable potentiation of CNS depression; risk of respiratory failure |
| Pethidine | Dangerous | Risk of serotonin syndrome and severe respiratory depression; potentially fatal |
| Phenobarbital | Dangerous | Unpredictable potentiation of CNS depression; risk of respiratory failure |
| Phenylpiracetam | Dangerous | Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination |
| PMA | Dangerous | Extreme serotonin syndrome risk; potentially fatal — MAOIs massively potentiate MDMA |
| PMMA | Dangerous | Extreme serotonin syndrome risk; potentially fatal — MAOIs massively potentiate MDMA |
| Rhodiola Rosea | Dangerous | Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination |
| SAMe | Dangerous | Unpredictable potentiation of CNS depression; risk of respiratory failure |
| 1,3-Butanediol | Caution | MAOIs dramatically potentiate psychedelics; drastically reduce dose and exercise extreme caution |
| 1B-LSD | Caution | MAOIs dramatically potentiate psychedelics; drastically reduce dose and exercise extreme caution |
| 1cP-AL-LAD | Caution | MAOIs dramatically potentiate psychedelics; drastically reduce dose and exercise extreme caution |
| 1cP-LSD | Caution | MAOIs dramatically potentiate psychedelics; drastically reduce dose and exercise extreme caution |
| 1cP-MiPLA | Caution | MAOIs dramatically potentiate psychedelics; drastically reduce dose and exercise extreme caution |
History
History
Ancient and Traditional Use
Peganum harmala (Syrian rue) has been used ritually and medicinally since antiquity. The Greek-Roman physician Galen mentioned the plant in the second century AD, and its seeds have been burned as incense throughout the Near East and North Africa for centuries — a practice that continues to this day. In traditional Iranian and Central Asian folk medicine, Syrian rue preparations were used as emmenagogues, antihelminthics, and treatments for various ailments .
On the other side of the world, indigenous Amazonian peoples developed ayahuasca — a decoction combining Banisteriopsis caapi (which contains harmine, harmaline, and THH) with DMT-containing plants such as Psychotria viridis. The pharmacological sophistication of this preparation is remarkable: the beta-carboline MAO inhibitors in the vine are precisely what is needed to render orally ingested DMT bioavailable .
Chemical Isolation
The isolation of harmala alkaloids began in the 19th century. German chemist H. Gobel isolated harmaline from Syrian rue seeds in 1841, and J. Fritsch isolated harmine from the same source in 1847. Fischer characterized harmalol from P. harmala in 1901. Independently, in 1923, Colombian chemist Guillermo Fischer Cardenas isolated the active alkaloid from B. caapi — and by 1925, collaborative work with Hoffmann-La Roche confirmed that "telepathine" and "yageine" (names given to the ayahuasca vine alkaloid by different researchers) were both identical to harmine .
Modern Research
Contemporary research has focused on the neuroprotective and therapeutic potential of harmala alkaloids, with studies exploring applications in depression, neurodegenerative diseases, and cognitive enhancement .
References
- Moloudizargari M, et al. Pharmacological and therapeutic effects of Peganum harmala and its main alkaloids. Pharmacogn Rev. 2013;7(14):199-212.
- McKenna DJ. Clinical investigations of the therapeutic potential of ayahuasca. Pharmacol Ther. 2004;102(2):111-129.
- Kahpi Ayahuasca Timeline. "Ayahuasca alkaloids were found in Syrian rue plant in 1841."
- Djamshidian A, Poewe W. Banisteriopsis caapi, a forgotten potential therapy for Parkinson's disease? Mov Disord Clin Pract. 2016;3(1):19-26.
- Dos Santos RG, Hallak JEC. Effects of the natural beta-carboline alkaloid harmine. Front Pharmacol. 2017;8:862.
Harm Reduction
It is strongly recommended that one use harm reduction practices when using this drug.
There is no tolerance built up with harmala alkaloid use. There are no real reports of addiction to harmala alkaloids.
Harmala alkaloids and their natural sources are legal in most parts of the world.
Australia:** Harmala alkaloids are Schedule 9 drugs under POISONS STANDARD of DECEMBER 2019. HARMALA ALKALOIDS except in herbs, or preparations, for therapeutic use:
containing 0.1 per cent or less of harmala alkaloids; or
in divided preparations containing 2 mg or less of harmala alkaloids per recommended daily dose.
Canada:** Harmala alkaloids are Schedule III drugs.
France:** Possession and sale of harmala alkaloids is illegal.
