Harmaline
Encyclopedia
Harmaline is a fluorescent psychoactive indole
alkaloid
from the group of harmala alkaloids and beta-carboline
s. It is the reduced hydrogenated form of harmine
.
(a jungle vine) and Peganum harmala (Syrian Rue) as well as the hallucinogenic drink ayahuasca
, which is traditionally brewed using Banisteriopsis caapi. Also passionflower (Passiflora incarnata) and tobacco.
Harmaline is a central nervous system
stimulant
and a "reversible inhibitor
of MAO
-A (RIMA
)." It being a reversible MAO-A inhibitor means that it competes with tyramine
for binding to MAO-A, so foods containing some tyramine
can be safely consumed (wine and aged cheese should probably be avoided for 12 hours prior to consuming harmaline containing plants). The reversibility means that, instead of binding permanently to MAO-A for weeks until the body replaces the MAO-A enzyme molecules, harmaline binds only transiently, so tyramine can be metabolized as well by competing with harmaline for the binding site on the enzyme. This means that the risk of a hypertensive crisis, a dangerous high blood pressure crisis from eating tyramine
-rich foods such as cheese, is potentially lower with harmaline than with non-reversible MAOIs such as Nardil, especially after 24 hours following ingestion.
Harmaline is shown to act as an acetylcholinesterase
inhibitor. Harmaline also stimulates striatal
dopamine release in rat at very high dose levels.
Depending upon the dosage, harmaline induces temporary oneirophrenia
and ataxia
. Harmaline, on the higher end of its safe dosage range, has hallucinogenic properties, but it differentiates itself significantly from the "classical" hallucinogens in its pharmacology
. Since harmaline is a reversible monoamine oxidase inhibitor
, it could increase the effect of some drugs problematically. Harmaline causes no known physical or psychological dependence.
United States Patent
Number 5591738 describes a method for treating various chemical dependencies via the administration of harmaline and or other beta-carbolines.
Claudio Naranjo
has studied potential applications of harmal alkaloids in psychotherapy
.
Harmaline has also been shown to induce "vasorelaxant effects" in "isolated rat aorta
."
Harmaline has both protective and toxic effects on neuron
s.
Harmaline is known to act as a histamine N-methyltransferase
inhibitor.
Indole
Indole is an aromatic heterocyclic organic compound. It has a bicyclic structure, consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring. Indole is a popular component of fragrances and the precursor to many pharmaceuticals. Compounds that contain an...
alkaloid
Alkaloid
Alkaloids are a group of naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic properties. Also some synthetic compounds of similar structure are attributed to alkaloids...
from the group of harmala alkaloids and beta-carboline
Beta-carboline
β-Carboline is an organic amine that is the prototype of a class of compounds known as β-carbolines.-Pharmacology:...
s. It is the reduced hydrogenated form of harmine
Harmine
Harmine is a fluorescent harmala alkaloid belonging to the beta-carboline family of compounds. It occurs in a number of different plants, most notably the Middle Eastern plant harmal or Syrian rue and the South American vine Banisteriopsis caapi...
.
Occurrence in nature
Various plants contain harmaline including Banisteriopsis caapiBanisteriopsis caapi
Banisteriopsis caapi, also known as Ayahuasca, Caapi or Yage, is a South American jungle vine of the family Malpighiaceae. It is used to prepare Ayahuasca, a decoction that has a long history of entheogenic uses as a medicine and "plant teacher" among the indigenous peoples of the Amazon Rainforest...
(a jungle vine) and Peganum harmala (Syrian Rue) as well as the hallucinogenic drink ayahuasca
Ayahuasca
Ayahuasca is any of various psychoactive infusions or decoctions prepared from the Banisteriopsis spp. vine, usually mixed with the leaves of dimethyltryptamine-containing species of shrubs from the Psychotria genus...
, which is traditionally brewed using Banisteriopsis caapi. Also passionflower (Passiflora incarnata) and tobacco.
Effects
Central nervous system
The central nervous system is the part of the nervous system that integrates the information that it receives from, and coordinates the activity of, all parts of the bodies of bilaterian animals—that is, all multicellular animals except sponges and radially symmetric animals such as jellyfish...
stimulant
Stimulant
Stimulants are psychoactive drugs which induce temporary improvements in either mental or physical function or both. Examples of these kinds of effects may include enhanced alertness, wakefulness, and locomotion, among others...
and a "reversible inhibitor
Monoamine oxidase inhibitor
Monoamine oxidase inhibitors are a class of antidepressant drugs prescribed for the treatment of depression. They are particularly effective in treating atypical depression....
of MAO
Monoamine oxidase
L-Monoamine oxidases are a family of enzymes that catalyze the oxidation of monoamines. They are found bound to the outer membrane of mitochondria in most cell types in the body. The enzyme was originally discovered by Mary Bernheim in the liver and was named tyramine oxidase...
