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M186

Sigma-Aldrich

R(+)-Methanandamide

5 mg/mL in absolute ethanol, ≥96% (HPLC)

Synonyme(s) :

AM-356, R(+)-Arachidonyl-1′-hydroxy-2′-propylamide

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About This Item

Formule empirique (notation de Hill):
C23H39NO2
Numéro CAS:
157182-49-5
Poids moléculaire :
361.56
Numéro CE :
200-578-6
Numéro MDL:
MFCD00467914
Code UNSPSC :
12352200
ID de substance PubChem :
24896698

Niveau de qualité

100

Pureté

≥96% (HPLC)

Activité optique

[α]/D +8.7°, c = 4 in chloroform(lit.)

Contrôle du médicament

regulated under CDSA - not available from Sigma-Aldrich Canada

Conditions de stockage

desiccated
protect from light
under inert gas

Concentration

5 mg/mL in absolute ethanol

Température de stockage

−20°C

Chaîne SMILES 

CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)N[C@H](C)CO

InChI

1S/C23H39NO2/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-23(26)24-22(2)21-25/h7-8,10-11,13-14,16-17,22,25H,3-6,9,12,15,18-21H2,1-2H3,(H,24,26)/b8-7-,11-10-,14-13-,17-16-/t22-/m1/s1

Clé InChI

SQKRUBZPTNJQEM-FQPARAGTSA-N

Informations sur le gène

mouse ... Cnr1(12801) , Cnr2(12802)
rat ... Cnr1(25248)

Actions biochimiques/physiologiques

R(+)-Methanandamide is metabolically stable congener of anandamide that has higher affinity for the cannabinoid receptor. Of the analogs tested, (R)-methanandamide exhibited the highest affinity for the cannabinoid receptor with a Ki of 20 +/- 1.6 nM, 4-fold lower than that of anandamide (Ki = 78 +/- 2 nM). (R)-methanandamide exhibits high stability to aminopeptidase hydrolysis. Experiments with mice have demonstrated that (R)-methanandamide also posseses cannabimimetric properties in vivo, as established by the four tests of hypothermia, hypokinesia, ring immobility, and antinociception.

Caractéristiques et avantages

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.

Pictogrammes

FlameExclamation mark
GHS02,GHS07

Mention d'avertissement

Danger

Mentions de danger

H225,H319

Classification des risques

Eye Irrit. 2 - Flam. Liq. 2

Code de la classe de stockage

3 - Flammable liquids

Classe de danger pour l'eau (WGK)

WGK 2

Point d'éclair (°F)

57.2 °F

Point d'éclair (°C)

14 °C

Équipement de protection individuelle

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

Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

V Abadji et al.
Journal of medicinal chemistry, 37(12), 1889-1893 (1994-06-10)
Four chiral congeners of arachidonylethanolamide (anandamide) have been synthesized and evaluated for (a) their ability to bind to the cannabinoid receptor in rat forebrain membranes and (b) their pharmacological potency as measured by the compounds' ability to inhibit electrically-evoked contractions
Raffaele Nuzzi et al.
Frontiers in neuroscience, 11, 494-494 (2017-09-21)
Glaucoma is a common degenerative disease affecting
María Gracia Gervasi et al.
PloS one, 6(2), e16993-e16993 (2011-02-25)
Anandamide (AEA), a major endocannabinoid, binds to cannabinoid and vanilloid receptors (CB1, CB2 and TRPV1) and affects many reproductive functions. Nanomolar levels of anandamide are found in reproductive fluids including mid-cycle oviductal fluid. Previously, we found that R(+)-methanandamide, an anandamide
María de Los Ángeles Nuñez-Lumbreras et al.
Frontiers in behavioral neuroscience, 14, 611780-611780 (2021-02-09)
Cannabinoid receptors 1 and 2 (CB1 and CB2, respectively) play an important role in maintaining the integrity of the blood-brain barrier (BBB). On the other hand, BBB dysfunction is a common feature in drug-resistant epilepsy. The focus of the present
Ana Inés Salazar et al.
Molecular human reproduction, 23(7), 500-508 (2017-05-02)
What is the role of the endocannabinoid system (eCS) on the lipopolysaccharide (LPS) effects on uterine explants from 7-day pregnant mice in a murine model of endotoxin-induced miscarriage? We found evidence for cannabinoid receptor type2 (CB2) involvement in LPS-induced increased
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