Responsible use
Beta-Carbolines
Psychedelics
Tryptamines
Phenethylamines
Harmala alkaloids
Harmala alkaloids (Wikipedia)
Harmaline (Wikipedia)
Harmine (Wikipedia)
Tetrahydroharmine (Wikipedia)
Harmala Alkaloids (Erowid Vault)
Harmaline (TiHKAL / Isomer Design)
Harmine (TiHKAL / Isomer Design)
Tetrahydroharmine (TiHKAL / Isomer Design)
Natural sources
Banisteriopsis caapi* (Wikipedia)
Banisteriopsis caapi* (Erowid Vault)
Peganum harmala* (Wikipedia)
Syrian rue (Erowid Vault)
Morales-García, J. A., de la Fuente Revenga, M., Alonso-Gil, S., Rodríguez-Franco, M. I., Feilding, A., Perez-Castillo, A., & Riba, J. (2017). The alkaloids of Banisteriopsis caapi, the plant source of the Amazonian hallucinogen Ayahuasca, stimulate adult neurogenesis in vitro. Scientific Reports, 7(1), 5309. https://doi.org/10.1038/s41598-017-05407-9
Toxicity & Safety
- Drug interactions
MAOIs have highly dangerous and sometimes fatal interactions with many common drugs. They can cause serotonin syndrome or hypertensive crisis when combined with almost any antidepressant, stimulant, common migraine medication, certain herbs, most cold medicine (including decongestants, antihistamines, and cough syrup), nicotine, caffeine, etc. Sedatives are likely easier tolerated, but potentiation should be expected.
- Cholinergics
Acetylcholinesterase inhibitors (AChEIs) combined with cholinergic substances can result in a cholinergic crisis.
Banisteriopsis caapi and Peganum harmala contain harmaline and harmine. Both alkaloids are acetylcholinesterase inhibitors (AChEIs).
When intravenously injected into mice, the LD50 of harmine is 38mg/kg. There is no data for the other harmala alkaloids in humans or animals.
It is strongly recommended that one use harm reduction practices when using this drug.
There is no tolerance built up with harmala alkaloid use. There are no real reports of addiction to harmala alkaloids.
Harmala alkaloids and their natural sources are legal in most parts of the world.
Australia:** Harmala alkaloids are Schedule 9 drugs under POISONS STANDARD of DECEMBER 2019. HARMALA ALKALOIDS except in herbs, or preparations, for therapeutic use:
containing 0.1 per cent or less of harmala alkaloids; or
in divided preparations containing 2 mg or less of harmala alkaloids per recommended daily dose.
Canada:** Harmala alkaloids are Schedule III drugs.
France:** Possession and sale of harmala alkaloids is illegal.
Responsible use
Beta-Carbolines
Psychedelics
Tryptamines
Phenethylamines
Harmala alkaloids
Harmala alkaloids (Wikipedia)
Harmaline (Wikipedia)
Harmine (Wikipedia)
Tetrahydroharmine (Wikipedia)
Harmala Alkaloids (Erowid Vault)
Harmaline (TiHKAL / Isomer Design)
Harmine (TiHKAL / Isomer Design)
Tetrahydroharmine (TiHKAL / Isomer Design)
Natural sources
Banisteriopsis caapi* (Wikipedia)
Banisteriopsis caapi* (Erowid Vault)
Peganum harmala* (Wikipedia)
Syrian rue (Erowid Vault)
Morales-García, J. A., de la Fuente Revenga, M., Alonso-Gil, S., Rodríguez-Franco, M. I., Feilding, A., Perez-Castillo, A., & Riba, J. (2017). The alkaloids of Banisteriopsis caapi, the plant source of the Amazonian hallucinogen Ayahuasca, stimulate adult neurogenesis in vitro. Scientific Reports, 7(1), 5309. https://doi.org/10.1038/s41598-017-05407-9
Overdose Information
fatal interactions with many common drugs. They can cause serotonin syndrome or hypertensive crisis when combined with almost any antidepressant, stimulant, common migraine medication, certain herbs, most cold medicine (including decongestants, antihistamines, and cough syrup), nicotine, caffeine, etc. Sedatives are likely easier tolerated, but potentiation should be expected.
- Cholinergics
Acetylcholinesterase inhibitors (AChEIs) combined with cholinergic substances can result in a cholinergic crisis.
Banisteriopsis caapi and Peganum harmala contain harmaline and harmine. Both alkaloids are acetylcholinesterase inhibitors (AChEIs).
When intravenously injected into mice, the LD50 of harmine is 38mg/kg. There is no data for the other harmala alkaloids in humans or animals.
