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Tetrahydroharmine information


Tetrahydroharmine
Clinical data
Other namesTHH; 1,2,3,4-Tetrahydroharmine; Leptaflorine; 2,3,4,9-Tetrahydro-7-methoxy-1-methyl-1H-pyrido(3,4-b)indole
Legal status
Legal status
  • AU: S9 (Prohibited substance)
Identifiers
IUPAC name
  • 7-methoxy-1-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole
CAS Number
  • 17019-01-1
PubChem CID
  • 159809
ChemSpider
  • 140510
UNII
  • F1Q1E0G45A
KEGG
  • C09243
ChEBI
  • CHEBI:311931
ChEMBL
  • ChEMBL129208
Chemical and physical data
FormulaC13H16N2O
Molar mass216.284 g·mol−1
3D model (JSmol)
  • Interactive image
SMILES
  • CC1C2=C(CCN1)C3=C(N2)C=C(C=C3)OC
InChI
  • InChI=1S/C13H16N2O/c1-8-13-11(5-6-14-8)10-4-3-9(16-2)7-12(10)15-13/h3-4,7-8,14-15H,5-6H2,1-2H3
  • Key:ZXLDQJLIBNPEFJ-UHFFFAOYSA-N

Tetrahydroharmine (THH) is a fluorescent indole alkaloid that occurs in the tropical liana species Banisteriopsis caapi.[1]

THH, like other harmala alkaloids in B. caapi, namely harmaline and harmine, is a reversible inhibitor of monoamine oxidase A (RIMA),[2] but it also inhibits the reuptake of serotonin.[3]

THH contributes to B. caapi's psychoactivity as a serotonin reuptake inhibitor.[4]

  1. ^ Callaway JC (June 2005). "Various alkaloid profiles in decoctions of Banisteriopsis caapi". Journal of Psychoactive Drugs. 37 (2): 151–155. doi:10.1080/02791072.2005.10399796. PMID 16149328. S2CID 1420203.
  2. ^ Buckholtz NS, Boggan WO (November 1977). "Monoamine oxidase inhibition in brain and liver produced by beta-carbolines: structure-activity relationships and substrate specificity". Biochemical Pharmacology. 26 (21). Elsevier BV: 1991–1996. doi:10.1016/0006-2952(77)90007-7. PMID 921812.
  3. ^ Morales-García JA, de la Fuente Revenga M, Alonso-Gil S, Rodríguez-Franco MI, Feilding A, Perez-Castillo A, Riba J (July 2017). "The alkaloids of Banisteriopsis caapi, the plant source of the Amazonian hallucinogen Ayahuasca, stimulate adult neurogenesis in vitro". Scientific Reports. 7 (1). Springer Science and Business Media LLC: 5309. Bibcode:2017NatSR...7.5309M. doi:10.1038/s41598-017-05407-9. PMC 5509699. PMID 28706205.
  4. ^ Callaway JC, McKenna DJ, Grob CS, Brito GS, Raymon LP, Poland RE, et al. (June 1999). "Pharmacokinetics of Hoasca alkaloids in healthy humans". Journal of Ethnopharmacology. 65 (3): 243–256. doi:10.1016/S0378-8741(98)00168-8. PMID 10404423.

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Tetrahydroharmine

Last Update:

Tetrahydroharmine (THH) is a fluorescent indole alkaloid that occurs in the tropical liana species Banisteriopsis caapi. THH, like other harmala alkaloids...

Word Count : 324

Harmala alkaloid

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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...

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Banisteriopsis caapi

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following harmala alkaloids: Harmine, 0.31–8.43% Harmaline, 0.03–0.83% Tetrahydroharmine, 0.05–2.94% These alkaloids of the beta-carboline class act as monoamine...

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Ayahuasca

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caapi is rich with harmala alkaloids, such as harmine, harmaline and tetrahydroharmine (THH), which can act as a monoamine oxidase inhibitor (MAOi). This...

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List of psychoactive plants

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etc. Kochia scoparia, Harman; Harmine, etc. Guiera senegalensis, Tetrahydroharmine; Harman, etc. Carex brevicollis, Harmine, etc. Carex parva, Beta-carbolines...

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THH

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refer to: Hillingdon Hospital, west London, England (opened 1838) Tetrahydroharmine, a fluorescent alkaloid chemical Thomas Henry Huxley (1825–1895),...

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Harmaline

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imprisonment for a term not exceeding eighteen months. Harmalol Ibogamine Tetrahydroharmine, a similar harmala alkaloid "Peganum Harmala pamphlet: Syrian Rue"...

