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Chemical compound
Harmaline, also known as 7-methoxyharmalan or as 3,4-dihydro-7-methoxy-1-methyl-β-carboline, is a harmala alkaloid and β-carboline which has hallucinogenic
Harmaline
Drug that produces a dream-like state of consciousness
oneirophrenic, or oneiric, was introduced to refer specifically to ibogaine- and harmaline-type hallucinogens by William Turner and Claudio Naranjo in the 1960s
Oneirogen
Psychoactive substance found in plants in the family Apocynaceae
altered state of consciousness is shared with harmala alkaloids like harmaline but is distinct from that of other hallucinogens like serotonergic psychedelics
Ibogaine
Group of chemical compounds
(ayahuasca), leaves of tobacco and coffee beans. The alkaloids include harmine, harmaline, harmalol, and their derivatives, which have similar chemical structures
Harmala_alkaloid
Chemical compound
harmala alkaloids. Some β-carbolines, like harmaline, are hallucinogenic. According to Alexander Shulgin, harmaline is the only β-carboline that has been extensively
Substituted_β-carboline
Psychedelic drug
(MAOI) such as the reversible inhibitor of monoamine oxidase A (RIMA) harmaline to allow for oral activity and a much longer duration than it would have
5-MeO-DMT
Pharmaceutical compound
oxidase inhibitor, and hallucinogen of the β-carboline family related to harmaline (7-methoxyharmalan). It is a cyclized tryptamine and analogue of 5-MeO-DMT
6-Methoxyharmalan
South American psychoactive decoction
doses of ayahuasca or higher doses of isolated harmala alkaloids like harmaline may pose risks. There have been cases of death with dimethyltryptamine
Ayahuasca
Pharmaceutical compound
serotonergic psychedelics like LSD but similar to those of ibogaine. Along with harmaline and tetrahydroharmine, harmine is one of the psychoactive constituents
Harmine
Chemical compound
Banisteriopsis caapi. It is an oneirogenic hallucinogen similarly to harmaline. Conversely however, in contrast to other harmala alkaloids, it is very
Tetrahydroharmine
Psychedelic drug
inhibitor of MAO-A (RIMA) such as a harmala alkaloid like harmine or harmaline or a pharmaceutical RIMA like moclobemide, DMT becomes orally active with
Dimethyltryptamine
Class of indoles
complex compounds, for example cyclized tryptamines like LSD, ibogaine, harmaline, mitragynine and yohimbine. A thorough investigation of dozens of tryptamine
Substituted_tryptamine
Plant species in the family
possession of the seeds, the plant itself, and the alkaloids harmine and harmaline, which it contains, is illegal in France. In Finland, the plant is officially
Peganum_harmala
Pharmaceutical compound
analogue of 4-MeO-DMT and a positional isomer of 6-methoxyharmalan and harmaline (7-methoxyharmalan). The drug shows high affinity for the serotonin 5-HT2A
5-Methoxyharmalan
Species of plant
source?] Caapi contains these harmala alkaloids: Harmine, 0.31–8.43% Harmaline, 0.03–0.83% Tetrahydroharmine, 0.05–2.94% These alkaloids of the beta-carboline
Banisteriopsis_caapi
Pharmaceutical version of the traditional Ayahuasca entheogen
pharmaceutical MAOI, such as moclobemide, instead of a plant. DMT and harmaline or harmine are typically used as components of pharmahuasca. One study
Pharmahuasca
Pharmaceutical compound
respectively. This is in notable contrast to other β-carbolines like harmine and harmaline, which are inactive as serotonin 5-HT2A receptor agonists. It is also
