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Research tools

Taranabant

A synthetic CB1 inverse agonist, developed against obesity then abandoned for psychiatric effects.

Unscheduled
Level of detail

Harm-reduction warning

No characterised human dose: animal / in vitro data only. Effect profile, safety margin and acute toxicity are not documented in human clinical practice. Extremely potent compound: severe effects, seizures and deaths reported in the literature.

C₂₇H₂₅ClF₃N₃O₂

CAS 701977-09-5

Family
ECS pharmacological toolAntagonist or inverse agonist
Molar mass
516.00 g/mol

Updated on

In plain terms

Taranabant is a synthetic molecule developed by a pharmaceutical company to try to treat obesity. It does not come from hemp: it was designed to block the receptor on which cannabinoids normally act, in order to reduce food intake. In clinical trials it led to weight loss, but irritability, anxiety and depression were more frequent; it is no longer being developed as an obesity treatment.

Receptors and activity

Target network

CB1Inverse agonistKi = 0.1 nM · humanbinding; 0.13 and 0.27 nM according to the Pertwee 2010 compilation
  • Blocks or inhibits
  • Binds or modulates

The lower the cited value, the closer the target sits to Taranabant: one ring per factor of 100. A target with no measured value stays on the edge.

Where these targets live

Where each target has been found in humans, according to the cited studies. The map shows the target, not an effect of Taranabant.

Brain, side view
Body, front view
Blood

CB1CB1 found in 7 regions of the body

  1. Basal gangliadenseMost dense in basal ganglia outflow nuclei1
  2. CerebellumdenseVery dense in the cerebellum1
  3. HippocampusdenseVery high concentrations in the hippocampus2
  4. AmygdaladenseHigh concentrations in the amygdala2
  5. CortexpresentPresent throughout the neocortex2
  6. Adipose tissuepresentExpressed in adipose tissue3
  7. GutpresentColonic epithelium, smooth muscle and plexus4

Map sources

  1. Herkenham M et al. Cannabinoid receptor localization in brain. Proc Natl Acad Sci U S A, 1990 (new tab)
  2. Glass M et al. Cannabinoid receptors in the human brain: a detailed anatomical and quantitative autoradiographic study in the fetal, neonatal and adult human brain. Neuroscience, 1997 (new tab)
  3. Engeli S et al. Activation of the peripheral endocannabinoid system in human obesity. Diabetes, 2005 (new tab)
  4. Wright K et al. Differential expression of cannabinoid receptors in the human colon: cannabinoids promote epithelial wound healing. Gastroenterology, 2005 (new tab)

Cited values

  1. CB1Inverse agonistKi = 0.1 nM · human98 out of 100

    Fong et al., J Pharmacol Exp Ther 2007 (new tab) · binding; 0.13 and 0.27 nM according to the Pertwee 2010 compilation

  2. CB2Binding (function not established)Ki = 170 nM · human46 out of 100

    Pertwee et al., Pharmacol Rev 2010 (table 1) (new tab) · binding; 170 and 310 nM according to the Pertwee 2010 compilation (approximately 1,000-fold selectivity for CB1)

Bar length follows the measured value (Ki, Kd, EC50 or IC50), on one scale shared by every entry, from 100 µM to 0.1 nM. A target with no cited value has no bar.

Pharmacology

Taranabant (MK-0364) is a selective inverse agonist of the CB1 receptor. Unlike a simple antagonist, it lowers the constitutive activity of the receptor in addition to preventing endocannabinoid binding. Its affinity for human CB1 is of the order of a tenth of a nanomolar (Ki of 0.13 nM), with a selectivity of about a thousand-fold against CB2. Partial occupancy of brain CB1 receptors, of the order of 10 to 40%, is enough to reduce food intake and to increase energy expenditure and fat oxidation (Addy et al. 2008). In the 104-week trial, the change in weight at 52 weeks was −2.6 kg on placebo, −6.6 kg at 2 mg and −8.1 kg at 4 mg (Aronne et al. 2010), but the incidence of gastrointestinal, nervous and psychiatric adverse events was higher and the 6 mg and then 4 mg doses were discontinued. Taranabant is no longer being developed as an antiobesity agent (Koch et al. 2010); no marketing authorisation was found.

