Harmane Guide: Effects, Benefits, Risks, and Legality

• What Is Harmane?
• Natural Sources of Harmane
• Harmane Chemical Structure and Active Mechanisms
• Harmane Experience
• Harmane Benefits
• Harmane Risks
• Harmane in Psilocybin Mushroom Dosing
• Harmane Legality
• Bottom Line

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Harmane is a naturally occurring psychoactive alkaloid (chemical) found in various plant and animal sources, including ayahuasca and certain magic mushrooms. It is known for its unique physiological effects on the human body, including mild hallucinogenic properties and potential neuroprotective effects. Harmane’s presence in magic mushrooms has been of particular interest to researchers due to its potential contribution to the psychedelic experience.

This guide details harmane’s most common natural sources, chemical structure, benefits and risks, and legality. 

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What Is Harmane?

Harmane (harman) is a chemical compound in the family of beta-carboline alkaloids. It is found in various foods, including cheese, meat, and beer. It has also been found in plant sources such as Banisteriopsis caapi, the main ingredient in ayahuasca, and several species of psychedelic mushrooms.

Human tissues and body fluids also contain certain β-carbolines, such as harmane. Research demonstrates these alkaloids display diverse biological activities. For instance, beta carbolines can act as scavengers against reactive oxygen species, giving harmane antioxidant effects. Harmane also shows neuroprotective, antidepressant, and anti-HIV properties, with therapeutic potential in treating Alzheimer’s, Parkinson’s, and depression.

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Natural Harmane Containing Foods and Other Sources

Harmane exists in high concentrations in foods and substances common in many diets, including:

• Coffee
• Barbecued and grilled meats (hamburgers, chicken, and beef)
• Vinegar
• Soy sauce
• Cheese
• Tobacco (cigarette smoke) 
• Alcoholic beverages

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Harmane also occurs in mammalian tissues and body fluids, including the

• Central nervous system
• Heart
• Kidney
• Liver
• Adrenal tissue
• Platelets
• Plasma
• Urine

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Various plants & fungi known for hallucinogenic properties also contain harmane, such as 

• Peganum harmala (wild rue)
• Banisteriopsis caapi (the ayahuasca brew vine)
• Tribulus terrestris (bindii)
• Psilocybin-containing mushrooms (like conocybe, galerina, gymnopilus, inocybe, panaeolus, pholiotina, pluteus, psilocybe)

In a recent study, scientists discovered the psychedelic mushroom species, P. Mexicana, and P. cubensis, contain harmane and other beta-carbolines, like harmine. 

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What is the Structure of Harmane?

Harmane (1-methyl-9H-pyrido-indole) is a chemical compound with a specific structure that influences its effects on the brain. Harmane's structure includes three connected rings, known as a "tricyclic" structure, which is common among certain natural chemicals called alkaloids. These tricyclic structures make harmane part of the beta-carboline family of alkaloids.

Harmane has a particular arrangement where a methyl group (a small chemical group made of one carbon and three hydrogen atoms) is attached at a specific point on one of these rings.

Harmane also belongs to a broader category called "indole alkaloids," which are compounds that share a structural similarity with serotonin, a crucial neurotransmitter in the brain. This similarity means that harmane can influence brain function in ways comparable to serotonin, affecting mood, cognition, and other neurological processes.

Harmane's chemical structure explains why it can have significant effects on neural activity and behavior.

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How Does Harmane Function in the Body?

Highly lipophilic

Harmane can dissolve in fats, making it more easily distributed into brain tissues. Harmane concentration in the brain can be more than 55 times higher than in plasma. 

Monoamine oxidase inhibitor (MAOI)

Harmane is a potent inhibitor of monoamine oxidase, an enzyme that breaks down neurotransmitters like serotonin, dopamine, and norepinephrine. MAOIs increase happy-hormone levels by inhibiting this enzyme, making them effective antidepressants.

Neural Protection

‍Harmane has been shown to act on various receptor systems in the brain, such as serotonin, opiate, dopamine, imidazoline, and benzodiazepines. Furthermore, harmane exerts strong inhibition against acetylcholinesterase and butyrylcholinesterase, enzymes found in brain cells primarily at postsynaptic neuromuscular junctions. Therefore, harmane can potentially support Alzheimer’s, Parkinson’s, and depression treatments.

