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    Tetrahydrocannabivarin

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    PharmaCompass
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    2D Structure
    Also known as: 31262-37-0, Delta9-tetrahydrocannabivarin, Thcv, Thc-v, .delta.9-tetrahydrocannabivarin, (6ar,10ar)-6,6,9-trimethyl-3-propyl-6a,7,8,10a-tetrahydrobenzo[c]chromen-1-ol
    Molecular Formula
    C19H26O2
    Molecular Weight
    286.4  g/mol
    InChI Key
    ZROLHBHDLIHEMS-HUUCEWRRSA-N
    FDA UNII
    I5YE3I47D8
    tetrahydrocannabivarin is a natural product found in Cannabis sativa with data available.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (6aR,10aR)-6,6,9-trimethyl-3-propyl-6a,7,8,10a-tetrahydrobenzo[c]chromen-1-ol
    2.1.2 InChI
    InChI=1S/C19H26O2/c1-5-6-13-10-16(20)18-14-9-12(2)7-8-15(14)19(3,4)21-17(18)11-13/h9-11,14-15,20H,5-8H2,1-4H3/t14-,15-/m1/s1
    2.1.3 InChI Key
    ZROLHBHDLIHEMS-HUUCEWRRSA-N
    2.1.4 Canonical SMILES
    CCCC1=CC(=C2C3C=C(CCC3C(OC2=C1)(C)C)C)O
    2.1.5 Isomeric SMILES
    CCCC1=CC(=C2[C@@H]3C=C(CC[C@H]3C(OC2=C1)(C)C)C)O
    2.2 Other Identifiers
    2.2.1 UNII
    I5YE3I47D8
    2.3 Synonyms
    2.3.1 Depositor-Supplied Synonyms

    1. 31262-37-0

    2. Delta9-tetrahydrocannabivarin

    3. Thcv

    4. Thc-v

    5. .delta.9-tetrahydrocannabivarin

    6. (6ar,10ar)-6,6,9-trimethyl-3-propyl-6a,7,8,10a-tetrahydrobenzo[c]chromen-1-ol

    7. Gwp42004

    8. Gwp-42004

    9. I5ye3i47d8

    10. O-4394

    11. Cannabivarol, .delta.9-tetrahydro-

    12. (-)-.delta.9-trans-tetrahydrocannabivarin

    13. 6h-dibenzo(b,d)pyran-1-ol, 6a,7,8,10a-tetrahydro-6,6,9-trimethyl-3-propyl-, (6ar-trans)-

    14. 6h-dibenzo[b,d]pyran-1-ol, 6a,7,8,10a-tetrahydro-6,6,9-trimethyl-3-propyl-, (6ar-trans)-

    15. Unii-i5ye3i47d8

    16. 6h-dibenzo(b,d)pyran-1-ol, 6a,7,8,10a-tetrahydro-6,6,9-trimethyl-3-propyl-, (6ar,10ar)-

    17. 6h-dibenzo[b,d]pyran-1-ol, 6a,7,8,10a-tetrahydro-6,6,9-trimethyl-3-propyl-, (6ar,10ar)-

    18. Delta9-thcv

    19. .delta.9-tetrahydrocannabivarol

    20. Gtpl6418

    21. Schembl6856739

    22. Chembl2387541

    23. .delta.1-tetrahydrocannabidivarol

    24. Dtxsid10893920

    25. 6h-dibenzo(b,d)pyran-1-ol, 6a,7,8,10a-tetrahydro-6,6,9-trimethyl-3-propyl-

    26. Zinc5649505

    27. Bdbm50511105

    28. Hy-u00342

    29. .delta.9-trans-tetrahydrocannabivarin

    30. Cannabidivarol, .delta.1-tetrahydro-

    31. Cs-7377

    32. Db11755

    33. 6h-dibenzo[b,d]pyran-1-ol, 6a,7,8,10a-tetrahydro-6,6,9-trimethyl-3-propyl-, (-)-

    34. Delta9-tetrahydrocannabivarin (thcv) 10 Microg/ml In Methanol

    35. Delta9-tetrahydrocannabivarin (thcv) 100 Ug/ml In Methanol

    36. Delta9-tetrahydrocannabivarin (thcv) 1000 Ug/ml In Methanol

    37. Delta9-tetrahydrocannabivarin (thcv) 250 Microg/ml In Acetonitrile

    38. (6ar,10ar)-6,6,9-trimethyl-3-propyl-6h,6ah,7h,8h,10ah-benzo[c]isochromen-1-ol

    39. 6,6,9-trimethyl-3-propyl-6a,7,8,10a-tetrahydro-6h-benzo[c]chromen-1-ol-, (6ar-trans)-

    2.4 Create Date
    2005-08-08
    3 Chemical and Physical Properties
    Molecular Weight 286.4 g/mol
    Molecular Formula C19H26O2
    XLogP35.9
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count2
    Rotatable Bond Count2
    Exact Mass286.193280068 g/mol
    Monoisotopic Mass286.193280068 g/mol
    Topological Polar Surface Area29.5 Ų
    Heavy Atom Count21
    Formal Charge0
    Complexity412
    Isotope Atom Count0
    Defined Atom Stereocenter Count2
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Indication

    THCV does not currently have any FDA, Health Canada, or EMA approved indications.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Compared to THC which demonstrates its effects through weak partial agonist activity at Cannabinoid-1 (CB1R) and Cannabinoid-2 (CB2R) receptors, THCV acts as a CB1 antagonist and a partial agonist of CB2. Further evidence has also shown that THCV acts as an agonist of GPR55 and l--lysophosphatidylinositol (LPI). Beyond the endocannabinoid system, THCV has also been reported to activate 5HT1A receptors to produce an antipsychotic effect that has therapeutic potential for ameliorating some of the negative, cognitive and positive symptoms of schizophrenia. Furthermore, THCV interacts with different transient receptor potential (TRP) channels including TRPV1, which may contribute to the analgesic, anti-inflammatory and anti-cancer effects of cannabinoids and Cannabis extracts.