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Chemical compound
Tetrahydroharmine (THH), also known as 7-methoxy-1,2,3,4-tetrahydroharman (7-MeO-THH), is a fluorescent indole alkaloid and β-carboline that occurs in
Tetrahydroharmine
Species of plant
harmaline, tetrahydroharmine, and to a lesser extent, harmine. The stems contain 0.11–0.83% beta-carbolines, with harmine and tetrahydroharmine as the major
Banisteriopsis_caapi
Group of chemical compounds
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
Harmala_alkaloid
Chemical compound
particularly hallucinogenic, although other compounds such as harmine and tetrahydroharmine (THH) have also been reported to produce hallucinogenic effects as
Harmaline
South American psychoactive decoction
certain doses. Tetrahydroharmine is a harmala alkaloid found in organisms such as Daphnia pulex and Euglena gracilis. Tetrahydroharmine, a component of
Ayahuasca
Pharmaceutical compound
like LSD but similar to those of ibogaine. Along with harmaline and tetrahydroharmine, harmine is one of the psychoactive constituents of Banisteriopsis
Harmine
Pharmaceutical compound
and reversible inhibitors of MAO-A (RIMAs) harmine, harmaline, and tetrahydroharmine (THH), which is under development for potential medical use. It is
Dimethyltryptamine/β-carbolines
Dimethyltryptamine/β-carbolines
DMT-infused smoking blend
seeds of this plant are β-carbolines (harmaline, harmine, harmalol, tetrahydroharmine, and harmol; Herraiz, González, Ancín-Azpilicueta, Arán, & Guillén
Changa_(drug)
Chemical compound
been referred to as oneirogens. These include harmine, harmaline, tetrahydroharmine, 6-methoxyharmalan, and 6-methoxytetrahydroharman (6-MeO-THH). According
Substituted_β-carboline
Topics referred to by the same term
refer to: Hillingdon Hospital, west London, England (opened 1838) Tetrahydroharmine, a fluorescent alkaloid chemical Thomas Henry Huxley (1825–1895),
THH
Chemical compound
more specifically a pinoline) derivative and a structural isomer of tetrahydroharmine (7-MeO-THH). It is mentioned in Alexander Shulgin's book TiHKAL (Tryptamines
6-MeO-THH
Species of plant
can grow from 6 to 12 feet. The plant is a psychedelic, containing tetrahydroharmine (also known as leptaflorin) which is a monoamine oxidase inhibitor
Leptactina_densiflora
List of plant species with reported psychoactive properties
etc. Kochia scoparia, harman; Harmine, etc. Guiera senegalensis, tetrahydroharmine; Harman, etc. Carex brevicollis, harmine, etc. Carex parva, beta-carbolines
List_of_psychoactive_plants
Mushrooms containing psychoactive indole alkaloids
mushrooms are found to produce β-carbolines, such as harmine, harmane, tetrahydroharmine (THH), and harmaline, which inhibit monoamine oxidase (MAO), an enzyme
Psilocybin_mushroom
Spice from Myristica fragrans
mech.) Harmala alkaloids/β-carbolines (e.g., harmine, harmaline, tetrahydroharmine, 6-methoxyharmalan, 6-MeO-THH) (found in Peganum harmala, Banisteriopsis
Nutmeg
Monoamine neurotransmitter
fenharmane, harmaline, harmalol, harmane, harmine, LY-266,097, pinoline, tetrahydroharmine, tryptoline) Iboga alkaloids (e.g., ibogaine, ibogamine, noribogaine
Serotonin
Species of flowering plant in the nightshade family
mech.) Harmala alkaloids/β-carbolines (e.g., harmine, harmaline, tetrahydroharmine, 6-methoxyharmalan, 6-MeO-THH) (found in Peganum harmala, Banisteriopsis
