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Details

Stereochemistry ABSOLUTE
Molecular Formula 2C21H30O2.C4H6O4
Molecular Weight 747.0114
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DRONABINOL HEMISUCCINATE

SMILES

OC(=O)CCC(O)=O.CCCCCC1=CC(O)=C2[C@@H]3C=C(C)CC[C@H]3C(C)(C)OC2=C1.CCCCCC4=CC(O)=C5[C@@H]6C=C(C)CC[C@H]6C(C)(C)OC5=C4

InChI

InChIKey=ZTNSQRHQTPQSCH-VKLRDTKISA-N
InChI=1S/2C21H30O2.C4H6O4/c2*1-5-6-7-8-15-12-18(22)20-16-11-14(2)9-10-17(16)21(3,4)23-19(20)13-15;5-3(6)1-2-4(7)8/h2*11-13,16-17,22H,5-10H2,1-4H3;1-2H2,(H,5,6)(H,7,8)/t2*16-,17-;/m11./s1

HIDE SMILES / InChI

Molecular Formula C4H6O4
Molecular Weight 118.088
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C21H30O2
Molecular Weight 314.4617
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Dronabinol also known as (−)-trans-delta9-tetrahydrocannabinol is an active ingredient of cannabis. The drug was approved by FDA for the treatment of anorexia in patients with AIDS and chemotherapy-induced nausea and vomiting. Dronabinol exerts its action by activating CB1 and CB2 recepors which makes it a CNS active medicine.