-A (RIMA
Rima
Rima, also known as Rima the Jungle Girl, is the fictional heroine of W. H. Hudson's 1904 novel Green Mansions: A Romance of the Tropical Forest. In 1974, she was adapted into a comic book character and featured in the short-lived monthly series Rima the Jungle Girl, published by DC Comics...
)." It being a reversible MAO-A inhibitor means that it competes with tyramine
Tyramine
Tyramine is a naturally occurring monoamine compound and trace amine derived from the amino acid tyrosine. Tyramine acts as a catecholamine releasing agent...
for binding to MAO-A, so foods containing some tyramine
Tyramine
Tyramine is a naturally occurring monoamine compound and trace amine derived from the amino acid tyrosine. Tyramine acts as a catecholamine releasing agent...
can be safely consumed (wine and aged cheese should probably be avoided for 12 hours prior to consuming harmaline containing plants). The reversibility means that, instead of binding permanently to MAO-A for weeks until the body replaces the MAO-A enzyme molecules, harmaline binds only transiently, so tyramine can be metabolized as well by competing with harmaline for the binding site on the enzyme. This means that the risk of a hypertensive crisis, a dangerous high blood pressure crisis from eating tyramine
Tyramine
Tyramine is a naturally occurring monoamine compound and trace amine derived from the amino acid tyrosine. Tyramine acts as a catecholamine releasing agent...
-rich foods such as cheese, is potentially lower with harmaline than with non-reversible MAOIs such as Nardil, especially after 24 hours following ingestion.
Harmaline is shown to act as an acetylcholinesterase
Acetylcholinesterase
"Acetylcholinesterase, also known as AChE or acetylcholine acetylhydrolase, is an enzyme that degrades the neurotransmitter acetylcholine, producing choline and an acetate group. It is mainly found at neuromuscular junctions and cholinergic nervous system, where its activity serves to terminate...
inhibitor. Harmaline also stimulates striatal
Striatum
The striatum, also known as the neostriatum or striate nucleus, is a subcortical part of the forebrain. It is the major input station of the basal ganglia system. The striatum, in turn, gets input from the cerebral cortex...
dopamine release in rat at very high dose levels.
Depending upon the dosage, harmaline induces temporary oneirophrenia
Oneirophrenia
Oneirophrenia is a hallucinatory, dream-like state caused by several conditions such as prolonged sleep deprivation, sensory deprivation, or drugs . From the Greek words "ὄνειρο" and "φρενός"...
and ataxia
Ataxia
Ataxia is a neurological sign and symptom that consists of gross lack of coordination of muscle movements. Ataxia is a non-specific clinical manifestation implying dysfunction of the parts of the nervous system that coordinate movement, such as the cerebellum...
. Harmaline, on the higher end of its safe dosage range, has hallucinogenic properties, but it differentiates itself significantly from the "classical" hallucinogens in its pharmacology
Pharmacology
Pharmacology is the branch of medicine and biology concerned with the study of drug action. More specifically, it is the study of the interactions that occur between a living organism and chemicals that affect normal or abnormal biochemical function...
. Since harmaline is a reversible monoamine oxidase inhibitor
Monoamine oxidase inhibitor
Monoamine oxidase inhibitors are a class of antidepressant drugs prescribed for the treatment of depression. They are particularly effective in treating atypical depression....
, it could increase the effect of some drugs problematically. Harmaline causes no known physical or psychological dependence.
United States Patent
Patent
A patent is a form of intellectual property. It consists of a set of exclusive rights granted by a sovereign state to an inventor or their assignee for a limited period of time in exchange for the public disclosure of an invention....
Number 5591738 describes a method for treating various chemical dependencies via the administration of harmaline and or other beta-carbolines.
Claudio Naranjo
Claudio Naranjo
Claudio Naranjo is a Chilean psychiatrist who is considered a pioneer in integrating psychotherapy and the spiritual traditions. He is one of the three successors named by Fritz Perls , and a developer of the Enneagram of Personality and founder of the Seekers After Truth Institute...
has studied potential applications of harmal alkaloids in psychotherapy
Psychotherapy
Psychotherapy is a general term referring to any form of therapeutic interaction or treatment contracted between a trained professional and a client or patient; family, couple or group...
.
Harmaline has also been shown to induce "vasorelaxant effects" in "isolated rat aorta
Aorta
The aorta is the largest artery in the body, originating from the left ventricle of the heart and extending down to the abdomen, where it branches off into two smaller arteries...
."
Harmaline has both protective and toxic effects on neuron
Neuron
A neuron is an electrically excitable cell that processes and transmits information by electrical and chemical signaling. Chemical signaling occurs via synapses, specialized connections with other cells. Neurons connect to each other to form networks. Neurons are the core components of the nervous...
s.
Harmaline is known to act as a histamine N-methyltransferase
Histamine N-methyltransferase
Histamine N-methyltransferase is one of two enzymes involved in the metabolism of histamine. The other being diamine oxidase. Histamine N-methyltransferase catalyzes the methylation of histamine in the presence of S-adenosylmethionine forming N-methylhistamine. HMT is present in most body tissues...
inhibitor.