Datura_stramonium
contrast, other oneirogens including ibogaine, noribogaine, harmine, tetrahydroharmine, and 6-MeO-THH are all not controlled substances. However, Health
Legal status of psychedelic drugs in Canada
Legal_status_of_psychedelic_drugs_in_Canada
Psychedelic drug
Ayahuasca Alkaloids N,N-Dimethyltryptamine (DMT), Harmine, Harmaline and Tetrahydroharmine: Clinical and Forensic Impact". Pharmaceuticals. 13 (11): 334. doi:10
Dimethyltryptamine
following: β-Carbolines and harmala alkaloids such as harmine, harmaline, tetrahydroharmine (THH), 6-methoxyharmalan, and 6-MeO-THH Iboga alkaloids such as ibogaine
List_of_hallucinogens
Species of fungus
mech.) Harmala alkaloids/β-carbolines (e.g., harmine, harmaline, tetrahydroharmine, 6-methoxyharmalan, 6-MeO-THH) (found in Peganum harmala, Banisteriopsis
Lanmaoa_asiatica
Chemical compound
Esuprone Harmala alkaloids (e.g., harmine, harmaline, harman, norharman, tetrahydroharmine, 6-methoxyharman) Methylene blue Metralindole Minaprine Moclobemide
Disulfiram
Deadly nightshade, a flowering plant
mech.) Harmala alkaloids/β-carbolines (e.g., harmine, harmaline, tetrahydroharmine, 6-methoxyharmalan, 6-MeO-THH) (found in Peganum harmala, Banisteriopsis
Atropa_bella-donna
Genus of poisonous, potentially psychoactive plants
mech.) Harmala alkaloids/β-carbolines (e.g., harmine, harmaline, tetrahydroharmine, 6-methoxyharmalan, 6-MeO-THH) (found in Peganum harmala, Banisteriopsis
Datura
Drug class
mech.) Harmala alkaloids/β-carbolines (e.g., harmine, harmaline, tetrahydroharmine, 6-methoxyharmalan, 6-MeO-THH) (found in Peganum harmala, Banisteriopsis
Κ-Opioid_receptor_agonist
Psychedelic drug found in toads, mushrooms and plants
fenharmane, harmaline, harmalol, harmane, harmine, LY-266,097, pinoline, tetrahydroharmine, tryptoline) Iboga alkaloids (e.g., ibogaine, ibogamine, noribogaine
Bufotenin
Species of flowering plant in the nightshade family
contain indole alkaloids derived from Beta-carboline such as harmine, tetrahydroharmine, harmaline, manacin, manacein, and dimethyltryptamine and amidine
Brunfelsia_pauciflora
Hallucinogenic class of psychoactive drug
Ayahuasca Alkaloids N,N-Dimethyltryptamine (DMT), Harmine, Harmaline and Tetrahydroharmine: Clinical and Forensic Impact". Pharmaceuticals (Basel). 13 (11):
Psychedelic_drug
Species of mushroom
mech.) Harmala alkaloids/β-carbolines (e.g., harmine, harmaline, tetrahydroharmine, 6-methoxyharmalan, 6-MeO-THH) (found in Peganum harmala, Banisteriopsis
Amanita_muscaria
Antibiotic for treatment of tuberculosis
Esuprone Harmala alkaloids (e.g., harmine, harmaline, harman, norharman, tetrahydroharmine, 6-methoxyharman) Methylene blue Metralindole Minaprine Moclobemide
Isoniazid
Chemical compound found in some species of mushrooms
fenharmane, harmaline, harmalol, harmane, harmine, LY-266,097, pinoline, tetrahydroharmine, tryptoline) Iboga alkaloids (e.g., ibogaine, ibogamine, noribogaine
Psilocybin
Chemical compound
fenharmane, harmaline, harmalol, harmane, harmine, LY-266,097, pinoline, tetrahydroharmine, tryptoline) Iboga alkaloids (e.g., ibogaine, ibogamine, noribogaine
Yohimbine
Tropane alkaloid & anticholinergic drug
mech.) Harmala alkaloids/β-carbolines (e.g., harmine, harmaline, tetrahydroharmine, 6-methoxyharmalan, 6-MeO-THH) (found in Peganum harmala, Banisteriopsis
Scopolamine
Chemical compound
