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R(+)-ARACHIDONYL-1'-HYDROXY-2'-PROPYLAMIDE

Product Name
R(+)-ARACHIDONYL-1'-HYDROXY-2'-PROPYLAMIDE
CAS No.
157182-49-5
Chemical Name
R(+)-ARACHIDONYL-1'-HYDROXY-2'-PROPYLAMIDE
Synonyms
AM 356;R-2 METHANANDAMIDE;R-1 METHANANDAMIDE;(R)-METHANANDAMIDE;R(+)-METHANANDAMIDE;Methanandamide (R)-(+)-;(R)-Methanandamide? (Synonyms: AM-356);(R)-ARACHIDONIC ACID PROPAN-1-OL-2-AMIDE;(R)-(+)-Methanandamide (ethanol solution);R(+)-ARACHIDONYL-1'-HYDROXY-2'-PROPYLAMIDE
CBNumber
CB2780041
Molecular Formula
C23H39NO2
Formula Weight
361.56
MOL File
157182-49-5.mol
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R(+)-ARACHIDONYL-1'-HYDROXY-2'-PROPYLAMIDE Property

Boiling point:
529.0±50.0 °C(Predicted)
Density 
0.935±0.06 g/cm3(Predicted)
RTECS 
JX3848000
Flash point:
14℃
storage temp. 
−20°C
solubility 
DMF: >10 mg/ml; DMSO: >30 mg/ml; Ethanol: >100 mg/ml; Ethanol:PBS (1:2): 8.5 mg/ml; PBS (pH 7.2): <100 μg/ml
pka
14.51±0.10(Predicted)
form 
Colorless oil.
color 
Colorless to light yellow
optical activity
[α]/D +8.7°, c = 4 in chloroform(lit.)
Sensitive 
Air & Light Sensitive
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Safety

Hazard Codes 
F
Risk Statements 
11
Safety Statements 
7-16
RIDADR 
UN 1170 3/PG 2
WGK Germany 
1
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H225Highly Flammable liquid and vapour

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P337+P313IF eye irritation persists: Get medical advice/attention.

P403+P235Store in a well-ventilated place. Keep cool.

P405Store locked up.

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N-Bromosuccinimide Price

Cayman Chemical
Product number
90070
Product name
R-1 Methanandamide
Purity
≥98%
Packaging
5mg
Price
$51
Updated
2024/03/01
Cayman Chemical
Product number
90070
Product name
R-1 Methanandamide
Purity
≥98%
Packaging
10mg
Price
$92
Updated
2024/03/01
Cayman Chemical
Product number
90070
Product name
R-1 Methanandamide
Purity
≥98%
Packaging
25mg
Price
$178
Updated
2024/03/01
Cayman Chemical
Product number
90070
Product name
R-1 Methanandamide
Purity
≥98%
Packaging
50mg
Price
$330
Updated
2024/03/01
TRC
Product number
M225775
Product name
(R)-Methanandamide
Packaging
250mg
Price
$990
Updated
2021/12/16
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R(+)-ARACHIDONYL-1'-HYDROXY-2'-PROPYLAMIDE Chemical Properties,Usage,Production

Description

R-1 methanandamide is a potent cannabinoid (CB) receptor 1 agonist in the methanandamide series. It is selective for CB1 over CB2 receptors with Ki values ranging from 17.9 to 28.3 and 815 to 868 nM, respectively. R-1 methanandamide is more potent than arachidonoyl ethanolamide (AEA; ). In addition, R-1 methanandamide is more resistant than AEA to hydrolytic inactivation by fatty acid amide hydrolase (FAAH).

Uses

Methanandamide is a metabolically stable endocannabinoid analogue of the mammalian brain ligand Anandamide. Methanandamide is known to improve myocardial resistance against arrhythmogenic effects and can also be used to modulate behaviors caused by Amphetamine (HCl: A634248).

Definition

ChEBI: Methanandamide is a fatty amide.

Biological Activity

Stable anandamide analog that is a selective agonist for the CB 1 receptor (K i values are 20 and 815 nM for CB 1 and CB 2 receptors respectively). Also displays agonist activity at vanilloid receptors. Also available in water-soluble emulsion ((R)-N-(2-Hydroxy-1-methylethyl)-5Z,8Z,11Z,14Z-eicosatetraenamide ) and as part of the Cannabinoid CB 1 Receptor Tocriset™ .

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.

