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Tetrahydrocannabivarin

HCID 93147
NotesReactions
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
31262-37-0
Standard SMILES
CCCc1cc(O)c2c(c1)OC(C)(C)[C@@H]1CCC(C)=C[C@@H]21
InChIKey
ZROLHBHDLIHEMS-HUUCEWRRSA-N
Molecular formula
C19H26O2
Average molar mass
286.4 g/mol
Monoisotopic mass
286.19328007

Overview

Tetrahydrocannabivarin (THCV) is a propyl analogue of tetrahydrocannabinol (Δ9-THC), one of the primary pharmacological components of [Medical Cannabis]. Δ9-THC is currently available in several synthetic forms, including [Dronabinol], while purified or isolated THCV is not approved for any medical uses and is not available as any marketed products. As a major phytocannabinoid, however, THCV is accessible within [Medical Cannabis] along with other identified cannabinoids including [Cannabidiol] (CBD), [cannabinol] (CBN), [cannabigerol] (CBG), [cannabichromene] (CBC), [cannabivarin] (CBV), and [Cannabidivarin] (CBDV). THCV is one of four cannabinoids with identified potential as anticonvulsant agents, which also includes Δ9-tetrahydrocannabinolic acid, [Cannabidiol] (CBD), and [Cannabidivarin] (CBDV). Although THCV possesses an almost identical structure to Δ9-THC (varying only by the length of its lipophilic alkyl chain), it has different molecular targets and pharmacological profile. Compared to THC which demonstrates its effects through weak partial agonist activity of both endocannabinoid receptors Cannabinoid-1 (CB1R) and Cannabinoid-2 (CB2R), 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-α-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 TRPV2, which may contribute to the analgesic, anti-inflammatory and anti-cancer effects of cannabinoids and Cannabis extracts. It has also shown antiepileptiform and anticonvulsant properties, that suggest possible therapeutic application in the treatment of pathophysiologic hyperexcitability states such as untreatable epilepsy. Cannabinoid receptors are utilized endogenously by the body through the endocannabinoid system, which includes a group of lipid proteins, enzymes, and receptors that are involved in many physiological processes. Through its modulation of neurotransmitter release, the endocannabinoid system regulates cognition, pain sensation, appetite, memory, sleep, immune function, and mood among many others. These effects are largely mediated through two members of the G-protein coupled receptor family, cannabinoid receptors 1 and 2 (CB1 and CB2). CB1 receptors are found in both the central and peripheral nervous systems, with the majority of receptors localized to the hippocampus and amygdala of the brain. Physiological effects of using cannabis make sense in the context of its receptor activity as the hippocampus and amygdala are primarily involved with regulation of memory, fear, and emotion. In contrast, CB2 receptors are mainly found peripherally in immune cells, lymphoid tissue, and peripheral nerve terminals. Reliably studying the effects of Cannabis (and of THCV) is complicated by the numerous other compounds that Cannabis contains such as terpenes, flavonoids, phenols, amino acids, and fatty acids among many others that have the potential to modulate the plant's pharmacological effect.

Names & identifiers

Preferred name
Tetrahydrocannabivarin
IUPAC
(6aR,10aR)-6,6,9-trimethyl-3-propyl-6a,7,8,10a-tetrahydrobenzo[c]chromen-1-ol
English name
Delta9-tetrahydrocannabivarin
Molecular formula
C19H26O2
Molecular weight
286.41

Names & synonyms

TETRAHYDROCANNABIVARIN31262-37-0delta9-TetrahydrocannabivarinTHCVTHC-V.delta.9-Tetrahydrocannabivarin(6aR,10aR)-6,6,9-trimethyl-3-propyl-6a,7,8,10a-tetrahydrobenzo[c]chromen-1-olGWP42004GWP-42004I5YE3I47D8O-4394Cannabivarol, .delta.9-tetrahydro-
Show more names
Δ9-TetrahydrocannabivarinTetrahydrocannavarinΔ9-TetrahydrocannabivarolΔ1-TetrahydrocannabidivarolTetrahydrocannabivarin(THCV)Tetrahydrocannabivarin (CRM)Δ9-trans-Tetrahydrocannabivarin
(-)-.delta.9-trans-Tetrahydrocannabivarin(6aR,10aR)-6,6,9-trimethyl-3-propyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromen-1-ol(6aR,10aR)-6,6,9-trimethyl-3-propyl-6a,7,8,10a-tetrahydro-6H-dibenzo[b,d]pyran-1-ol6H-Dibenzo(b,d)pyran-1-ol, 6a,7,8,10a-tetrahydro-6,6,9-trimethyl-3-propyl-, (6aR-trans)-6H-Dibenzo[b,d]pyran-1-ol, 6a,7,8,10a-tetrahydro-6,6,9-trimethyl-3-propyl-, (6aR-trans)-UNII-I5YE3I47D86H-DIBENZO(B,D)PYRAN-1-OL, 6A,7,8,10A-TETRAHYDRO-6,6,9-TRIMETHYL-3-PROPYL-, (6AR,10AR)-6H-Dibenzo[b,d]pyran-1-ol, 6a,7,8,10a-tetrahydro-6,6,9-trimethyl-3-propyl-, (6aR,10aR)-

