11-Hydroxytetrahydrocannabinol
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Basic information
- CAS
34675-49-5- Standard SMILES
CCCCCc1cc(O)c2c(c1)OC(C)(C)[C@@H]1CCC(CO)=C[C@@H]21- InChIKey
YCBKSSAWEUDACY-IAGOWNOFSA-N- Molecular formula
- C21H30O3
- Average molar mass
- 330.5 g/mol
- Monoisotopic mass
- 330.21949481
Overview
11-hydroxy-Delta(9)-tetrahydrocannabinol is a phytocannabinoid that is 9-tetrahydrocannabinol in which the methyl group at C-11 has been hydroxylated. Major metabolite of 9-tetrahydrocannabinol. It has a role as a human xenobiotic metabolite. It is functionally related to a Delta(9)-tetrahydrocannabinol.
Names & identifiers
- Preferred name
- 11-Hydroxytetrahydrocannabinol
- IUPAC
- (6aR,10aR)-9-(hydroxymethyl)-6,6-dimethyl-3-pentyl-6a,7,8,10a-tetrahydrobenzo[c]chromen-1-ol
- English name
- 11-Hydroxytetrahydrocannabinol
- Molecular formula
- C21H30O3
- Molecular weight
- 330.46
Names & synonyms
11-Hydroxytetrahydrocannabinol36557-05-834675-49-511-Hydroxy-DELTA9-tetrahydrocannabinol11-Hydroxy-delta9-THC11-Hydroxy-delta(sup 9)tetrahydrocannabinol9VY04N5SLB(+/-)-11-hydroxy-Delta9-THC (CRM)7-Hydroxy-delta(sup 1)tetrahydrocannabinol11-Hydroxy-.DELTA.9-THC(-)-11-hydroxy-Delta(9)-THC(6aR,10aR)-9-(hydroxymethyl)-6,6-dimethyl-3-pentyl-6a,7,8,10a-tetrahydrobenzo[c]chromen-1-ol
Show more names
(±)-11-hydroxy-Δ9-THC(±)-trans-11-OH-Δ9-THC(-11-hydroxy-9-THC (CRM)(±)-11-hydroxy-Δ9-THC (CRM)(±)-11-hydroxy-Δ9-THC (CRM)(±)-11-Hydroxy-Δ9-THC solution(±)-11-Hydroxy-Δ9-THC solution(±)-11-Hydroxy-Δ9-THC solutiond,l-11-Hydroxy-delta-9-THC, 1mg/ml in Methanol
(6aR,10aR)-6a,7,8,10a-Tetrahydro-1-hydroxy-6,6-dimethyl-3-pentyl-6H-dibenzo[b,d]pyran-9-methanol11-Hydroxy-.DELTA.9-tetrahydrocannabinol(-)-11-hydroxy-Delta(9)-tetrahydrocannabinol6H-Dibenzo[b,d]pyran-9-methanol, 6a,7,8,10a-tetrahydro-1-hydroxy-6,6-dimethyl-3-pentyl-, (6aR-trans)-6H-Dibenzo[b,d]pyran-9-methanol,6a,7,8,10a-tetrahydro-1-hydroxy-6,6-dimethyl-3-pentyl-,(6aR,10aR)-rel-UNII-9VY04N5SLB(?)-11-hydroxy-?9-THC7-Hydroxy-delta1-tetrahydrocannabinol
Properties
Computed structural propertiesFilling in
- XLogP
- 5.7
- Topological polar surface area
- 49.7 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 5
- Heavy atoms
- 24
- Formal charge
- 0
- Complexity
- 456
Experimental & physicochemical properties
LogP5.33
Endocrine DisruptorsPotential endocrine disrupting compound
Physicochemical properties
- Boiling point
- 437.1 · 437.1±45.0 °C(Predicted)
- Density
- 1.071 · 1.071±0.06 g/cm3(Predicted)
- Flash point
- 9 ℃ · 9℃
- storage temp.
- 2 · 2-8°C
- pka
- 9.78 · 9.78±0.60(Predicted)
- form
- liquid
- Major Application
- cannabis testingforensics and toxicology
- InChI
- 1S/C21H30O3/c1-4-5-6-7-14-11-18(23)20-16-10-15(13-22)8-9-17(16)21(2,3)24-19(20)12-14/h10-12,16-17,22-23H,4-9,13H2,1-3H3
- InChIKey
- YCBKSSAWEUDACY-UHFFFAOYSA-N
- SMILES
- OC1=CC(CCCCC)=CC2=C1C3C=C(CO)CCC3C(O2)(C)C
- UNSPSC Code
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
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P203, P264, P270, P280, P301+P317, P318, P330, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 40 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
Hazard information
Hazard Classes and Categories
Acute Tox. 4 (100%)
Acute Tox. 4 (100%)
Safety data
- wgk
- 1
- ridadr
- UN1230 - class 3 - PG 2 - Methanol, solution
- risk_code
- 11-23/24/25-39/23/24/25
- Signal word
- Danger
- Symbol(GHS)
- GHS02,GHS06,GHS08
- hazard_code
- F,T
- safety_code
- 7-16-36/37-45
- Storage Class
- 3 - Flammable liquids
- target organs
- Eyes,Central nervous system
- Hazard statements
- H225-H301+H311+H331-H370
- Hazard Classifications
- Acute Tox. 3 DermalAcute Tox. 3 InhalationAcute Tox. 3 OralFlam. Liq. 2STOT SE 1
- Precautionary statements
- P210-P260-P280-P301+P310-P311
Chemistry & industry
Pharmacology
Metabolism/Metabolites11-hydroxy-delata-Tetrahydrocannabinol is a known human metabolite of delta-9-Tetrahydrocannabinol.
Applications
UsesThe Certified Spiking Solution(R) is suitable for (±)-11-Hydroxy-Δ9-THC testing by HPLC, GC/MS, or LC-MS/MS methods in forensic analysis, clinical toxicology, urine drug testing, and Cannabis potency or impurity profiling testing applications. The Certified Reference Material (CRM) in solution can also be used as follows:Quantification of cannabidiol and Δ9-tetrahydrocannabinol in addition to the identification of minor cannabinoids from human plasma samples using ultra-performance liquid chromatography (UHPLC) combined with triple quadrupole mass spectrometry following a liquid-liquid extractionLiquid chromatography-tandem mass spectrometry (LC-MS/MS) method-based determination of 10 cannabinoids in oral fluid samples following their solid phase extraction (SPE)Analysis of Δ9-Tetrahydrocannabinol (Δ9-THC) and its three metabolites in plasma and urine samples by gas chromatography (GC) coupled to triple quadrupole mass spectrometerDevelopment of an automated sample preparation method based on solid phase extraction (SPE) to determine ∆9-tetrahydrocannabinol (THC) and its three primary metabolites in a variety of matrices, such as serum, saliva, and urine using liquid chromatography-mass spectrometry (LC-MS)Simultaneous determination of cannabinoids and their metabolites in human serum samples by an atmospheric-pressure chemical ionization gas chromatography-tandem mass spectrometry (APGC-MS/MS)
Additional notes
DefinitionChEBI: 11-hydroxy-Delta(9)-tetrahydrocannabinol is a phytocannabinoid that is Delta(9)-tetrahydrocannabinol in which the methyl group at C-11 has been hydroxylated. Major metabolite of Delta(9)-tetrahydrocannabinol. It has a role as a human xenobiotic metabolite. It is functionally related to a Delta(9)-tetrahydrocannabinol.
Related reactions
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Compound notes
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