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Synthetic

AM356Methanandamide (AM-356)

A synthetic analogue of anandamide, resistant to hydrolysis, a selective CB1 agonist confined to the laboratory.

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.

C₂₃H₃₉NO₂

CAS 157182-49-5

Family
Synthetic CB receptor agonistResearch ligand or medicine
Molar mass
361.60 g/mol

Updated on

In plain terms

Methanandamide is a laboratory molecule: it exists neither in hemp nor in the human body. Chemists designed it as a copy of anandamide, a molecule the body makes and destroys very quickly. This copy resists the degrading enzyme far better, which makes it a research tool, not a product meant for consumption.

Receptors and activity

Target network

CB1AgonistKi = 20 nM · rat[3H]CP-55,940 displacement, rat forebrain membranes, in the presence of PMSF (anandamide: 78 nM in the same assay); IUPHAR range 17.9–28.3 nM
  • Activates
  • Blocks or inhibits

The lower the cited value, the closer the target sits to AM356: 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 AM356.

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. CB1AgonistKi = 20 nM · rat62 out of 100

    Abadji et al. 1994 · J Med Chem 37:1889 (new tab) · [3H]CP-55,940 displacement, rat forebrain membranes, in the presence of PMSF (anandamide: 78 nM in the same assay); IUPHAR range 17.9–28.3 nM

  2. CB2AgonistKi = 815 nM · mouse35 out of 100

    Khanolkar et al. 1996 · J Med Chem 39:4515 (new tab) · [3H]CP-55,940 displacement, mouse spleen membranes (other study: 868 nM)

  3. GPR55Agonistno measured value cited
  4. TASK-1 (K2P3.1)InhibitorIC50 = 100 nM · human50 out of 100

    Bedoya et al. 2019, J Med Chem (review « TASK Channels Pharmacology ») (new tab) · human TASK-1 expressed in COS cells, whole-cell patch-clamp (value taken from a review, primary source not opened)

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

Methanandamide (AM-356) is the chiral α-methylated analogue of anandamide, described in 1994 by Abadji and colleagues among four chiral congeners. In that study, the (R) enantiomer had the highest cannabinoid affinity, with a Ki of 20 ± 1.6 nM in rat forebrain membranes versus 78 ± 2 nM for anandamide, and the four compounds inhibited the electrically evoked contraction of the mouse vas deferens in the same order of potency as their affinities. In mice, it was active in the four tests of the cannabinoid tetrad: hypothermia, hypokinesia, ring immobility and antinociception (Abadji et al. 1994). Its metabolic stability was later quantified: hydrolysis by rat brain microsomal amidohydrolase reaches only 2.4% of that of anandamide, versus 23% for the (S) enantiomer (Lang et al. 1999). Its CB2 affinity remains low (815 to 868 nM, mouse spleen). Other targets have been reported: the GPR55 receptor (Lauckner et al. 2008) and the TASK-1 potassium channel. In human neuroglioma cells, it increased cyclooxygenase-2 expression in a concentration-dependent way, through a mechanism independent of cannabinoid receptors (Ramer et al. 2001). All this pharmacology is preclinical: no clinical trial has been published.

Key sources.

History

Source
Synthetic: no natural occurrence reported, in cannabis or in human tissue. A laboratory reagent.

Origin

Laboratory synthesis

None: a synthetic analogue of anandamide bearing a methyl group of R configuration on the carbon attached to the nitrogen. Described here by chemical class only.

Classification

Family, origin and source verification

Family

Synthetic CB receptor agonist › Research ligand or medicine

Class

eicosanoid

Verification

Every fact on this entry was checked against its primary sources on 20 October 2026.

Wikipedia (English)

Methanandamide (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. Abadji et al. 1994 · J Med Chem 37:1889 (new tab)PMID 8021930
  2. Khanolkar et al. 1996 · J Med Chem 39:4515 (new tab)PMID 8893848
  3. Lang et al. 1999 · J Med Chem 42:896 (amidohydrolase specificity) (new tab)PMID 10072686
  4. Lauckner et al. 2008 · PNAS 105:2699 (GPR55) (new tab)PMID 18263732
  5. Ramer et al. 2001 · Biochem Biophys Res Commun 286:1144 (COX-2) (new tab)PMID 11527419
  6. Gardiner et al. 2009 · Br J Pharmacol 158:1143 (new tab)PMID 19702785
  7. Christie et al. 2020 · J Physiol 598:139 (new tab)PMID 31642519

Identifiers

Names

Common name
Methanandamide (AM-356)
IUPAC name
(5Z,8Z,11Z,14Z)-N-[(2R)-1-hydroxypropan-2-yl]icosa-5,8,11,14-tetraenamide
Other names
AM-356 · arachidonyl-1'-hydroxy-2'-propylamide

Identifiers

Formula
C₂₃H₃₉NO₂
CAS
157182-49-5
PubChem CID
6321351(new tab)
ChEBI
CHEBI:167729(new tab)
InChIKey
SQKRUBZPTNJQEM-FQPARAGTSA-N
SMILES
CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)N[C@H](C)CO

Machine-readable entry (JSON)

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