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Harmine information


Harmine
Names
Preferred IUPAC name
7-Methoxy-1-methyl-9H-pyrido[3,4-b]indole
Identifiers
CAS Number
  • 442-51-3 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:28121 checkY
ChEMBL
  • ChEMBL269538 checkY
ChemSpider
  • 4444445 checkY
DrugBank
  • DB07919 checkY
ECHA InfoCard 100.006.485 Edit this at Wikidata
KEGG
  • C06538 checkY
PubChem CID
  • 5280953
UNII
  • 4FHH5G48T7 checkY
CompTox Dashboard (EPA)
  • DTXSID30196066 Edit this at Wikidata
InChI
  • InChI=1S/C13H12N2O/c1-8-13-11(5-6-14-8)10-4-3-9(16-2)7-12(10)15-13/h3-7,15H,1-2H3 checkY
    Key: BXNJHAXVSOCGBA-UHFFFAOYSA-N checkY
  • InChI=1/C13H12N2O/c1-8-13-11(5-6-14-8)10-4-3-9(16-2)7-12(10)15-13/h3-7,15H,1-2H3
    Key: BXNJHAXVSOCGBA-UHFFFAOYAR
SMILES
  • COc1ccc2c(c1)[nH]c3c(C)nccc23
Properties
Chemical formula
C13H12N2O
Molar mass 212.25 g/mol
Density 1.326 g/cm3
Melting point 321 °C (610 °F; 594 K) (·HCl); 262 °C (·HCl·2H2O)[2]
Solubility in water
insoluble[1]
Solubility in Dimethyl sulfoxide 100mM[1]
Solubility in Ethanol 1 mg/mL[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
Infobox references

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.[3] 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.[4] Harmine is also known as banisterin, banisterine, telopathin, telepathine, leucoharmine[5] and yagin, yageine.[3][6]

  1. ^ a b c "Harmine - CAS 442-51-3". scbio.de. Santa Cruz Biotechnology, Inc. Retrieved 27 October 2015.
  2. ^ The Merck Index (1996). 12th edition
  3. ^ a b Djamshidian A, et al. (2015). "Banisteriopsis caapi, a Forgotten Potential Therapy for Parkinson's Disease?". Movement Disorders Clinical Practice. 3 (1): 19–26. doi:10.1002/mdc3.12242. PMC 6353393. PMID 30713897.
  4. ^ Frecska E, Bokor P, Winkelman M (2016). "The Therapeutic Potentials of Ayahuasca: Possible Effects against Various Diseases of Civilization". Frontiers in Pharmacology. 7: 35. doi:10.3389/fphar.2016.00035. PMC 4773875. PMID 26973523.
  5. ^ Allen JR, Holmstedt BR (1980). "The simple β-carboline alkaloids". Phytochemistry. 19 (8): 1573–1582. Bibcode:1980PChem..19.1573A. doi:10.1016/S0031-9422(00)83773-5.
  6. ^ "SciFinderⁿ Login". sso.cas.org. Retrieved 2021-11-12.

and 28 Related for: Harmine information

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Harmine

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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...

Word Count : 2016

Harmala alkaloid

Last Update:

(Ayahuasca), leaves of tobacco and coffee beans. The alkaloids include harmine, harmaline, harmalol, and their derivatives, which have similar chemical...

Word Count : 1526

Peganum harmala

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contained in the plant, including the seeds, are monoamine oxidase inhibitors (Harmine, Harmaline). African rue is often used in North American English. Harmel...

Word Count : 7139

List of psychoactive plants

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Beta-carbolines Banisteriopsis lutea, Harmine, telepathine Banisteriopsis metallicolor, Harmine, telepathine Banisteriopsis muricata Harmine up to 6%, harmaline up to...

Word Count : 7618

Harmaline

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harmala alkaloids and beta-carbolines. It is the partly hydrogenated form of harmine. Various plants contain harmaline including Peganum harmala (Syrian rue)...

Word Count : 875

Pharmahuasca

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uses a pharmaceutical MAOI instead of a plant. N,N-DMT and harmaline or harmine are typically used as components of pharmahuasca.[citation needed] As a...

Word Count : 310

Ayahuasca

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paraphernalia with traces of harmine and DMT, discovered in a cave in southwestern Bolivia in 2008. and chemical traces of harmine in the hair of two mummies...