1-Ethyl-6-hydroxytryptoline
Pharmaceutical compound
Dimethyltryptamine/β-carbolines, also known as DMT/harmine/harmaline/THH, is a combination of dimethyltryptamine (DMT), a tryptamine serotonin receptor
Dimethyltryptamine/β-carbolines
Dimethyltryptamine/β-carbolines
Pharmaceutical compound
relationship may be seen with the alkaloids of the Harmala group, such as harmaline (VIa; Figure 4). This material along with its dehydro- and dihydro- counterparts
6-Methoxyharman
and synthesizing the harmala alkaloids and hallucinogens harmine and harmaline in 1927 as well as for many other scientific contributions to alkaloid
Richard_Manske
Chemical compound
is reported to be hallucinogenic similarly to other β-carbolines like harmaline. Limited testing suggests that it possesses mild psychoactive effects
6-MeO-THH
1997 book by Alexander Shulgin and Ann Shulgin
like α-methyltryptamine (AMT), β-carbolines or harmala alkaloids like harmaline, the iboga alkaloid ibogaine, and lysergamides like LSD. Whereas PiHKAL
TiHKAL
Psychotic disorder featuring hallucinations
deprivation, sensory deprivation, or drugs (such as the oneirogens ibogaine and harmaline). Oneirophrenia is often confused with an acute case of schizophrenia
Oneirophrenia
DMT-infused smoking blend
reported. The compounds found in seeds of this plant are β-carbolines (harmaline, harmine, harmalol, tetrahydroharmine, and harmol; Herraiz, González,
Changa_(drug)
Class of alkaloids
β-carboline derivatives include harmine, harmaline, harmane and a slightly more complex structure of canthinone. Harmaline was first isolated in 1838 by Göbel
Indole_alkaloid
Chemical compound
in tobacco smoke. Harmane is related to other alkaloids, harmine and harmaline, found in 1837 in the plant Peganum harmala. The name derives from the
Harmane
Chemical compound
as an MAO-A inhibitor in the brain was approximately equal to that of harmaline at equimolar doses. Dextroamphetamine did not enhance the 5-hydroxytryptophan-induced
Α-Methyltryptamine
Anti-hypertension medication
CX157 (Tyrima) Eprobemide Esuprone Harmala alkaloids (e.g., harmine, harmaline, harman, norharman, tetrahydroharmine, 6-methoxyharman) Methylene blue
Hydralazine
Species of plant
has been found to contain β-carbolines such as norharman, harmalol, and harmaline, and harmine, as well as ibogaine. In addition, these constituents were
Silene_undulata
Chilean psychotherapist (1932–2019)
Assessment and Research (IPAR). In the 1960s, Naranjo introduced ibogaine and harmaline into psychotherapy as a "fantasy enhancing drug." Richard Evans Schultes
Claudio_Naranjo
Type of medication
serotonergic activity because MAO-A metabolizes serotonin. Harmine and harmaline, found in Peganum harmala, Banisteriopsis caapi, and Passiflora incarnata
Monoamine_oxidase_inhibitor
Class of drugs
muscimol and gaboxadol Oneirogens (unknown mechanism) like ibogaine and harmaline Cannabinoids (CB1 receptor agonists) like THC, nabilone, and JWH-018 Others
Hallucinogen
Anti-convulsant, anti-addictive CNS stimulant alkaloid
saline control". While the related alkaloids ibogaine (20–40 mg/kg), harmaline (10–40 mg/kg) and desethylcoronaridine (10–40 mg/kg) were "obviously tremorgenic"
Ibogamine
Richard Manske – synthesized DMT and identified and synthesized harmine and harmaline Robert Oberlender – a student in the lab of David E. Nichols who developed
