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品質等級
化驗
≥96% (HPLC)
光學活性
[α]/D +8.7°, c = 4 in chloroform(lit.)
藥物控制
regulated under CDSA - not available from Sigma-Aldrich Canada
儲存條件
desiccated
protect from light
under inert gas
濃度
5 mg/mL in absolute ethanol
儲存溫度
−20°C
SMILES 字串
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 密鑰
SQKRUBZPTNJQEM-FQPARAGTSA-N
基因資訊
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.
特點和優勢
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.
訊號詞
Danger
危險聲明
危險分類
Eye Irrit. 2 - Flam. Liq. 2
儲存類別代碼
3 - Flammable liquids
水污染物質分類（WGK）
WGK 2
閃點（°F）
57.2 °F
閃點（°C）
14 °C
個人防護裝備
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
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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