mech.) Harmala alkaloids/β-carbolines (e.g., harmine, harmaline, tetrahydroharmine, 6-methoxyharmalan, 6-MeO-THH) (found in Peganum harmala, Banisteriopsis
Adrenochrome
Psychedelic drug
fenharmane, harmaline, harmalol, harmane, harmine, LY-266,097, pinoline, tetrahydroharmine, tryptoline) Iboga alkaloids (e.g., ibogaine, ibogamine, noribogaine
Psilocin
Drug that produces a dream-like state of consciousness
root)) β-Carbolines and harmala alkaloids such as harmine, harmaline, tetrahydroharmine (THH), 6-methoxyharmalan, and 6-MeO-THH (some of the preceding found
Oneirogen
Serotonergic psychedelic
fenharmane, harmaline, harmalol, harmane, harmine, LY-266,097, pinoline, tetrahydroharmine, tryptoline) Iboga alkaloids (e.g., ibogaine, ibogamine, noribogaine
Deudimethyltryptamine
Use of drugs with the primary intention to alter the state of consciousness
mech.) Harmala alkaloids/β-carbolines (e.g., harmine, harmaline, tetrahydroharmine, 6-methoxyharmalan, 6-MeO-THH) (found in Peganum harmala, Banisteriopsis
Recreational_drug_use
Type of medication
Esuprone Harmala alkaloids (e.g., harmine, harmaline, harman, norharman, tetrahydroharmine, 6-methoxyharman) Methylene blue Metralindole Minaprine Moclobemide
Monoamine_oxidase_inhibitor
Psychoactive component of cannabis
mech.) Harmala alkaloids/β-carbolines (e.g., harmine, harmaline, tetrahydroharmine, 6-methoxyharmalan, 6-MeO-THH) (found in Peganum harmala, Banisteriopsis
Tetrahydrocannabinol
Cimoxatone • Clorgiline • Esuprone • Harmala alkaloids (harmine, harmaline, tetrahydroharmine, harman, norharman, etc.) • Methylene blue • Metralindole • Minaprine •
List_of_dopaminergic_drugs
Medication for overactive bladder
mech.) Harmala alkaloids/β-carbolines (e.g., harmine, harmaline, tetrahydroharmine, 6-methoxyharmalan, 6-MeO-THH) (found in Peganum harmala, Banisteriopsis
Oxybutynin
Chemical compound
fenharmane, harmaline, harmalol, harmane, harmine, LY-266,097, pinoline, tetrahydroharmine, tryptoline) Iboga alkaloids (e.g., ibogaine, ibogamine, noribogaine
4-HO-MET
Blue dye also used as a medication
Esuprone Harmala alkaloids (e.g., harmine, harmaline, harman, norharman, tetrahydroharmine, 6-methoxyharman) Methylene blue Metralindole Minaprine Moclobemide
Methylene_blue
Species of plant
mech.) Harmala alkaloids/β-carbolines (e.g., harmine, harmaline, tetrahydroharmine, 6-methoxyharmalan, 6-MeO-THH) (found in Peganum harmala, Banisteriopsis
Heimia_salicifolia
Agricultural product processed from the leaves of plants in the genus Nicotiana
Esuprone Harmala alkaloids (e.g., harmine, harmaline, harman, norharman, tetrahydroharmine, 6-methoxyharman) Methylene blue Metralindole Minaprine Moclobemide
Tobacco
Ionotropic receptor and ligand-gated ion channel
Inverse allosteric agonists: beta-carbolines (e.g., harmine, harmaline, tetrahydroharmine). Second-order modulators: (−)‐epigallocatechin‐3‐gallate. Non-competitive
GABAA_receptor
Psychedelic tryptamine
fenharmane, harmaline, harmalol, harmane, harmine, LY-266,097, pinoline, tetrahydroharmine, tryptoline) Iboga alkaloids (e.g., ibogaine, ibogamine, noribogaine
5-MeO-DiPT
Chemical compound
fenharmane, harmaline, harmalol, harmane, harmine, LY-266,097, pinoline, tetrahydroharmine, tryptoline) Iboga alkaloids (e.g., ibogaine, ibogamine, noribogaine
Luvesilocin
Class of pharmaceutical drugs
