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Tetrahydrocannabivarin

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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 Formula	C₁₉H₂₆O₂
Molecular Weight	286.4 g/mol
XLogP3	5.9
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	2
Exact Mass	286.193280068 g/mol
Monoisotopic Mass	286.193280068 g/mol
Topological Polar Surface Area	29.5 Å²
Heavy Atom Count	21
Formal Charge	0
Complexity	412
Isotope Atom Count	0
Defined Atom Stereocenter Count	2
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

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.

Drugs in Development