Names | |
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Preferred IUPAC name 1-Methyl-9H-pyrido[3,4-b]indole | |
Other names Harman, Aribine, Aribin, Locuturine, Locuturin, Loturine, Passiflorin, 1-Methylnorharman, NSC 54439 | |
Identifiers | |
3D model (JSmol) | |
ChEBI | |
ChemSpider | |
ECHA InfoCard | 100.006.948 |
EC Number |
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KEGG | |
PubChem CID | |
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CompTox Dashboard (EPA) | |
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Properties | |
C12H10N2 | |
Molar mass | 182.226 g·mol−1 |
Melting point | 235–238 °C (455–460 °F; 508–511 K) |
Soluble to 10 mM in 1 eq. HCl methanol: soluble 50 mg/ml | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Harmane (harman) is a heterocyclic amine found in a variety of foods including coffee, [1] sauces, [2] and cooked meat. [3] It is also present in tobacco smoke. [4]
Harmane is related to other alkaloids, harmine and harmaline, found in 1837 in the plant Peganum harmala . [5] The name derives from the Arabic word for the plant, حَرْمَل (ḥarmal).
In humans, harmane is a potent tremor-producing neurotoxin. [6] Harmane has been found to inhibit the early stages of the growth of the malaria parasite in the gut of mosquitoes infected by the bacterium Delftia tsuruhatensis , and can be absorbed by the mosquitoes upon contact. [7] [8] [9]
Harmane is a methylated derivative of β-carboline with the molecular formula C12H10N2.
Family | Plant |
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Rubiaceae | Coffea arabica [1] |
Solanaceae | Nicotiana tabacum [10] |
Theaceae | Camellia sinensis [11] |
In 1962, Poindexter et al. found that there was very little harmane in tobacco, but a significant amount in tobacco smoke. They showed that it is produced from tryptophan by the heat of burning the tobacco. [10]
Banisteriopsis caapi, also known as, caapi, soul vine, yagé (yage), or ayahuasca, the latter of which also refers to the psychedelic decoction made with the vine and a plant source of dimethyltryptamine, is a South American liana of the family Malpighiaceae. It is commonly used as an ingredient of ayahuasca, a decoction with a long history of its entheogenic use and holds status as a "plant teacher" among the Indigenous peoples of the Amazon rainforest.
β-Carboline (9H-pyrido[3,4-b]indole) represents the basic chemical structure for more than one hundred alkaloids and synthetic compounds. The effects of these substances depend on their respective substituent. Natural β-carbolines primarily influence brain functions but can also exhibit antioxidant effects. Synthetically designed β-carboline derivatives have recently been shown to have neuroprotective, cognitive enhancing and anti-cancer properties.
Harmala alkaloids are several alkaloids that act as monoamine oxidase inhibitors (MAOIs). These alkaloids are found in the seeds of Peganum harmala, as well as Banisteriopsis caapi (ayahuasca), leaves of tobacco and coffee beans. The alkaloids include harmine, harmaline, harmalol, and their derivatives, which have similar chemical structures, hence the name "harmala alkaloids". These alkaloids are of interest for their use in Amazonian shamanism, where they are derived from other plants. Harmine, once known as telepathine and banisterine, is a naturally occurring beta-carboline alkaloid that is structurally related to harmaline, and also found in the vine Banisteriopsis caapi. Tetrahydroharmine is also found in B. caapi and P. harmala. Dr. Alexander Shulgin has suggested that harmine may be a breakdown product of harmaline. Harmine and harmaline are reversible inhibitors of monoamine oxidase A (RIMAs). They can stimulate the central nervous system by inhibiting the metabolism of monoamine compounds such as serotonin and norepinephrine.
Peganum harmala, commonly called wild rue, Syrian rue, African rue, esfand or espand, or harmel, is a perennial, herbaceous plant, with a woody underground rootstock, of the family Nitrariaceae, usually growing in saline soils in temperate desert and Mediterranean regions. Its common English-language name came about because of a resemblance to rue. Because eating it would sicken or kill livestock, it is considered a noxious weed in a number of countries. It has become an invasive species in some regions of the western United States. The plant is popular in Middle Eastern and north African folk medicine. The alkaloids contained in the plant, including the seeds, are monoamine oxidase inhibitors.
