A harmala alkaloid
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Analytical Standard(s)
35037Tetrahydroharmine
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Product Type

Natural Products
Alkaloids
Small Molecule Modulators
Small Molecule Inhibitors

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Application

Tetrahydroharmine

Item No. 14449

Product Insert (PDF)GC-MS (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2,3,4,9-tetrahydro-7-methoxy-1-methyl-1H-pyrido[3,4-b]indole
CAS Number
17019-01-1
Synonyms
  • Leptaflorine
  • THH
Molecular Formula
C13H16N2O
Formula Weight
216.3
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 1.5 mg/mlDMSO: 2 mg/mlEthanol: 1.5 mg/mlPBS (pH 7.2): 0.25 mg/ml
λmax
228, 271, 299 nm
SMILES
CC(NCC1)C2=C1C(C=CC(OC)=C3)=C3N2
InChi Code
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
InChi Key
ZXLDQJLIBNPEFJ-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    5 mg

    $51

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    10 mg

    $87

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    25 mg

    $179

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    50 mg

    $329

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    Product Description

    Tetrahydroharmine (THH) is a fluorescent indole alkaloid extracted from B. caapi, a woody vine that is used to produce a psychoactive beverage, ayahuasca, which has been ritually ingested for medicoreligious purposes throughout South America since pre-Columbian times.1 THH inhibits monoamine oxidase (MAO)-A and MAO-B with much weaker potency (IC50s = 74 nM and >100 μM, respectively) compared to the companion harmala alkaloids also found in B. caapi: harmaline (Item No. 10995; IC50s = 2.5 nM and 25 μM, respectively) and harmine (Item No. 10010324; IC50s = 2 nM and 20 μM, respectively).2,3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Callaway, J.C., Raymon, L.P., Hearn, W.L., et al. Quantitation of N,N-dimethyltryptamine and harmala alkaloids in human plasma after oral dosing with Ayahuasca. J. Anal. Toxicol. 20(6), 492-497 (1996).

    2. Samoylenko, V., Rahman, M.M., Tekwani, B.L., et al. Banisteriopsis caapi, a unique combination of MAO inhibitory and antioxidative constituents for the activities relevant to neurodegenerative disorders and Parkinson’s disease. J. Ethnopharmacol. 127(2), 357-367 (2010).

    3. Wang, Y.H., Samoylenko, V., Tekwani, B.L., et al. Composition, standardization and chemical profiling of Banisteriopsis caapi, a plant for the treatment of neurodegenerative disorders relevant to Parkinson’s disease. J. Ethnopharmacol. 128(3), 661-671 (2010).