It is strongly recommended that one use harm reduction practices when using this drug.
There is no tolerance built up with harmala alkaloid use. There are no real reports of addiction to harmala alkaloids.
Harmala alkaloids and their natural sources are legal in most parts of the world.
Australia:** Harmala alkaloids are Schedule 9 drugs under POISONS STANDARD of DECEMBER 2019. HARMALA ALKALOIDS except in herbs, or preparations, for therapeutic use:
containing 0.1 per cent or less of harmala alkaloids; or
in divided preparations containing 2 mg or less of harmala alkaloids per recommended daily dose.
Canada:** Harmala alkaloids are Schedule III drugs.
France:** Possession and sale of harmala alkaloids is illegal.
Responsible use
Beta-Carbolines
Psychedelics
Tryptamines
Phenethylamines
Harmala alkaloids
Harmala alkaloids (Wikipedia)
Harmaline (Wikipedia)
Harmine (Wikipedia)
Tetrahydroharmine (Wikipedia)
Harmala Alkaloids (Erowid Vault)
Harmaline (TiHKAL / Isomer Design)
Harmine (TiHKAL / Isomer Design)
Tetrahydroharmine (TiHKAL / Isomer Des
Dangerous Interactions
The combinations listed below may be life-threatening. Independent research should always be conducted to ensure safety when combining substances.
Unpredictable potentiation of CNS depression; risk of respiratory failure
Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination
Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination
Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination
Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination
Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination
Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination
Unpredictable potentiation of CNS depression; risk of respiratory failure
Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination
Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination
Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination
Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination
Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination
Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination
Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination
Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination
Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination
Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination
Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination
Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination
Extreme serotonin syndrome risk; potentially fatal — MAOIs massively potentiate MDMA
Extreme serotonin syndrome risk; potentially fatal — MAOIs massively potentiate MDMA
Extreme serotonin syndrome risk; potentially fatal — MAOIs massively potentiate MDMA
Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination
Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination
Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination
Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination
Risk of serotonin syndrome and severe respiratory depression; potentially fatal
Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination
Unpredictable potentiation of CNS depression; risk of respiratory failure
Unpredictable potentiation of CNS depression; risk of respiratory failure
Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination
Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination
Unpredictable potentiation of CNS depression; risk of respiratory failure
Unpredictable potentiation of CNS depression; risk of respiratory failure
Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination
Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination
Risk of serotonin syndrome and severe respiratory depression; potentially fatal
Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination
Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination
Unpredictable potentiation of CNS depression; risk of respiratory failure
Unpredictable potentiation of CNS depression; risk of respiratory failure
Unpredictable potentiation of CNS depression; risk of respiratory failure
Unpredictable potentiation of CNS depression; risk of respiratory failure
Unpredictable potentiation of CNS depression; risk of respiratory failure
Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination
Risk of serotonin syndrome and severe respiratory depression; potentially fatal
Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination
Unpredictable potentiation of CNS depression; risk of respiratory failure
Risk of serotonin syndrome and severe respiratory depression; potentially fatal
Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination
Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination
Risk of serotonin syndrome and severe respiratory depression; potentially fatal
Unpredictable potentiation of CNS depression; risk of respiratory failure
Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination
Unpredictable potentiation of CNS depression; risk of respiratory failure
Risk of serotonin syndrome and severe respiratory depression; potentially fatal
Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination
Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination
Unpredictable potentiation of CNS depression; risk of respiratory failure
Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination
Risk of serotonin syndrome and severe respiratory depression; potentially fatal
Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination
Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination
Unpredictable potentiation of CNS depression; risk of respiratory failure
Unpredictable potentiation of CNS depression; risk of respiratory failure
Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination
Risk of serotonin syndrome and severe respiratory depression; potentially fatal
Unpredictable potentiation of CNS depression; risk of respiratory failure
Unpredictable potentiation of CNS depression; risk of respiratory failure
Unpredictable potentiation of CNS depression; risk of respiratory failure