Key sources.

History

Source
An entirely synthetic molecule. Taranabant exists neither in cannabis nor in any other plant. It was designed by medicinal chemistry at Merck & Co. as a drug candidate against obesity, in the wave of research opened by rimonabant on blockade of the CB1 receptor.

Origin

Research tool

No biosynthetic pathway. Taranabant is an acyclic amide obtained by total organic synthesis, with no plant precursor and no cannabinoid intermediate.

Classification

Family, origin and source verification

Family

ECS pharmacological tool › Antagonist or inverse agonist

Verification

Classification, sources and binding values checked on 20 October 2026; text read against its sources and Wikipedia.

Wikipedia (English)

Taranabant (new tab)

Article paired by the molecule's structure (InChIKey), revision read on 19 October 2026. Read as a second opinion, never cited as a source.

References

  1. Lin LS et al., J Med Chem 2006: discovery of MK-0364 (new tab)PMID 17181138
  2. Fong TM et al., J Pharmacol Exp Ther 2007: anti-obesity efficacy of MK-0364 in rodents (CB1 Ki 0.13 nM; 30 to 40% occupancy) (new tab)PMID 17327489
  3. Addy C et al., Cell Metab 2008: weight loss through increased energy expenditure and reduced caloric intake (PET CB1 occupancy of about 10 to 40%) (new tab)PMID 18177726
  4. Addy C et al., J Clin Pharmacol 2008: safety, tolerability, pharmacokinetics and pharmacodynamics, single dose (new tab)PMID 18258750
  5. Addy C et al., J Clin Pharmacol 2008: repeated doses in healthy volunteers (new tab)PMID 18508950
  6. Karanam B et al., Xenobiotica 2010: metabolism and excretion of [14C]taranabant in humans (new tab)PMID 20722472
  7. Reddy VB et al., Xenobiotica 2010: in vitro and in vivo metabolism in rats and monkeys; CYP3A4 in human microsomes (new tab)PMID 20608842
  8. Proietto J et al., Int J Obes 2010: low-dose study (new tab)PMID 20212496
  9. Aronne LJ et al., Int J Obes 2010: high-dose study (6 mg and then 4 mg doses discontinued) (new tab)PMID 20157323
  10. Morrison MF et al., Psychopharmacology 2010: smoking cessation (depression 8.2% vs 2.5%) (new tab)PMID 20191360
  11. Schoedel KA et al., J Clin Psychopharmacol 2012: abuse potential and cognitive effects (new tab)PMID 22722508
  12. Koch L, Nat Rev Endocrinol 2010: taranabant no longer developed as an anti-obesity agent (new tab)PMID 20518102
  13. Pertwee RG et al., Pharmacol Rev 2010 (IUPHAR): taranabant Ki at CB1 and CB2 (new tab)PMID 21079038
  14. PubChem CID 11226090, Taranabant (new tab)

Identifiers

Names

IUPAC name
N-[(2S,3S)-4-(4-chlorophenyl)-3-(3-cyanophenyl)butan-2-yl]-2-methyl-2-[[5-(trifluoromethyl)-2-pyridinyl]oxy]propanamide
Other names
MK-0364

Identifiers

Formula
C₂₇H₂₅ClF₃N₃O₂
CAS
701977-09-5
PubChem CID
11226090(new tab)
InChIKey
QLYKJCMUNUWAGO-GAJHUEQPSA-N
SMILES
C[C@@H]([C@@H](CC1=CC=C(C=C1)Cl)C2=CC=CC(=C2)C#N)NC(=O)C(C)(C)OC3=NC=C(C=C3)C(F)(F)F

Machine-readable entry (JSON)

LLM ingestion format: a structured superset of the entry (identifiers, binding, versioned legal status). Full corpus.