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Banisteriopsis caapi

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support.[unreliable source?] Caapi contains the following harmala alkaloids: Harmine, 0.31–8.43% Harmaline, 0.03–0.83% Tetrahydroharmine, 0.05–2.94% These alkaloids...

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Indole alkaloid

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include harmine, harmaline, harmane and a slightly more complex structure of canthinone. Harmaline was first isolated in 1838 by Göbel and harmine in 1848...

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Passiflora caerulea

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Passiflora incarnata, this plant contains higher amounts of the MAO-inhibitor harmine. Though the fruit is edible, it is rather insipid when eaten raw. A tea...

Word Count : 943

Oxalis

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tuber root caps are covered in a fluorescent slush rich in harmaline and harmine which apparently suppresses pests. Creeping wood sorrel and perhaps other...

Word Count : 1800

Tetrahydroharmine

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caapi. THH, like other harmala alkaloids in B. caapi, namely harmaline and harmine, is a reversible inhibitor of monoamine oxidase A (RIMA), but it also inhibits...

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Oxidase test

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Journal of General Microbiology. 25, 297–306. Zanderigo F et al. 2018. [11C]Harmine Binding to Brain Monoamine Oxidase A: Test-Retest Properties and Noninvasive...

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Psychonautics

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visually seen by the listener. (See: synesthesia) The ayahuasca ingredient, harmine, was once known as telepathine because of this group-facilitated activity...

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Psilocybin mushroom

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occur in different genera, such as Psilocybe,Cyclocybe, and Hygrophorus. Harmine, harmane, norharmane and a range of other l-tryptophan-derived β-carbolines...

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Standard for the Uniform Scheduling of Medicines and Poisons

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Cannabis, except when separately specified in other Schedules Coca leaf DMT Harmine/Harmaline Heroin Kratom, also known as Mitragyna speciosa; as well its...

Word Count : 1906

Elaeagnus angustifolia

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eaten during Nowruz in Afghanistan. E. angustifolia contains the alkaloids harmine, harmane, and harmol in the roots and shoot, as well as calligonine in...

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Harmol

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β-carboline. It is readily formed in vivo in humans by O-demethylation of harmine. Harmalol Abe A, Kokuba H (2013). "Harmol induces autophagy and subsequent...

Word Count : 211

Harmane

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also present in tobacco smoke. Harmane is related to other alkaloids, harmine and harmaline, found in 1837 in the plant Peganum harmala. The name derives...

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Nicotiana tabacum

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leaves and stems which includes harmala alkaloids as well. Yohimbine, harmine, harmaline and ajmalicine occurs in descending order, yohimbine being highest...

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Tobacco

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inhibits dopamine metabolism from its MAOI activity. Tobacco also contains Harmine and Norharmine which is a reversible MAO-A inhibitor. The MAO-A activity...

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Mimosa tenuiflora

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Jonathan Ott (1998). "Pharmahuasca: Human pharmacology of oral DMT plus Harmine". Journal of Psychoactive Drugs. 31 (2): 171–7. doi:10.1080/02791072.1999...

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Brunfelsia pauciflora

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particular they contain indole alkaloids derived from Beta-carboline such as harmine, tetrahydroharmine, harmaline, manacin, manacein, and dimethyltryptamine...

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Dopaminergic

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selegiline, rasagiline, and pargyline, as well as the harmala alkaloids like harmine, harmaline, tetrahydroharmine, harmalol, harman, and norharman, which are...

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Monoamine oxidase inhibitor

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(Cantor) Pirlindole (Pirazidol) Naturally occurring RIMAs in plants Harmaline Harmine Rosiridin (in vitro) Research compounds Amiflamine (FLA-336) Befloxatone...

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Passiflora

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The most common of these alkaloids is harman, but harmaline, harmalol, harmine, and harmol are also present. The species known to bear such alkaloids...

Word Count : 3675

Alkaloid

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dimethyltryptamine (DMT), bufotenin Simple derivatives of β-carboline Harman, harmine, harmaline, eleagnine Pyrroloindole alkaloids Physostigmine (eserine),...

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Terence McKenna

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experiment in which the brothers attempted to "bond harmine DNA with their own neural DNA" (harmine is another psychedelic compound they used synergistically...

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