Unpredictable potentiation of CNS depression; risk of respiratory failure
Unpredictable potentiation of CNS depression; risk of respiratory failure
Unpredictable potentiation of CNS depression; risk of respiratory failure
Unpredictable potentiation of CNS depression; risk of respiratory failure
Unpredictable potentiation of CNS depression; risk of respiratory failure
Unpredictable potentiation of CNS depression; risk of respiratory failure
Unpredictable potentiation of CNS depression; risk of respiratory failure
Risk of serotonin syndrome and severe respiratory depression; potentially fatal
Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination
Risk of serotonin syndrome and severe respiratory depression; potentially fatal
Risk of serotonin syndrome and severe respiratory depression; potentially fatal
Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination
Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination
Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination
Unpredictable potentiation of CNS depression; risk of respiratory failure
Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination
Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination
Extreme serotonin syndrome risk; potentially fatal — MAOIs massively potentiate MDMA
Extreme serotonin syndrome risk; potentially fatal — MAOIs massively potentiate MDMA
Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination
Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination
Unpredictable potentiation of CNS depression; risk of respiratory failure
Risk of serotonin syndrome and severe respiratory depression; potentially fatal
Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination
Unpredictable potentiation of CNS depression; risk of respiratory failure
Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination
Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination
Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination
Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination
Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination
Unpredictable potentiation of CNS depression; risk of respiratory failure
Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination
Unpredictable potentiation of CNS depression; risk of respiratory failure
Unpredictable potentiation of CNS depression; risk of respiratory failure
Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination
Risk of serotonin syndrome and severe respiratory depression; potentially fatal
Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination
Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination
Risk of serotonin syndrome and severe respiratory depression; potentially fatal
Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination
Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination
Unpredictable potentiation of CNS depression; risk of respiratory failure
Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination
Risk of serotonin syndrome and severe respiratory depression; potentially fatal
Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination
Risk of serotonin syndrome and severe respiratory depression; potentially fatal
Risk of serotonin syndrome and severe respiratory depression; potentially fatal
Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination
Unpredictable potentiation of CNS depression; risk of respiratory failure
Risk of serotonin syndrome and severe respiratory depression; potentially fatal
Unpredictable potentiation of CNS depression; risk of respiratory failure
Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination
Extreme serotonin syndrome risk; potentially fatal — MAOIs massively potentiate MDMA
Extreme serotonin syndrome risk; potentially fatal — MAOIs massively potentiate MDMA
Risk of hypertensive crisis and serotonin syndrome; potentially fatal combination
Unpredictable potentiation of CNS depression; risk of respiratory failure
Tolerance
| Full | Unknown |
| Half | Unknown |
| Zero | Unknown |
Legal Status
Harmala alkaloids and their natural sources are legal in most parts of the world.
Australia:** Harmala alkaloids are Schedule 9 drugs under POISONS STANDARD of DECEMBER 2019. HARMALA ALKALOIDS except in herbs, or preparations, for therapeutic use:
containing 0.1 per cent or less of harmala alkaloids; or
in divided preparations containing 2 mg or less of harmala alkaloids per recommended daily dose.
Canada:** Harmala alkaloids are Schedule III drugs.
France:** Possession and sale of harmala alkaloids is illegal.
Responsible use
Beta-Carbolines
Psychedelics
Tryptamines
Phenethylamines
Harmala alkaloids
Harmala alkaloids (Wikipedia)
Harmaline (Wikipedia)
Harmine (Wikipedia)
Tetrahydroharmine (Wikipedia)
Harmala Alkaloids (Erowid Vault)
Harmaline (TiHKAL / Isomer Design)
Harmine (TiHKAL / Isomer Design)
Tetrahydroharmine (TiHKAL / Isomer Design)
Natural sources
Banisteriopsis caapi* (Wikipedia)
Banisteriopsis caapi* (Erowid Vault)
Peganum harmala* (Wikipedia)
Syrian rue (Erowid Vault)
Morales-García, J. A., de la Fuente Revenga, M., Alonso-Gil, S., Rodríguez-Franco, M. I., Feilding, A., Perez-Castillo, A., & Riba, J. (2017). The alkaloids of Banisteriopsis caapi, the plant source of the Amazonian hallucinogen Ayahuasca, stimulate adult neurogenesis in vitro. Scientific Reports, 7(1), 5309. https://doi.org/10.1038/s41598-017-05407-9
Experience Reports (2)
Tips (3)
Always start with a low dose of Harmala alkaloid and work your way up. Individual sensitivity varies, and you cannot undo a dose once taken.
Research potential interactions before combining Harmala alkaloid with other substances. Drug interactions can be unpredictable and dangerous.
Keep a usage log for Harmala alkaloid including dose, time, effects, and side effects. This helps you identify patterns and prevent problematic escalation.
See Also
References (2)
- Harmala alkaloid - TripSit Factsheet
TripSit factsheet for Harmala alkaloid
tripsit - Harmala alkaloid - Wikipedia
Wikipedia article on Harmala alkaloid
wikipedia