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M186

R(+)-Methanandamide

Name: R(+)-Methanandamide
Brand: SIGMA

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

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):

C₂₃H₃₉NO₂

CAS Number:

157182-49-5

Molecular Weight:

361.56

EC Number:

200-578-6

MDL number:

MFCD00467914

UNSPSC Code:

12352200

PubChem Substance ID:

24896698

Quality Level

100

Assay

≥96% (HPLC)

optical activity

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

drug control

regulated under CDSA - not available from Sigma-Aldrich Canada

storage condition

desiccated
protect from light
under inert gas

concentration

5 mg/mL in absolute ethanol

storage temp.

−20°C

SMILES string

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

InChI key

SQKRUBZPTNJQEM-FQPARAGTSA-N

Gene Information

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

Biochem/physiol Actions

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.

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.

Pictograms

GHS02,GHS07

Signal Word

Danger

Hazard Statements

H225,H319

Precautionary Statements

P210 - P233 - P240 - P241 - P242 - P305 + P351 + P338

Hazard Classifications

Eye Irrit. 2 - Flam. Liq. 2

Storage Class Code

3 - Flammable liquids

WGK

WGK 2

Flash Point(F)

57.2 °F

Flash Point(C)

14 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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