List_of_psychedelic_chemists
Chemical compound
PMID 24368411. El Gendy MA, Soshilov AA, Denison MS, El-Kadi AO (2012). "Harmaline and harmalol inhibit the carcinogen-activating enzyme CYP1A1 via transcriptional
Harmalol
List of plant species with reported psychoactive properties
metallicolor, harmine, telepathine Banisteriopsis muricata, harmine up to 6%, harmaline up to 4%, plus DMT[better source needed] Diplopterys cabrerana, beta-carbolines
List_of_psychoactive_plants
Hallucinogenic class of psychoactive drug
plants containing monoamine oxidase inhibitors (MAOIs), like harmine and harmaline, which allows DMT to be consumed orally without being rendered inactive
Psychedelic_drug
Chemical compound
Conodurine Coronaridine Corydaline Corynoline Crimidine Cyclanoline Cymserine Harmaline Kobophenol A Lactucopicrin Lycorine Phosacetim Rosmarinic acid Stercuronium
A-232
Species of mushroom
ISBN 978-0-578-71442-4. Flattery, David Stophlet; Schwartz, Martin (1989). Haoma and Harmaline: The Botanical Identity of the Indo-Iranian Sacred Hallucinogen 'soma'
Amanita_muscaria
Pakistani chemist
earlier work of the Nobel Laureate Sir Robert Robinson on the chemistry of harmaline. Later in 2007, he was appointed as an honorary life fellow of King's
Atta-ur-Rahman_(chemist)
Monoamine neurotransmitter
6-MeO-THH, 6-methoxyharmalan, 9-Me-BC, β-carboline (norharman), fenharmane, harmaline, harmalol, harmane, harmine, LY-266,097, pinoline, tetrahydroharmine,
Serotonin
second plant was Peganum harmala (harmal, harmel, Syrian rue, see also harmaline), known in Iranian languages as esfand, sepand or other similar terms
Botanical identity of soma–haoma
Botanical_identity_of_soma–haoma
Type of psychoactive fungus
Oneirogens (unknown mech.) Harmala alkaloids/β-carbolines (e.g., harmine, harmaline, tetrahydroharmine, 6-methoxyharmalan, 6-MeO-THH) (found in Peganum harmala
Hallucinogenic bolete mushroom
Hallucinogenic_bolete_mushroom
Chemical compound found in some species of mushrooms
isocarboxazid, and moclobemide, as well as harmala alkaloids like harmine and harmaline and chronic tobacco smoking. An early clinical study of psilocybin in
Psilocybin
Herb in Greek and Roman legend
(Greek πἠγανον), from the seeds and roots of which the vegetable alkaloid harmaline is extracted. The flowers are white with green stripes. Victor Bérard
Moly_(herb)
While not serotonergic psychedelics, the oneirogens and related drugs harmaline and harmalol are also explicitly controlled substances in Canada. In contrast
Legal status of psychedelic drugs in Canada
Legal_status_of_psychedelic_drugs_in_Canada
Genus of flowering plants
alkaloids of the β-carboline group such as harmine, tetrahydroharmine, harmaline, manacine, manaceine, and also derivatives of dimethyltryptamine (DMT)
Brunfelsia
Species of fungus
Oneirogens (unknown mech.) Harmala alkaloids/β-carbolines (e.g., harmine, harmaline, tetrahydroharmine, 6-methoxyharmalan, 6-MeO-THH) (found in Peganum harmala
Lanmaoa_asiatica
Movement disorder that causes involuntary tremors
"Living with a Mild Essential Tremor". Harmaline is a widely used model of essential tremor (ET) in rodents. Harmaline is thought to act primarily on neurons
Essential_tremor
Antibiotic for treatment of tuberculosis
CX157 (Tyrima) Eprobemide Esuprone Harmala alkaloids (e.g., harmine, harmaline, harman, norharman, tetrahydroharmine, 6-methoxyharman) Methylene blue
Isoniazid
Central nervous system stimulant