fenharmane, harmaline, harmalol, harmane, harmine, LY-266,097, pinoline, tetrahydroharmine, tryptoline) Iboga alkaloids (e.g., ibogaine, ibogamine, noribogaine
Triptan
Metabolite of the amino acid tryptophan
fenharmane, harmaline, harmalol, harmane, harmine, LY-266,097, pinoline, tetrahydroharmine, tryptoline) Iboga alkaloids (e.g., ibogaine, ibogamine, noribogaine
Tryptamine
Class of indoles
fenharmane, harmaline, harmalol, harmane, harmine, LY-266,097, pinoline, tetrahydroharmine, tryptoline) Iboga alkaloids (e.g., ibogaine, ibogamine, noribogaine
Substituted_tryptamine
Pharmaceutical compound
fenharmane, harmaline, harmalol, harmane, harmine, LY-266,097, pinoline, tetrahydroharmine, tryptoline) Iboga alkaloids (e.g., ibogaine, ibogamine, noribogaine
Tabernanthalog
Antihistamine medication
mech.) Harmala alkaloids/β-carbolines (e.g., harmine, harmaline, tetrahydroharmine, 6-methoxyharmalan, 6-MeO-THH) (found in Peganum harmala, Banisteriopsis
Diphenhydramine
Medication
Esuprone Harmala alkaloids (e.g., harmine, harmaline, harman, norharman, tetrahydroharmine, 6-methoxyharman) Methylene blue Metralindole Minaprine Moclobemide
Selegiline
Species of plant
mech.) Harmala alkaloids/β-carbolines (e.g., harmine, harmaline, tetrahydroharmine, 6-methoxyharmalan, 6-MeO-THH) (found in Peganum harmala, Banisteriopsis
Hyoscyamus_niger
Experimental cardiovascular drug
Esuprone Harmala alkaloids (e.g., harmine, harmaline, harman, norharman, tetrahydroharmine, 6-methoxyharman) Methylene blue Metralindole Minaprine Moclobemide
Zamicastat
Plant species in the family
Harmaline 7-Methoxy-3,4-dihydroharman 150–400 mg 100% 70–150 mg 5–8 hours Tetrahydroharmine 7-Methoxy-1,2,3,4-tetrahydroharman ≥300 mg ~33% Unknown Unknown 6-Methoxyharmalan
Peganum_harmala
Genus of flowering plants
include indole alkaloids of the β-carboline group such as harmine, tetrahydroharmine, harmaline, manacine, manaceine, and also derivatives of dimethyltryptamine
Brunfelsia
Species of plant
mech.) Harmala alkaloids/β-carbolines (e.g., harmine, harmaline, tetrahydroharmine, 6-methoxyharmalan, 6-MeO-THH) (found in Peganum harmala, Banisteriopsis
Salvia_divinorum
Pharmaceutical compound
fenharmane, harmaline, harmalol, harmane, harmine, LY-266,097, pinoline, tetrahydroharmine, tryptoline) Iboga alkaloids (e.g., ibogaine, ibogamine, noribogaine
4-HO-NET
Chemical compound
Esuprone Harmala alkaloids (e.g., harmine, harmaline, harman, norharman, tetrahydroharmine, 6-methoxyharman) Methylene blue Metralindole Minaprine Moclobemide
Zalsupindole
Ancient Greek drink
mech.) Harmala alkaloids/β-carbolines (e.g., harmine, harmaline, tetrahydroharmine, 6-methoxyharmalan, 6-MeO-THH) (found in Peganum harmala, Banisteriopsis
Kykeon
Pharmaceutical drug
mech.) Harmala alkaloids/β-carbolines (e.g., harmine, harmaline, tetrahydroharmine, 6-methoxyharmalan, 6-MeO-THH) (found in Peganum harmala, Banisteriopsis
Mefloquine
Chemical compound
fenharmane, harmaline, harmalol, harmane, harmine, LY-266,097, pinoline, tetrahydroharmine, tryptoline) Iboga alkaloids (e.g., ibogaine, ibogamine, noribogaine
Tryptophan
Anti-hypertension medication
Esuprone Harmala alkaloids (e.g., harmine, harmaline, harman, norharman, tetrahydroharmine, 6-methoxyharman) Methylene blue Metralindole Minaprine Moclobemide
Hydralazine
Species of plant
mech.) Harmala alkaloids/β-carbolines (e.g., harmine, harmaline, tetrahydroharmine, 6-methoxyharmalan, 6-MeO-THH) (found in Peganum harmala, Banisteriopsis