Harmine is a beta-carboline and a harmala alkaloid. It occurs in a number of different plants, most notably the Syrian rue and Banisteriopsis caapi. Harmine reversibly inhibits monoamine oxidase A (MAO-A), an enzyme which breaks down monoamines, making it a Reversible inhibitor of monoamine oxidase A (RIMA). Harmine does not inhibit MAO-B. Harmine is also known as banisterin, banisterine, telopathin, telepathine, leucoharmine and yagin, yageine.
Harmaline is a fluorescent indole alkaloid from the group of harmala alkaloids and beta-carbolines. It is the partly hydrogenated form of harmine.
Tetrahydroharmine (THH) is a fluorescent indole alkaloid that occurs in the tropical liana species Banisteriopsis caapi.
Pharmahuasca is a pharmaceutical version of the entheogenic brew ayahuasca. Traditional ayahuasca is made by brewing the MAOI-containing Banisteriopsis caapi vine with a DMT-containing plant, such as Psychotria viridis. Pharmahuasca refers to a similar combination that uses a pharmaceutical MAOI instead of a plant.
Dopaminergic means "related to dopamine", a common neurotransmitter. Dopaminergic substances or actions increase dopamine-related activity in the brain.
Tetrahydroharmol is a bioactive beta-carboline harmala alkaloid. It acts as a reversible inhibitor of monoamine oxidase A.
Indole alkaloids are a class of alkaloids containing a structural moiety of indole; many indole alkaloids also include isoprene groups and are thus called terpene indole or secologanin tryptamine alkaloids. Containing more than 4100 known different compounds, it is one of the largest classes of alkaloids. Many of them possess significant physiological activity and some of them are used in medicine. The amino acid tryptophan is the biochemical precursor of indole alkaloids.
Heterocyclic amines, also sometimes referred to as HCAs, are chemical compounds containing at least one heterocyclic ring, which by definition has atoms of at least two different elements, as well as at least one amine (nitrogen-containing) group. Typically it is a nitrogen atom of an amine group that also makes the ring heterocyclic, though compounds exist in which this is not the case. The biological functions of heterocyclic amines vary, including vitamins and carcinogens. Carcinogenic heterocyclic amines are created by high temperature cooking of meat and smoking of plant matter like tobacco. Some well known heterocyclic amines are niacin, nicotine, and the nucleobases that encode genetic information in DNA.
Tryptoline, also known as tetrahydro-β-carboline and tetrahydronorharmane, is a natural organic derivative of beta-carboline. It is an alkaloid chemically related to tryptamines. Derivatives of tryptoline have a variety of pharmacological properties and are known collectively as tryptolines.
Tetrahydroharman(e), also known as 1-methyl-1,2,3,4-tetrahydro-β-carboline, is a general name for one of two isomers:
Pinoline is a methoxylated tryptoline (5-methoxytryptoline) long claimed to be produced in the pineal gland during the metabolism of melatonin, however its pineal occurrence remains controversial. Its IUPAC name is 6-methoxy-1,2,3,4-tetrahydro-β-carboline, usually abbreviated as 6-MeO-THBC, and its more common name is a combination of "pineal beta-carboline". The biological activity of this molecule is of interest as a potential free radical scavenger, also known as an antioxidant, and as a monoamine oxidase A inhibitor.
Delftia tsuruhatensis is a Gram-negative, rod-shaped, catalase- and oxidase-positive, motile bacterium from the Comamonadaceae family. It was first isolated from a wastewater treatment plant in Japan in 2003. D. tsuruhatensis is an opportunistic and emergent pathogen. All documented human infections are healthcare-associated.
Peganum nigellastrum is a plant species in the genus Peganum. "Peganum nigellastrum is distributed in China and east Siberia. This species has also been recorded in the subprovinces of Mongolia and Tsinhai" and is found in the Hami region, a prefecture-level city, of Xinjiang Uygur Autonomous Region, China.
9-Methyl-β-carboline (9-Me-BC) is a heterocyclic amine of the β-carboline family, and a research chemical.