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Harmane Experience

Harmane can reportedly exert locomotor and psychoactive effects through its physiological mechanisms and neurotransmitter action. 

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Visual effects:

• Pattern recognition enhancement
• Tracers
• Vibrating vision
• Color enhancement

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Cognitive effects:

• Dream potentiation
• Time distortion
• Creativity
• Conceptual thinking
• Anxiety
• Confusion

Harmane Benefits

Harmane primarily influences brain function and exhibits antioxidant effects. 

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Antioxidant properties

‍Indoles like harmane exhibit antioxidant actions by scavenging free radicals and creating more balance in the body. Free radicals are responsible for oxidative stress, which can damage cells and lead to age-related and chronic diseases. In a 3D model study, increased harmane concentrations reduced oxidative stress levels. 

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Neuroprotective properties

‍Studies show harmane alkaloids protect neurons from damage through their antioxidant properties. Additionally, as an MAOI, harmane can increase the levels of important neurotransmitters in the brain, which may help to protect neurons from damage and reduce the risk of neurodegenerative diseases.

The harmane-β-carboline alkaloid has shown several pharmacological activities and success over the years, making it the foundation of numerous clinically used drugs. In particular, harmane exerts potential in therapies for: 

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• Diabetes
• Neurodegenerative and cardiovascular diseases
• Inflammation
• Alzheimer’s and Parkinson's diseases
• Depression
• Modulating neuronal responses to stress

• Inhibiting HIV replication

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Harmane Risks

Harmane is a neuroprotective agent at low to moderate doses. However, it’s also neurotoxic in large amounts. 

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‍Tremor-inducing

‍Although harmane shows promise as a treatment for Parkinson’s and nerve-related diseases, some research shows blood harmane levels can be abnormally increased in essential tremor (ET) patients. This fact also incriminates harmane in the pathogenesis of ET, a symptom of Parkinson’s disease. 

‍Learning and memory

Pre-clinical studies also observed adverse effects on learning and memory at relatively high doses. In a rat study, harmane significantly impaired working memory, which involves holding information over short periods, at doses of 5 mg/kg and 7.5 mg/kg. Additionally, at the highest dose of 7.5 mg/kg, harmane significantly increased the time (latency) it took for the rats to complete the tasks compared to the control group.

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Harmane in Psilocybin Mushroom Dosing 

Harmane can be toxic in large amounts. However, harmine is barely traceable in mushroom species compared to their main psychedelic substance, psilocybin. 

The presence of harmane and other beta-carboline compounds is so low, it’s unlikely they affect the mushroom experience significantly. However, some researchers speculate thatsome kind of entourage effect could occur via the interaction of beta-carboline alkaloids and other psychedelic substances in magic mushrooms. 

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Harmane Legality

Harmane and other harmala alkaloids and their natural sources are legal in most parts of the world. In the United States, the Controlled Substances Act and the Drug Enforcement Agency (DEA) do not specifically mention these substances, making them federally permissible. 

The US Department of Agriculture (USDA) regulates some sources of harmane, such as Peganum harmala (Syrian rue). In September 2019, the USDA openly restricted Peganum harmala in Arizona, California, Colorado, Nevada, New Mexico, and Oregon, which regulates the plant to prevent it from becoming an invasive species.

Some countries, including Australia, Canada, and France, list harmala alkaloids like harmane and harmine as illegal drugs or limit their preparations. 

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Bottom Line

Harmane is one of several beta-carboline alkaloids recently isolated from psilocybin mushrooms. Harmane also exists naturally in plants, body tissues, and many common foods, including coffee, cooked meats, and tobacco. Like other beta-carboline alkaloids, harmane displays antioxidant, anti-inflammatory, and neuroprotective properties. It has significant potential in treating various diseases, including Alzheimer’s, Parkinson's, depression, and HIV. However, harmane also possesses tremor-inducing qualities, requiring further study. 

With magic mushroom use increasing in popularity, mycological enthusiasts, medicinal patients, and DEA-licensed clients want to be better informed about mushroom products and their active ingredients. ACS Laboratory has cutting-edge techniques and equipment to ensure the potency and purity of multiple psychedelic compounds, including harmala alkaloids such as harmane. Contact ACS Laboratory about quality mushroom testing.