Tabernanthe_iboga
Entheogenic use of marijuana
mech.) Harmala alkaloids/β-carbolines (e.g., harmine, harmaline, tetrahydroharmine, 6-methoxyharmalan, 6-MeO-THH) (found in Peganum harmala, Banisteriopsis
Cannabis_and_religion
Anticholinergic medication used as antidote for nerve agent poisoning
mech.) Harmala alkaloids/β-carbolines (e.g., harmine, harmaline, tetrahydroharmine, 6-methoxyharmalan, 6-MeO-THH) (found in Peganum harmala, Banisteriopsis
Atropine
Antispasmodic agent
mech.) Harmala alkaloids/β-carbolines (e.g., harmine, harmaline, tetrahydroharmine, 6-methoxyharmalan, 6-MeO-THH) (found in Peganum harmala, Banisteriopsis
Dicycloverine
Mechanism of psychoactive drugs mimicking the symptoms of psychosis
mech.) Harmala alkaloids/β-carbolines (e.g., harmine, harmaline, tetrahydroharmine, 6-methoxyharmalan, 6-MeO-THH) (found in Peganum harmala, Banisteriopsis
Psychotomimetism
Chemical compound
fenharmane, harmaline, harmalol, harmane, harmine, LY-266,097, pinoline, tetrahydroharmine, tryptoline) Iboga alkaloids (e.g., ibogaine, ibogamine, noribogaine
Speciociliatine
Military incapacitating agent
mech.) Harmala alkaloids/β-carbolines (e.g., harmine, harmaline, tetrahydroharmine, 6-methoxyharmalan, 6-MeO-THH) (found in Peganum harmala, Banisteriopsis
3-Quinuclidinyl_benzilate
Substance related to dopamine functions
rasagiline, as well as the harmala alkaloids like harmine, harmaline, tetrahydroharmine, harmalol, harman, and norharman, which are found to varying degrees
Dopaminergic
Antispasmodic drug
mech.) Harmala alkaloids/β-carbolines (e.g., harmine, harmaline, tetrahydroharmine, 6-methoxyharmalan, 6-MeO-THH) (found in Peganum harmala, Banisteriopsis
Trihexyphenidyl
Irreversible non-selective MAO inhibitor and antidepressant drug
Esuprone Harmala alkaloids (e.g., harmine, harmaline, harman, norharman, tetrahydroharmine, 6-methoxyharman) Methylene blue Metralindole Minaprine Moclobemide
Phenelzine
Chemical compound
mech.) Harmala alkaloids/β-carbolines (e.g., harmine, harmaline, tetrahydroharmine, 6-methoxyharmalan, 6-MeO-THH) (found in Peganum harmala, Banisteriopsis
Glaucine
Endogenous enzyme
Esuprone Harmala alkaloids (e.g., harmine, harmaline, harman, norharman, tetrahydroharmine, 6-methoxyharman) Methylene blue Metralindole Minaprine Moclobemide
Monoamine_oxidase_A
Pharmaceutical drug
Esuprone Harmala alkaloids (e.g., harmine, harmaline, harman, norharman, tetrahydroharmine, 6-methoxyharman) Methylene blue Metralindole Minaprine Moclobemide
Deprenyl
Psychedelic drug
fenharmane, harmaline, harmalol, harmane, harmine, LY-266,097, pinoline, tetrahydroharmine, tryptoline) Iboga alkaloids (e.g., ibogaine, ibogamine, noribogaine
DiPT
Chemical compound
mech.) Harmala alkaloids/β-carbolines (e.g., harmine, harmaline, tetrahydroharmine, 6-methoxyharmalan, 6-MeO-THH) (found in Peganum harmala, Banisteriopsis
Meclizine
Psychedelic drug
fenharmane, harmaline, harmalol, harmane, harmine, LY-266,097, pinoline, tetrahydroharmine, tryptoline) Iboga alkaloids (e.g., ibogaine, ibogamine, noribogaine
MSP-1014
Psychedelic drug
fenharmane, harmaline, harmalol, harmane, harmine, LY-266,097, pinoline, tetrahydroharmine, tryptoline) Iboga alkaloids (e.g., ibogaine, ibogamine, noribogaine
4-HO-DET
Psychoactive substance found in plants in the family Apocynaceae