CNS Activity

Originator

Approval Year

PubMed

PubMed

TitleDatePubMed
(R)-methanandamide and Delta 9-THC as discriminative stimuli in rats: tests with the cannabinoid antagonist SR-141716 and the endogenous ligand anandamide.
2001 Aug
Marijuana smoke and Delta(9)-tetrahydrocannabinol promote necrotic cell death but inhibit Fas-mediated apoptosis.
2001 Aug 1
CB1 cannabinoid receptor-mediated neurite remodeling in mouse neuroblastoma N1E-115 cells.
2001 Aug 15
Screening method for 11-nor-delta9-tetrahydrocannabinol-9-carboxylic acid in urine using hollow fiber membrane solvent microextraction with in-tube derivatization.
2001 Aug 25
Endogenous cannabinoid, 2-arachidonoylglycerol, attenuates naloxone-precipitated withdrawal signs in morphine-dependent mice.
2001 Aug 3
Activation of the CB1 cannabinoid receptor protects cultured mouse spinal neurons against excitotoxicity.
2001 Aug 31
Cannabinoid receptors are absent in insects.
2001 Aug 6
Delta 9-tetrahydrocannabinol-induced MAPK/ERK and Elk-1 activation in vivo depends on dopaminergic transmission.
2001 Jul
High rates of midazolam self-administration in squirrel monkeys.
2001 Jul
Chronic treatment with Delta(9)-tetrahydrocannabinol enhances the locomotor response to amphetamine and heroin. Implications for vulnerability to drug addiction.
2001 Jul
The pharmacological activity of inhalation exposure to marijuana smoke in mice.
2001 Jul 1
SPME-GC analysis of THC in saliva samples collected with "EPITOPE" device.
2001 Jul 15
Hemodynamic effects of cannabinoids: coronary and cerebral vasodilation mediated by cannabinoid CB(1) receptors.
2001 Jul 6
Cannabinoids for control of chemotherapy induced nausea and vomiting: quantitative systematic review.
2001 Jul 7
Involvement of somatodendritic 5-HT(1A) receptors in Delta(9)-tetrahydrocannabinol-induced hypothermia in the rat.
2001 Jul-Aug
Interaction between delta-9-tetrahydrocannabinol and indomethacin.
2001 Jul-Aug
Concordance between verbal report and urine screen of recent marijuana use in adolescents.
2001 Jul-Aug
Activation of type II cannabinoid receptors improves myocardial tolerance to arrhythmogenic effects of coronary occlusion and reperfusion.
2001 Jun
Cannabinoid receptor agonist and antagonist effects on motor function in normal and 1-methyl-4-phenyl-1,2,5,6-tetrahydropyridine (MPTP)-treated non-human primates.
2001 Jun
Critical role of the endogenous cannabinoid system in mouse pup suckling and growth.
2001 May 11
Delta9-tetrahydrocannabinol enhances cortical and hippocampal acetylcholine release in vivo: a microdialysis study.
2001 May 11
Interactions between A-9THC and capsaicin on isolated lamb bladder detrusor.
2001 May-Jul
[Antiarrhythmic properties of a cannabinoid (CB) receptor agonist].
2001 May-Jun
[Passive exposure in detection of low blood and urine cannabinoid concentrations].
2001 May-Jun
Cannabinoid-induced motor incoordination through the cerebellar CB(1) receptor in mice.
2001 May-Jun
Delta-9-tetrahydrocannabinol differentially suppresses cisplatin-induced emesis and indices of motor function via cannabinoid CB(1) receptors in the least shrew.
2001 May-Jun
Precipitated cannabinoid withdrawal is reversed by Delta(9)-tetrahydrocannabinol or clonidine.
2001 May-Jun
Delta9-tetrahydrocannabivarin as a marker for the ingestion of marijuana versus Marinol: results of a clinical study.
2001 Oct
A comparison of Roche Kinetic Interaction of Microparticles in Solution (KIMS) assay for cannabinoids and GC-MS analysis for 11-nor-9-carboxy-delta9-tetrahydrocannabinol.
2001 Oct
The determination of 11-nor-delta9-tetrahydrocannabinol-9-carboxylic acid (THC-COOH) in hair using negative ion gas chromatography-mass spectrometry and high-volume injection.
2001 Oct
Solid-phase extraction and GC-MS analysis of THC-COOH method optimized for a high-throughput forensic drug-testing laboratory.
2001 Oct
Temporal indication of marijuana use can be estimated from plasma and urine concentrations of delta9-tetrahydrocannabinol, 11-hydroxy-delta9-tetrahydrocannabinol, and 11-nor-delta9-tetrahydrocannabinol-9-carboxylic acid.
2001 Oct
Simultaneous determination of delta9-tetrahydrocannabinol and 11-nor-9-carboxy-delta9-tetrahydrocannabinol in human plasma by solid-phase extraction and gas chromatography-negative ion chemical ionization-mass spectrometry.
2001 Oct
A cannabinoid mechanism in relapse to cocaine seeking.
2001 Oct
Cannabinoid activity curtails cocaine craving.
2001 Oct
Electrophysiological evidence of serotonergic impairment in long-term MDMA ("ecstasy") users.
2001 Oct
Marijuana abstinence effects in marijuana smokers maintained in their home environment.
2001 Oct
Neuropsychological performance in long-term cannabis users.
2001 Oct
Ethanol increases plasma Delta(9)-tetrahydrocannabinol (THC) levels and subjective effects after marihuana smoking in human volunteers.
2001 Oct 1
Differential effects of delta 9-THC on spatial reference and working memory in mice.
2001 Sep
The psychoactive ingredient of marijuana induces behavioural sensitization.
2001 Sep
Identification and quantitation of 11-nor-delta9-tetrahydrocannabivarin-9-carboxylic acid, a major metabolite of delta9-tetrahydrocannabivarin.
2001 Sep
Role of gonadal steroids in the corticotropin-releasing hormone and proopiomelanocortin gene expression response to Delta(9)-tetrahydrocannabinol in the hypothalamus of the rat.
2001 Sep
Effects of chronic Delta(9)-tetrahydrocannabinol treatment on hippocampal extracellular acetylcholine concentration and alternation performance in the T-maze.
2001 Sep
Opioid and cannabinoid modulation of precipitated withdrawal in delta(9)-tetrahydrocannabinol and morphine-dependent mice.
2001 Sep
Neuroprotection by Delta9-tetrahydrocannabinol, the main active compound in marijuana, against ouabain-induced in vivo excitotoxicity.
2001 Sep 1
Antitumor effects of ajulemic acid (CT3), a synthetic non-psychoactive cannabinoid.
2001 Sep 15
Fast confirmation of 11-nor-9-carboxy-Delta(9)-tetrahydrocannabinol (THC-COOH) in urine by LC/MS/MS using negative atmospheric-pressure chemical ionisation (APCI).
2001 Sep 15
R(+)-methanandamide induces cyclooxygenase-2 expression in human neuroglioma cells via a non-cannabinoid receptor-mediated mechanism.
2001 Sep 7
Hu 210: a potent tool for investigations of the cannabinoid system.
2001 Summer
Patents

Sample Use Guides

In Vivo Use Guide
Appetite Stimulation: Initially, 2.5 mg capsules should be administered orally twice daily, before lunch and supper. For patients unable to tolerate this 5 mg/day dosage, the dosage can be reduced to 2.5 mg/day, administered as a single dose in the evening or at bedtime. Antiemetic: it is best administered at an initial dose of 5 mg/m2, given 1 to 3 hours prior to the administration of chemotherapy, then every 2 to 4 hours after chemotherapy is given, for a total of 4 to 6 doses/day. Should the 5 mg/m2 dose prove to be ineffective, and in the absence of significant side effects, the dose may be escalated by 2.5 mg/m2 increments to a maximum of 15 mg/m2 per dose.
Route of Administration: Oral
Substance Class Chemical
Created
by admin
on Tue Oct 22 19:48:53 UTC 2019
Edited
by admin
on Tue Oct 22 19:48:53 UTC 2019
Record UNII
M67MK6J9X0
Record Status Validated (UNII)
Record Version
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Name Type Language
DRONABINOL HEMISUCCINATE
Common Name English
Code System Code Type Description
PUBCHEM
76967311
Created by admin on Tue Oct 22 19:48:53 UTC 2019 , Edited by admin on Tue Oct 22 19:48:53 UTC 2019
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ACTIVE MOIETY