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T2386

Sigma-Aldrich

Δ9-Tetrahydrocannabinol solution

ethanol solution

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Synonym(s):
Δ1-Tetrahydrocannabinol
Empirical Formula (Hill Notation):
C21H30O2
CAS Number:
Molecular Weight:
314.46
MDL number:
PubChem Substance ID:
NACRES:
NA.77

form

ethanol solution

Quality Level

drug control

USDEA Schedule I; Home Office Schedule 2; stupéfiant (France); kontrollierte Droge in Deutschland; regulated under CDSA - not available from Sigma-Aldrich Canada; psicótropo (Spain); Decreto Lei 15/93: Tabela IIB (Portugal)

concentration

25 mg/mL (+/- 5%)

storage temp.

−20°C

SMILES string

[H][C@@]12CCC(C)=C[C@@]1([H])c3c(O)cc(CCCCC)cc3OC2(C)C

InChI

1S/C21H30O2/c1-5-6-7-8-15-12-18(22)20-16-11-14(2)9-10-17(16)21(3,4)23-19(20)13-15/h11-13,16-17,22H,5-10H2,1-4H3/t16-,17-/m1/s1

InChI key

CYQFCXCEBYINGO-IAGOWNOFSA-N

Gene Information

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Application

Δ9-tetrahydrocannabinol solution has been used to study its effects on schizophrenia-related behaviors in a developmental mouse model of schizophrenia.

Biochem/physiol Actions

Δ9-Tetrahydrocannabinol or Δ9-THC is a psychoactive ingredient in marijuana that is known to function as a neuroprotective antioxidant21. In vivo microdialysis studies have reported that Δ9-THC can enhance extracellular dopamine efflux in the nucleus accumbens of conscious, freely-moving rats22.
Agonist at CB1 and CB2 cannabinoid receptors. Hallucinogen; major psychoactive component of marijuana from Cannabis sativa.

Features and Benefits

This compound is featured on the Cannabinoid Receptors page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Preparation Note

Δ9-Tetrahydrocannabinol solution is essentially insoluble in water.

pictograms

FlameExclamation mark

signalword

Danger

Hazard Classifications

Eye Irrit. 2 - Flam. Liq. 2

Storage Class

3 - Flammable liquids

wgk_germany

WGK 2

flash_point_f

57.2 °F

flash_point_c

14 °C

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter


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Exo-tetrahydrocannabinol United States Pharmacopeia (USP) Reference Standard

USP

1090014

Exo-tetrahydrocannabinol

exo-THC solution 1.0 mg/mL in methanol, ampule of 1 mL, certified reference material, Cerilliant®

Supelco

T-033

exo-THC solution

HU-210 solid (air sensitive)

Sigma-Aldrich

H7909

HU-210

J P Chen et al.
Psychopharmacology, 102(2), 156-162 (1990-01-01)
This study examined the effects of acute administration of delta-9-tetrahydrocannabinol (delta 9-THC), the psychoactive ingredient in marijuana, on extracellular efflux of dopamine (DA) and its metabolites as measured by in vivo microdialysis in nucleus accumbens of conscious, freely-moving rats. delta
Delta9-tetrahydrocannabinol (Delta9-THC) administration after neonatal exposure to phencyclidine potentiates schizophrenia-related behavioral phenotypes in mice.
Rodriguez G, et al.
Pharmacology, Biochemistry, and Behavior, 159, 6-11 (2017)
A J Hampson et al.
Proceedings of the National Academy of Sciences of the United States of America, 95(14), 8268-8273 (1998-07-08)
The neuroprotective actions of cannabidiol and other cannabinoids were examined in rat cortical neuron cultures exposed to toxic levels of the excitatory neurotransmitter glutamate. Glutamate toxicity was reduced by both cannabidiol, a nonpsychoactive constituent of marijuana, and the psychotropic cannabinoid
Nafsika Poulia et al.
British journal of pharmacology, 178(7), 1722-1736 (2021-01-27)
Adolescent cannabis use is associated with adult psychopathology. When Δ9 -tetrahydrocannabinol (THC), mainly in high doses, is administered to adolescence rats there are also long lasting effects in adults. This study aims to determine the specific adult bio-behavioural profile after
Going to pot.
Roxanne Khamsi
Scientific American, 308(6), 34-34 (2013-06-05)

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