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Tetrahydrocannabivarin
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

Tetrahydrocannabivarin

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.


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