References

[1] PERTWEE R. Pharmacology of Cannabinoid Receptor Ligands[J]. Current medicinal chemistry, 1999, 1 1. DOI: 10.2174/0929867306666220401124036
[2] VASILIKI ABADJI. (R)-Methanandamide: A Chiral Novel Anandamide Possessing Higher Potency and Metabolic Stability[J]. Journal of Medicinal Chemistry, 1994, 37 12: 1889-1893. DOI: 10.1021/jm00038a020

R(+)-ARACHIDONYL-1'-HYDROXY-2'-PROPYLAMIDE Preparation Products And Raw materials

Raw materials

Preparation Products

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R(+)-ARACHIDONYL-1'-HYDROXY-2'-PROPYLAMIDE Suppliers

China 14 Germany 3 Japan 1 Switzerland 2 Ukraine 1 United Kingdom 4 United States 6 USA 1 Global 32
3B Pharmachem (Wuhan) International Co.,Ltd.
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821-50328103-801 18930552037
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86-21-50328109
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3bsc@sina.com
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China
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Sigma-Aldrich
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021-61415566 800-8193336
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orderCN@merckgroup.com
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China
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Shanghai EFE Biological Technology Co., Ltd.
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021-65675885 18964387627
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021-65675885
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info@efebio.com
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China
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Tianjin Kailiqi Biotechnology Co., Ltd.
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15076683720
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022-23754520
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klq@cw-bio.com
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China
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ChemeGen(Shanghai) Biotechnology Co.,Ltd.
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18818260767
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QQ 3610331285
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sales@chemegen.com
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Energy Chemical
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021-58432009 400-005-6266
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marketing1@energy-chemical.com
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Shanghai Maclean Biochemical Technology Co., LTD
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021-021-50706066 15221275939
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shenlinxing@macklin.cn
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China
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Enzo Biochem Inc
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Enzo Biochem Inc. 13797054060
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Enzoname@qq.com
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China
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Merck KGaA
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21-20338288
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ordercn@merckgroup.com
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China
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Santa Cruz Biotechnology Inc
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021-60936350
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scbt@scbt.com
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China
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Guangzhou Dedou Life Science Co., Ltd
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CHINA
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Absin Bioscience Inc.
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CHINA
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Shanghai Hao Zhun Biological Technology Co., Ltd.
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Guangzhou WeiBo Chemical Co., Ltd.
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weibochem@163.com
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6187
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157182-49-5, R(+)-ARACHIDONYL-1'-HYDROXY-2'-PROPYLAMIDERelated Search:

Arachidonyl-2′-chloroethylamide hydrate NOLADIN ETHER MEAD ACID ETHANOLAMIDE ACEA AM 630 2-AG BML-190 ACPA 5-(1,1-DIMETHYLHEPTYL)-2-[5-HYDROXY-2-(3-HYDROXYPROPYL)CYCLOHEXYL]PHENOL ARACHIDONIC ACID-(2-AMINOETHYL)-ESTER HYDROCHLORIDE AM 251 ARACHIDONAMIDE R(+)-ARACHIDONYL-1'-HYDROXY-2'-PROPYLAMIDE S(-)-ARACHIDONYL-1'-HYDROXY-2'-PROPYLAMIDE

  • AM 356
  • (R)-METHANANDAMIDE
  • R(+)-METHANANDAMIDE
  • (R)-N-(2-HYDROXY-1-METHYLETHYL)-5Z,8Z,11Z,14Z-EICOSATETRAENAMIDE
  • N-(2-HYDROXY-1R-METHYLETHYL)-5Z,8Z,11Z,14Z-EICOSATETRAENAMIDE
  • N-(2R-HYDROXYPROPYL)-5Z,8Z,11Z,14Z-EICOSATETRAENAMIDE
  • R-1 METHANANDAMIDE
  • R-2 METHANANDAMIDE
  • (R)-ARACHIDONIC ACID PROPAN-1-OL-2-AMIDE
  • (R)-(+)-ARACHIDONOYL-1'-HYDROXY-2'-PROPYLAMIDE
  • (R)-(-)-ARACHIDONOYL-2'-HYDROXY-1'-PROPYLAMIDE
  • R(+)-ARACHIDONYL-1'-HYDROXY-2'-PROPYLAMIDE
  • R(+)-METHANANDAMIDE >96% CONGENER OF ANA NDAMID
  • Methanandamide (R)-(+)-
  • (R)-(+)-Methanandamide (in Tocrisolve(TM) 100)
  • (R)-(+)-Methanandamide (in Tocrisolve 100)
  • (5Z,8Z,11Z,14Z)-N-[(2R)-1-hydroxypropan-2-yl]icosa-5,8,11,14-tetraenamide
  • (R)-(+)-Methanandamide (ethanol solution)
  • 5,8,11,14-Eicosatetraenamide, N-[(1R)-2-hydroxy-1-methylethyl]-, (5Z,8Z,11Z,14Z)-
  • (R)-Methanandamide? (Synonyms: AM-356)
  • 157182-49-5
  • C23H39NO2
  • Cannabinoid receptor
  • Cannabinoid