Database identifiers

Properties

Computed structural properties

XLogP
5.9
Topological polar surface area
29.5 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
2
Rotatable bonds
2
Heavy atoms
21
Formal charge
0
Complexity
412

Experimental & physicochemical properties

Drugs · 2 items

DEA NFLIS-Drug Category -> Cannabinoids

Pharmaceuticals -> Listed in ZINC15

Endocrine DisruptorsPotential endocrine disrupting compound

Physicochemical properties

Boiling point
360.6 · 360.6±42.0 °C(Predicted)
Density
1.034 · 1.034±0.06 g/cm3(Predicted)
solubility
10 mg/ml · Methanol: 10 mg/ml
pka
9.79 · 9.79±0.60(Predicted)
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
InChIKey
ZROLHBHDLIHEMS-HUUCEWRRSA-N
SMILES
C12=CC(CCC)=CC(O)=C1[C@]1([H])C=C(C)CC[C@@]1([H])C(C)(C)O2
FDA UNII
5 YE3I47D8 · I5YE3I47D8
Symbol(GHS)
9 · GHS09
Signal word
Warning

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 4 items

Warning

H400 (100%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]

P273, P391, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 38 reports by companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Hazard Classes and CategoriesAquatic Acute 1 (100%)

Safety data

Signal word
Warning
Symbol(GHS)
GHS09
Hazard statements
H410
Precautionary statements
P273-P391-P501

Chemistry & industry

Pharmacology

Pharmacodynamics · 1 item

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-α-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.

Applications

DescriptionTetrahydrocannabivarin (CRM) (Item No. 18091) is a certified reference material categorized as a phytocannabinoid. This product is intended for research and forensic applications.

Upstream & downstream products

Upstream raw materials

6H-Dibenzo[b,d]pyran-1-ol, 6a,7,8,10a-tetrahydro-6,6,9-trimethyl-3-propyl-, 1-(4-methylbenzenesulfonate), (6aR,10aR)-Cannabidivarol

Suppliers19 total

广州佳途科技股份有限公司81960175-877 18933936954 · [email protected]
武汉众志诚生物技术有限公司13628624121 13628604890 · [email protected]

Related reactions

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
CAS
31262-37-0
PubChem CID
93147
DTXSID
DTXSID10893920
ChEMBL
CHEMBL2387541
UNII
I5YE3I47D8
EC Number
809-026-4
Nikkaji
J108.077F
Hazard statements
410 · H410
Precautionary statements
273 · P273-P391-P501
Baoji Guokang Healthchem co.,ltd+8615604608665 15604608665 · [email protected]
安耐吉化学&3A(安徽泽升科技有限公司)021-58432009 400-005-6266 · [email protected]
云南西力生物技术股份有限公司0871-65217109 · [email protected]
金瓯生物医药(南京)有限公司13000000000 · [email protected]
泰州布莱泽生物医药科技有限公司0523-86112008 13915404123 · [email protected]
泰州布莱泽生物医药科技有限公司0523-86112008 13915404123 · [email protected]
济南药研药物化学有限公司[email protected]
南京美韬医药科技有限公司[email protected] · [email protected]
上海博湖生物科技有限公司021-57763112 13585886131 · [email protected]
南京康满林化工实业有限公司025-83697070 13770331960 · [email protected]
四川百奥克睿生物科技有限公司28-86-28-8543-3893 13260669172 · [email protected]
上海同田生物技术有限公司021-51320588 · [email protected]
上海陶术生物科技股份有限公司+1-781-999-5354 · [email protected]
北京新研汇医药研发有限公司13969155946 · [email protected]
南京世洲生物科技有限公司025-85560043 15850508050 · [email protected]
上海禾午生物科技有限公司021-57886085 17317861055 · [email protected]
山东子易医药有限公司13173053288 · [email protected]