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Merck
CN

M186

Sigma-Aldrich

R(+)-甲酰胺

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

别名:

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

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关于此项目

经验公式（希尔记法）:
C23H39NO2
化学文摘社编号:
157182-49-5
分子量:
361.56
EC 号:
200-578-6
MDL编号:
MFCD00467914
UNSPSC代码:
12352200
PubChem化学物质编号:
24896698

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方案

≥96% (HPLC)

旋光性

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

药品控制

regulated under CDSA - not available from Sigma-Aldrich Canada

储存条件

desiccated
protect from light
under inert gas

浓度

5 mg/mL in absolute ethanol

储存温度

−20°C

SMILES字符串

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

基因信息

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

生化/生理作用

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.

特点和优势

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.

象形图

FlameExclamation mark
GHS02,GHS07

警示用语：

Danger

危险声明

H225,H319

危险分类

Eye Irrit. 2 - Flam. Liq. 2

储存分类代码

3 - Flammable liquids

WGK

WGK 2

闪点(°F)

57.2 °F

闪点(°C)

14 °C

个人防护装备

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

法规信息

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历史批次信息供参考:

分析证书(COA)

Lot/Batch Number
068K46091
068K4609
087K4625
066K46082
066K46081

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Raffaele Nuzzi et al.
Frontiers in neuroscience, 11, 494-494 (2017-09-21)
Glaucoma is a common degenerative disease affecting
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
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
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
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
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