Conodurine Coronaridine Corydaline Corynoline Crimidine Cyclanoline Cymserine Harmaline Kobophenol A Lactucopicrin Lycorine Phosacetim Rosmarinic acid Stercuronium
Caffeine
Chemical compound
CX157 (Tyrima) Eprobemide Esuprone Harmala alkaloids (e.g., harmine, harmaline, harman, norharman, tetrahydroharmine, 6-methoxyharman) Methylene blue
Zalsupindole
Chemical compound
6-MeO-THH, 6-methoxyharmalan, 9-Me-BC, β-carboline (norharman), fenharmane, harmaline, harmalol, harmane, harmine, LY-266,097, pinoline, tetrahydroharmine,
Bretisilocin
Mushrooms containing psychoactive indole alkaloids
β-carbolines, such as harmine, harmane, tetrahydroharmine (THH), and harmaline, which inhibit monoamine oxidase (MAO), an enzyme that breaks down tryptamine
Psilocybin_mushroom
Chemical compound
Oneirogens (unknown mech.) Harmala alkaloids/β-carbolines (e.g., harmine, harmaline, tetrahydroharmine, 6-methoxyharmalan, 6-MeO-THH) (found in Peganum harmala
Adrenochrome
hyoscyamine, diphenhydramine, trihexyphenidyl) Oneirogens (e.g., ibogaine, harmaline, tetrahydroharmine (THH)) GABAA receptor agonists (e.g., muscimol, gaboxadol)
List_of_psychoactive_drugs
Pharmaceutical compound
"seminal" or "archetypal" psychedelic in PiHKAL. Combination of TMA-2 with harmaline or ibogaine has been reported to result in long-lasting episodes complicated
2,4,5-Trimethoxyamphetamine
Chemical compound and chemical warfare nerve agent
Conodurine Coronaridine Corydaline Corynoline Crimidine Cyclanoline Cymserine Harmaline Kobophenol A Lactucopicrin Lycorine Phosacetim Rosmarinic acid Stercuronium
Sarin
Spice from tree seed
Oneirogens (unknown mech.) Harmala alkaloids/β-carbolines (e.g., harmine, harmaline, tetrahydroharmine, 6-methoxyharmalan, 6-MeO-THH) (found in Peganum harmala
Nutmeg
Chemical compound
Conodurine Coronaridine Corydaline Corynoline Crimidine Cyclanoline Cymserine Harmaline Kobophenol A Lactucopicrin Lycorine Phosacetim Rosmarinic acid Stercuronium
Tabun_(nerve_agent)
Pharmaceutical drug
CX157 (Tyrima) Eprobemide Esuprone Harmala alkaloids (e.g., harmine, harmaline, harman, norharman, tetrahydroharmine, 6-methoxyharman) Methylene blue
Deprenyl
Psychedelic drug
6-MeO-THH, 6-methoxyharmalan, 9-Me-BC, β-carboline (norharman), fenharmane, harmaline, harmalol, harmane, harmine, LY-266,097, pinoline, tetrahydroharmine,
4-HO-DET
Chemical compound
6-MeO-THH, 6-methoxyharmalan, 9-Me-BC, β-carboline (norharman), fenharmane, harmaline, harmalol, harmane, harmine, LY-266,097, pinoline, tetrahydroharmine,
4-HO-DiPT
Psychedelic drug
6-MeO-THH, 6-methoxyharmalan, 9-Me-BC, β-carboline (norharman), fenharmane, harmaline, harmalol, harmane, harmine, LY-266,097, pinoline, tetrahydroharmine,
4-HO-MiPT
Pharmaceutical compound
similar potency as β-carboline but 28- to 85-fold lower potency than harmaline and harmane (1-methyl-β-carboline). In addition, the drug is a lower-potency
1-Ethyl-β-carboline
Species of flowering plant in the nightshade family
alkaloids derived from Beta-carboline such as harmine, tetrahydroharmine, harmaline, manacin, manacein, and dimethyltryptamine and amidine derivatives such
Brunfelsia_pauciflora
Pharmacology of the antiparkinsonian and antidepressant selegiline
CX157 (Tyrima) Eprobemide Esuprone Harmala alkaloids (e.g., harmine, harmaline, harman, norharman, tetrahydroharmine, 6-methoxyharman) Methylene blue
Pharmacology_of_selegiline
Naturally occurring psychedelic compound