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Peganum harmala

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Beta-carboline Content 1-hydroxy-7-methoxy-β-carboline 2-aldehyde-tetrahydroharmine 3-hydroxylated harmine 6-methoxytetrahydro-1-norharmanone 8-hydroxy-harmine...

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Dopaminergic

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pargyline, as well as the harmala alkaloids like harmine, harmaline, tetrahydroharmine, harmalol, harman, and norharman, which are found to varying degrees...

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Brunfelsia pauciflora

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

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GABAA receptor

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Inverse allosteric agonists: beta-carbolines (e.g., harmine, harmaline, tetrahydroharmine). Second-order modulators: (−)‐epigallocatechin‐3‐gallate. Non-competitive...

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Disulfiram

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Esuprone Harmala alkaloids (e.g., harmine, harmaline, harman, norharman, tetrahydroharmine) Methylene blue Metralindole Minaprine Moclobemide Pirlindole Sercloremine...

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TiHKAL

Last Update:

PRO-LAD 6-Propyl-NL 52 pyr-T N,N-Tetramethylene-T 53 T Tryptamine 54 Tetrahydroharmine 7-Methoxy-1-methyl-1,2,3,4-tetrahydro-C 55 alpha,N,O-TMS alpha,N-Dimethyl-5-methoxy-T...

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Tobacco

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Esuprone Harmala alkaloids (e.g., harmine, harmaline, harman, norharman, tetrahydroharmine) Methylene blue Metralindole Minaprine Moclobemide Pirlindole Sercloremine...

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Brunfelsia

Last Update:

include indole alkaloids of the β-carboline group such as harmine, tetrahydroharmine, harmaline, manacine, manaceine, and also derivatives of N,N-dimethyltryptamine...

Word Count : 896

Monoamine oxidase inhibitor

Last Update:

Esuprone Harmala alkaloids (e.g., harmine, harmaline, harman, norharman, tetrahydroharmine) Methylene blue Metralindole Minaprine Moclobemide Pirlindole Sercloremine...

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List of dopaminergic drugs

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Cimoxatone • Clorgiline • Esuprone • Harmala alkaloids (harmine, harmaline, tetrahydroharmine, harman, norharman, etc.) • Methylene blue • Metralindole • Minaprine •...

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Hydralazine

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Esuprone Harmala alkaloids (e.g., harmine, harmaline, harman, norharman, tetrahydroharmine) Methylene blue Metralindole Minaprine Moclobemide Pirlindole Sercloremine...

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Santo Daime

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consumed and an MAOI (monoamine oxidase inhibitor), in this case tetrahydroharmine, harmine and harmaline, is needed to allow it to reach the brain in...

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Mepacrine

Last Update:

Esuprone Harmala alkaloids (e.g., harmine, harmaline, harman, norharman, tetrahydroharmine) Methylene blue Metralindole Minaprine Moclobemide Pirlindole Sercloremine...

Word Count : 1451

Harmine

Last Update:

Esuprone Harmala alkaloids (e.g., harmine, harmaline, harman, norharman, tetrahydroharmine) Methylene blue Metralindole Minaprine Moclobemide Pirlindole Sercloremine...

Word Count : 2016

Selegiline

Last Update:

Esuprone Harmala alkaloids (e.g., harmine, harmaline, harman, norharman, tetrahydroharmine) Methylene blue Metralindole Minaprine Moclobemide Pirlindole Sercloremine...

Word Count : 5266

Methylene blue

Last Update:

Esuprone Harmala alkaloids (e.g., harmine, harmaline, harman, norharman, tetrahydroharmine) Methylene blue Metralindole Minaprine Moclobemide Pirlindole Sercloremine...

Word Count : 5613

Leptactina densiflora

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can grow from 6 to 12 feet. The plant is a psychedelic, containing tetrahydroharmine (also known as leptaflorin) which is a monoamine oxidase inhibitor...

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Monoamine oxidase A

Last Update:

Esuprone Harmala alkaloids (e.g., harmine, harmaline, harman, norharman, tetrahydroharmine) Methylene blue Metralindole Minaprine Moclobemide Pirlindole Sercloremine...

Word Count : 4627

Diphenhydramine

Last Update:

Esuprone Harmala alkaloids (e.g., harmine, harmaline, harman, norharman, tetrahydroharmine) Methylene blue Metralindole Minaprine Moclobemide Pirlindole Sercloremine...

Word Count : 6157

Phenelzine

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Esuprone Harmala alkaloids (e.g., harmine, harmaline, harman, norharman, tetrahydroharmine) Methylene blue Metralindole Minaprine Moclobemide Pirlindole Sercloremine...

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