mech.) Harmala alkaloids/β-carbolines (e.g., harmine, harmaline, tetrahydroharmine, 6-methoxyharmalan, 6-MeO-THH) (found in Peganum harmala, Banisteriopsis
Ibogaine
Antidepressant
Esuprone Harmala alkaloids (e.g., harmine, harmaline, harman, norharman, tetrahydroharmine, 6-methoxyharman) Methylene blue Metralindole Minaprine Moclobemide
Iproniazid
Serotonin receptor agonist
fenharmane, harmaline, harmalol, harmane, harmine, LY-266,097, pinoline, tetrahydroharmine, tryptoline) Iboga alkaloids (e.g., ibogaine, ibogamine, noribogaine
4-Hydroxytryptamine
Vedic ritual drink
mech.) Harmala alkaloids/β-carbolines (e.g., harmine, harmaline, tetrahydroharmine, 6-methoxyharmalan, 6-MeO-THH) (found in Peganum harmala, Banisteriopsis
Soma_(drink)
Chemical compound
fenharmane, harmaline, harmalol, harmane, harmine, LY-266,097, pinoline, tetrahydroharmine, tryptoline) Iboga alkaloids (e.g., ibogaine, ibogamine, noribogaine
Bretisilocin
fenharmane, harmaline, harmalol, harmane, harmine, LY-266,097, pinoline, tetrahydroharmine, tryptoline) Iboga alkaloids (e.g., ibogaine, ibogamine, noribogaine
List_of_psychedelic_drugs
diphenhydramine, trihexyphenidyl) Oneirogens (e.g., ibogaine, harmaline, tetrahydroharmine (THH)) GABAA receptor agonists (e.g., muscimol, gaboxadol) κ-Opioid
List_of_psychoactive_drugs
Hormone released by the pineal gland
fenharmane, harmaline, harmalol, harmane, harmine, LY-266,097, pinoline, tetrahydroharmine, tryptoline) Iboga alkaloids (e.g., ibogaine, ibogamine, noribogaine
Melatonin
Chemical compound
mech.) Harmala alkaloids/β-carbolines (e.g., harmine, harmaline, tetrahydroharmine, 6-methoxyharmalan, 6-MeO-THH) (found in Peganum harmala, Banisteriopsis
Cryogenine
Pharmaceutical compound
fenharmane, harmaline, harmalol, harmane, harmine, LY-266,097, pinoline, tetrahydroharmine, tryptoline) Iboga alkaloids (e.g., ibogaine, ibogamine, noribogaine
5-MeO-NiPT
Protein-coding gene in the species Homo sapiens
Esuprone Harmala alkaloids (e.g., harmine, harmaline, harman, norharman, tetrahydroharmine, 6-methoxyharman) Methylene blue Metralindole Minaprine Moclobemide
Monoamine_oxidase_B
Tropane alkaloid
mech.) Harmala alkaloids/β-carbolines (e.g., harmine, harmaline, tetrahydroharmine, 6-methoxyharmalan, 6-MeO-THH) (found in Peganum harmala, Banisteriopsis
Hyoscyamine
Opioid medication
mech.) Harmala alkaloids/β-carbolines (e.g., harmine, harmaline, tetrahydroharmine, 6-methoxyharmalan, 6-MeO-THH) (found in Peganum harmala, Banisteriopsis
Pentazocine
Type of psychoactive fungus
mech.) Harmala alkaloids/β-carbolines (e.g., harmine, harmaline, tetrahydroharmine, 6-methoxyharmalan, 6-MeO-THH) (found in Peganum harmala, Banisteriopsis
Hallucinogenic bolete mushroom
Hallucinogenic_bolete_mushroom
Chemical compound
fenharmane, harmaline, harmalol, harmane, harmine, LY-266,097, pinoline, tetrahydroharmine, tryptoline) Iboga alkaloids (e.g., ibogaine, ibogamine, noribogaine
N-Methyltryptamine
Class of psychoactive drugs
mech.) Harmala alkaloids/β-carbolines (e.g., harmine, harmaline, tetrahydroharmine, 6-methoxyharmalan, 6-MeO-THH) (found in Peganum harmala, Banisteriopsis
Deliriant
First-generation antihistamine used as a short-term sedative and hypnotic (sleep aid)
mech.) Harmala alkaloids/β-carbolines (e.g., harmine, harmaline, tetrahydroharmine, 6-methoxyharmalan, 6-MeO-THH) (found in Peganum harmala, Banisteriopsis
Doxylamine
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