Peru. [...] preliminary human bioassays suggest that the β-carboline harmaline might in fact potentiate mescaline - low doses of 60 and 100 mg mescaline
Mescaline
Chemical compound
CX157 (Tyrima) Eprobemide Esuprone Harmala alkaloids (e.g., harmine, harmaline, harman, norharman, tetrahydroharmine, 6-methoxyharman) Methylene blue
Disulfiram
Irreversible non-selective MAO inhibitor and antidepressant drug
CX157 (Tyrima) Eprobemide Esuprone Harmala alkaloids (e.g., harmine, harmaline, harman, norharman, tetrahydroharmine, 6-methoxyharman) Methylene blue
Phenelzine
Species of flowering plant in the nightshade family
Oneirogens (unknown mech.) Harmala alkaloids/β-carbolines (e.g., harmine, harmaline, tetrahydroharmine, 6-methoxyharmalan, 6-MeO-THH) (found in Peganum harmala
Datura_stramonium
Species of plant
Oneirogens (unknown mech.) Harmala alkaloids/β-carbolines (e.g., harmine, harmaline, tetrahydroharmine, 6-methoxyharmalan, 6-MeO-THH) (found in Peganum harmala
Hyoscyamus_niger
Australian legal instrument
Examples: 2C-I Benzylpiperazine Bromo-DragonFLY Coca leaf DMT Harmine/Harmaline Heroin Kratom, also known as Mitragyna speciosa; as well its main alkaloid
Standard for the Uniform Scheduling of Medicines and Poisons
Standard_for_the_Uniform_Scheduling_of_Medicines_and_Poisons
Medication used for migraines & cluster headaches
6-MeO-THH, 6-methoxyharmalan, 9-Me-BC, β-carboline (norharman), fenharmane, harmaline, harmalol, harmane, harmine, LY-266,097, pinoline, tetrahydroharmine,
Sumatriptan
Chemical compound
Oneirogens (unknown mech.) Harmala alkaloids/β-carbolines (e.g., harmine, harmaline, tetrahydroharmine, 6-methoxyharmalan, 6-MeO-THH) (found in Peganum harmala
Glaucine
Class of enzymes
CX157 (Tyrima) Eprobemide Esuprone Harmala alkaloids (e.g., harmine, harmaline, harman, norharman, tetrahydroharmine, 6-methoxyharman) Methylene blue
Aromatic L-amino acid decarboxylase
Aromatic_L-amino_acid_decarboxylase
Pharmaceutical compound
6-MeO-THH, 6-methoxyharmalan, 9-Me-BC, β-carboline (norharman), fenharmane, harmaline, harmalol, harmane, harmine, LY-266,097, pinoline, tetrahydroharmine,
Deuterated_mitragynine
Chemical compound
6-MeO-THH, 6-methoxyharmalan, 9-Me-BC, β-carboline (norharman), fenharmane, harmaline, harmalol, harmane, harmine, LY-266,097, pinoline, tetrahydroharmine,
N-Methyltryptamine
Species of plant
Oneirogens (unknown mech.) Harmala alkaloids/β-carbolines (e.g., harmine, harmaline, tetrahydroharmine, 6-methoxyharmalan, 6-MeO-THH) (found in Peganum harmala
Heimia_salicifolia
Psychedelic drug
6-MeO-THH, 6-methoxyharmalan, 9-Me-BC, β-carboline (norharman), fenharmane, harmaline, harmalol, harmane, harmine, LY-266,097, pinoline, tetrahydroharmine,
DiPT
Chemical compound
CX157 (Tyrima) Eprobemide Esuprone Harmala alkaloids (e.g., harmine, harmaline, harman, norharman, tetrahydroharmine, 6-methoxyharman) Methylene blue
Tritoqualine
Neurotoxin produced by Clostridium botulinum
Conodurine Coronaridine Corydaline Corynoline Crimidine Cyclanoline Cymserine Harmaline Kobophenol A Lactucopicrin Lycorine Phosacetim Rosmarinic acid Stercuronium
Botulinum_toxin
Chemical compound
6-MeO-THH, 6-methoxyharmalan, 9-Me-BC, β-carboline (norharman), fenharmane, harmaline, harmalol, harmane, harmine, LY-266,097, pinoline, tetrahydroharmine,
5-MeO-NET
Pharmaceutical compound
6-MeO-THH, 6-methoxyharmalan, 9-Me-BC, β-carboline (norharman), fenharmane, harmaline, harmalol, harmane, harmine, LY-266,097, pinoline, tetrahydroharmine,
MSP-2020
Endogenous enzyme
alkaloids (Syrian Rue, Passion Flower, Tobacco smoke, Ayahuasca) Harmine Harmaline Isoquinoline alkaloids Piperine (Black pepper) Rosiridin (in vitro) Monoamine
Monoamine_oxidase_A
Brofaromine • Cimoxatone • Clorgiline • Esuprone • Harmala alkaloids (harmine, harmaline, tetrahydroharmine, harman, norharman, etc.) • Methylene blue • Metralindole •
List_of_dopaminergic_drugs
Chemical compound
CX157 (Tyrima) Eprobemide Esuprone Harmala alkaloids (e.g., harmine, harmaline, harman, norharman, tetrahydroharmine, 6-methoxyharman) Methylene blue
Amodiaquine
Medication for overactive bladder
Oneirogens (unknown mech.) Harmala alkaloids/β-carbolines (e.g., harmine, harmaline, tetrahydroharmine, 6-methoxyharmalan, 6-MeO-THH) (found in Peganum harmala
Oxybutynin
Pharmaceutical compound
6-MeO-THH, 6-methoxyharmalan, 9-Me-BC, β-carboline (norharman), fenharmane, harmaline, harmalol, harmane, harmine, LY-266,097, pinoline, tetrahydroharmine,
Pharm-136
Pharmaceutical compound
6-MeO-THH, 6-methoxyharmalan, 9-Me-BC, β-carboline (norharman), fenharmane, harmaline, harmalol, harmane, harmine, LY-266,097, pinoline, tetrahydroharmine,
4-Bromo-DMT
86386–73–4 C13H12O β-ionone 2484–16–4 C13H12O2 monobenzone 103–16–2 C13H14N2O harmaline C13H16N2O2 melatonin 73–31–4 C13H18O2 ibuprofen 15687–27–1 C13H28 tridecane
Glossary_of_chemical_formulae
Drug that binds to but does not activate muscarinic cholinergic receptors
Oneirogens (unknown mech.) Harmala alkaloids/β-carbolines (e.g., harmine, harmaline, tetrahydroharmine, 6-methoxyharmalan, 6-MeO-THH) (found in Peganum harmala
Muscarinic_antagonist
Chemical compound
Conodurine Coronaridine Corydaline Corynoline Crimidine Cyclanoline Cymserine Harmaline Kobophenol A Lactucopicrin Lycorine Phosacetim Rosmarinic acid Stercuronium
Diisopropyl_paraoxon
Series of nerve agents developed by the Soviet Union
Conodurine Coronaridine Corydaline Corynoline Crimidine Cyclanoline Cymserine Harmaline Kobophenol A Lactucopicrin Lycorine Phosacetim Rosmarinic acid Stercuronium
Novichok
include the following: β-Carbolines and harmala alkaloids such as harmine, harmaline, tetrahydroharmine (THH), 6-methoxyharmalan, and 6-MeO-THH Iboga alkaloids
List_of_hallucinogens
Chemical compound
CX157 (Tyrima) Eprobemide Esuprone Harmala alkaloids (e.g., harmine, harmaline, harman, norharman, tetrahydroharmine, 6-methoxyharman) Methylene blue
Ampyzine
Vedic ritual drink
Oneirogens (unknown mech.) Harmala alkaloids/β-carbolines (e.g., harmine, harmaline, tetrahydroharmine, 6-methoxyharmalan, 6-MeO-THH) (found in Peganum harmala
Soma_(drink)
Pharmaceutical compound
6-MeO-THH, 6-methoxyharmalan, 9-Me-BC, β-carboline (norharman), fenharmane, harmaline, harmalol, harmane, harmine, LY-266,097, pinoline, tetrahydroharmine,
4-HO-NET
Chemical compound
CX157 (Tyrima) Eprobemide Esuprone Harmala alkaloids (e.g., harmine, harmaline, harman, norharman, tetrahydroharmine, 6-methoxyharman) Methylene blue
9-Methyl-β-carboline
Monoamine metabolism inhibitor
CX157 (Tyrima) Eprobemide Esuprone Harmala alkaloids (e.g., harmine, harmaline, harman, norharman, tetrahydroharmine, 6-methoxyharman) Methylene blue
Α-Methylphenylalanine
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HARMALINE
HARMALINE
HARMALINE
HARMALINE
HARMALINE
HARMALINE
HARMALINE
HARMALINE
HARMALINE
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